Mice were screened for olfactory deficits using an odor-cross habituation test (Fig 1A )(Sundberg et al., 1982 (link); Wilson and Linster, 2008 (link)). Odors (n=7; limonene, ethyl valerate, isoamyl acetate, pentanol, heptanone, propyl butyrate and nonane; Sigma Aldrich, St. Louis, MO) were diluted 1×10−3 in mineral oil and applied to a cotton-applicator stick which was then enclosed in a piece of odorless plastic tubing to prevent contact of the liquid odor with the testing chamber or animal yet still allow volatile odor delivery. Notably, such an odor presentation method controls for the influence of visual and/or somatosensory influences on odor investigation. Odors were delivered for 4 successive trials (1 block), 20sec each, separated by 30sec inter-trial intervals, by inserting the odor stick into a port on the side of the animal’s home cage (Fig 1A ). Home cage testing was chosen over testing in a separate apparatus to minimize potential influences of stress and anxiety (due to the new environment/context) on the behavioral measures. Testing took place during the light phase of the animals’ (12:12) day: light cycle, over two daily sessions (3–4 odors/session) separated by 24–48 hrs. The duration of time spent investigating, defined as snout-oriented sniffing within 1cm of the odor presentation port, was recorded across all trials by a single observer blind to genotypes (D.W.W.). Home cages were cleaned with fresh corn cob bedding 24–48hrs prior to behavioral testing to reduce unnecessary background odors, yet still allowing for adaptation to the new bedding. The stainless steel food bin and water bottle were removed from cages immediately prior to testing.
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Chemicals & Drugs
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Organic Chemical
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Nonane
Nonane
Nonane is a straight-chain alkane hydrocarbon with the chemical formula C9H20.
It is a clear, colorless, volatile liquid with a faint, petrol-like odor.
Nonane is commonly used as a solvent, fuel additive, and chemical intermediate in a variety of industrial applications.
Researching the properties, synthesis, and applications of nonane can provide valuable insights for fields such as chemistry, materials science, and energy production.
PubCompare.ai's AI-driven platform can help optimize your nonane research by effortlessly locating the best protocols from literature, preprints, and patents, and providing comparison tools to boost reproducibility and accurrracy, ensuring your nonane experiments are a success.
It is a clear, colorless, volatile liquid with a faint, petrol-like odor.
Nonane is commonly used as a solvent, fuel additive, and chemical intermediate in a variety of industrial applications.
Researching the properties, synthesis, and applications of nonane can provide valuable insights for fields such as chemistry, materials science, and energy production.
PubCompare.ai's AI-driven platform can help optimize your nonane research by effortlessly locating the best protocols from literature, preprints, and patents, and providing comparison tools to boost reproducibility and accurrracy, ensuring your nonane experiments are a success.
Most cited protocols related to «Nonane»
Acclimatization
Animals
Anxiety
Butyrates
ethyl valerate
Food
Genotype
Gossypium
isoamyl acetate
Light
Limonene
Maize
Mice, House
nonane
Obstetric Delivery
Odors
Oil, Mineral
Sense of Smell
Stainless Steel
Visually Impaired Persons
The quantitative analyses were run in the same GC instrument as the qualitative ones, configured with a Flame Ionization Detector (FID) and equipped with an Agilent Technologies 7683 series autoinjector (Little Falls, DE, USA).
The analytical conditions were the same described for the qualitative analyses, but with a different thermal program. In fact, with DB-5ms column, the initial temperature of 50 °C was kept for 1 min, followed by a thermal gradient of 3 °C/min until 180 °C, then a second thermal gradient of 15 °C/min until 250 °C. The final temperature was maintained for 15 min. For what concerns the analysis on HP-INNOWax, the same GC method as DB-5ms was applied, except for the final temperature that only reached 230 °C. The FID was alimented with a mixture of hydrogen and air, at the flow of 30 mL/min and 300 mL/min respectively. The detector was set at the temperature of 250 °C. In order to quantify the analytes, a relative response factor (RRF) was calculated for each component, according to the respective combustion enthalpy [37 (link),38 (link)]. In this respect, A. Chaintreau and colleagues demonstrated that the RRF of an organic compound, analyzed by FID, only depends, with good approximation, on its molecular formula and number of aromatic rings. According to this principle, they described a mathematical formula [38 (link)], that permits to estimate the RRF toward a quantification standard (usually methyl octanoate). In our case, a modified method was actually applied, since isopropyl caproate was used instead of methyl octanoate and two calibration curves (one for each column) have been used instead of a single point internal standard. The isopropyl caproate was prepared by synthesis in one of the authors’ laboratory (G.G.) and its purity was calculated by GC as 97%. For calibration curves construction, six calibration standard dilutions were prepared, dissolving 0.6, 1.8, 4.3, 8.3, 16.8, and 34.3 mg of isopropyl caproate in 10 mL of cyclohexane respectively. As usual, an amount of 7.0 mg of n-nonane was used as internal standard inside each dilution. Both calibration curves generated a correlation coefficient of 0.995.
The analytical conditions were the same described for the qualitative analyses, but with a different thermal program. In fact, with DB-5ms column, the initial temperature of 50 °C was kept for 1 min, followed by a thermal gradient of 3 °C/min until 180 °C, then a second thermal gradient of 15 °C/min until 250 °C. The final temperature was maintained for 15 min. For what concerns the analysis on HP-INNOWax, the same GC method as DB-5ms was applied, except for the final temperature that only reached 230 °C. The FID was alimented with a mixture of hydrogen and air, at the flow of 30 mL/min and 300 mL/min respectively. The detector was set at the temperature of 250 °C. In order to quantify the analytes, a relative response factor (RRF) was calculated for each component, according to the respective combustion enthalpy [37 (link),38 (link)]. In this respect, A. Chaintreau and colleagues demonstrated that the RRF of an organic compound, analyzed by FID, only depends, with good approximation, on its molecular formula and number of aromatic rings. According to this principle, they described a mathematical formula [38 (link)], that permits to estimate the RRF toward a quantification standard (usually methyl octanoate). In our case, a modified method was actually applied, since isopropyl caproate was used instead of methyl octanoate and two calibration curves (one for each column) have been used instead of a single point internal standard. The isopropyl caproate was prepared by synthesis in one of the authors’ laboratory (G.G.) and its purity was calculated by GC as 97%. For calibration curves construction, six calibration standard dilutions were prepared, dissolving 0.6, 1.8, 4.3, 8.3, 16.8, and 34.3 mg of isopropyl caproate in 10 mL of cyclohexane respectively. As usual, an amount of 7.0 mg of n-nonane was used as internal standard inside each dilution. Both calibration curves generated a correlation coefficient of 0.995.
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Anabolism
Cyclohexane
factor A
Flame Ionization
hexanoate
Hydrogen
methyl octanoate
nonane
Organic Chemicals
Technique, Dilution
The qualitative chemical analyses were performed with a gas chromatography-mass spectrometry (GC-MS) system, constituted by an Agilent Technologies gas chromatograph 6890N coupled to a simple quadrupole Mass Spectrometry Detector (MSD) model 5973 (Santa Clara, CA, USA). The MSD was operated in SCAN mode, with an electronic ionization source of 70 eV. The ion detection was limited to the range of 35–350 m/z. The transfer line was set at the temperature of 280 °C, the MS ion source at 200 °C. The gas chromatograph was configurated with a DB-5ms non-polar (5%-phenyl-methylpolysiloxane, 30 m, 0.25 mm internal diameter, and 0.25 μm film thickness; J & W Scientific, Folsom, CA, USA) and a HP-INNOWax polar (polyethylene glycol, 30 m, 0.25 mm internal diameter and 0.25 μm film thickness; Agilent Technologies, Santa Clara, CA, USA) capillary columns.
The GC-MS analyses on DB-5ms were performed as follow: the carrier gas was helium, set at constant flow, with a rate of 1 mL/min. All the chromatographic runs were performed injecting 1 μL. The injector was set in split mode (40:1), with an injection temperature of 250 °C. The elution was conducted from 50 °C (1 min) to 250 °C (10 min) at a gradient rate of 3 °C/min.
The same conditions and thermal program were used for the analyses on HP-INNOWax, except for the final temperature, that just reached 230 °C due to the lower thermal stability of the stationary phase.
In order to identify the components of the EO, the linear retention index (LRI) of each constituent was calculated according to Van Den Dool and Kratz [36 (link)] and compared to literature, together with the corresponding mass spectrum (seeTable 1 ). LRIs were calculated through the homologous series of linear alkanes, using a mixture from n-nonane to n-pentacosane (n-nonane purity was 99% from BDH, Dubai, UAE. C10–C25 purity was 99% from Sigma-Aldrich, St. Louis, MO, USA).
The GC-MS analyses on DB-5ms were performed as follow: the carrier gas was helium, set at constant flow, with a rate of 1 mL/min. All the chromatographic runs were performed injecting 1 μL. The injector was set in split mode (40:1), with an injection temperature of 250 °C. The elution was conducted from 50 °C (1 min) to 250 °C (10 min) at a gradient rate of 3 °C/min.
The same conditions and thermal program were used for the analyses on HP-INNOWax, except for the final temperature, that just reached 230 °C due to the lower thermal stability of the stationary phase.
In order to identify the components of the EO, the linear retention index (LRI) of each constituent was calculated according to Van Den Dool and Kratz [36 (link)] and compared to literature, together with the corresponding mass spectrum (see
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Alkanes
Capillaries
Chromatography
Gas Chromatography
Gas Chromatography-Mass Spectrometry
Helium
Mass Spectrometry
n-pentacosane
nonane
Polyethylene Glycols
Radionuclide Imaging
Retention (Psychology)
Z 350
All organic solvents were HPLC grade (except nonane, which was 99% pure reagent grade) and purchased from Thermo Fisher Scientific (Waltham, MA, USA). Labeled d7-cholesterol was purchased from Sigma-Aldrich (USA). Cholesteryl-d7-palmitate was purchased from Avanti Polar Lipids, (Alabaster, AL, USA). Labeled d98-tripalmitin was purchased from CDN Isotopes, (Pointe-Claire, Quebec, Canada). Two serum reference materials, SRM 1951c Level 1 and Level 2, were provided by the National Institute of Standards and Technology (NIST, Gaithersburg, MD, USA). Five value assigned reference materials (701, 707, 713, 801, and 813) were provided by the Lipid Standardization Program (LSP) at the Centers for Disease Control (CDC). Four units of frozen human serum from de-identified individuals were purchased from Interstate Blood Bank (Memphis, TN, USA) and were used for the preparation of a quality control (QC) pool. After mixing, the pool was distributed into 1 mL aliquots and stored at –80 °C. The 32 de-identified serum samples from normolipidemic (N = 11), hypercholesterolemic (N = 6), hypertriglyceridemic (N = 9), and hyperlipidemic donors (N = 6) were purchased frozen from Bioreclamation IVT (New York City, NY, USA), stored at –80 °C until analysis. All individual donor samples were viral tested before shipment.
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Alabaster
Cholesterol
cholesteryl palmitate
Donors
Freezing
High-Performance Liquid Chromatographies
Homo sapiens
Isotopes
Lipids
nonane
Serum
Solvents
Tissue Donors
tripalmitin
A set of twelve metal-oxide semiconducting films has been selected for the purpose. The materials chosen are five solid solutions of SnO2 and TiO2 (ST20 650, ST25 650, ST25 + Au1%, ST30 650, ST50 650), a solid solution of WO3 and SnO2 (WS30), a solution of TiO2, Ta2O5 and vanadium oxide (TiTaV) and, finally, a solution of SnO2, TiO2 and Nb2TiO7 (STN). For a better understanding, the metal oxide composition of sensors is reported in Table 1 .
Generally, the presence of SnO2 makes the active material sensitive to a wide range of gases, so the addition of other oxides is fundamental to refine the selectivity of the sensors. Functional materials were prepared by the sol-gel technique [17 ], then fired at the temperatures indicated at the end of their names and used to screen-print sensing layers onto miniaturized alumina substrates [18 ]. Afterwards, they were characterized with the X-ray diffraction technique (XRD), thermo-gravimetry/differential thermal analysis (TG/DTA) and scanning electron microscopy (SEM). Details about the synthesis of these materials and the deposition technique have been reported in previous works of our group [19 –22 ]. Sensors were positioned inside a sealed test chamber (Figure 1 ), and conductance measurements were performed with the so-called “flow-through technique” [23 ,24 ]. The flow-rate is measured in sccm (standard cubic centimeters per minute), and it affects the rate of the surface reactions between the gas and the surface of the sensitive material.
To identify the best detecting temperature for each type of sensing material, we tested the response at several working temperatures (300 °C, 350 °C, 400 °C, 450 °C, 500 °C, 550 °C, 600 °C, 650°C). Temperatures lower than 300°C are not taken into account, because, at low temperatures, the metal-oxide sensors used in this work do not show a stable response. The working temperatures are set by applying an external voltage Vh to the heating circuit of each sensor, whose resistance is indicated here with Rh. Therefore, it is possible to control and directly modify Rh, which determines the sensor's temperature. The temperature of the chamber (36–37°C) is directly influenced by the sensors working temperatures and remains almost constant. We performed this temperature analysis in dry conditions (synthetic dry air with 20% of O2 and 80% of N2) with the following target gases: C6H6 (2 ppm), CH4 (50 ppm), NO (5 ppm), and we made some interfering tests also with H2 (60 ppm) and humidity. CO2 is not considered, because it is well known that it is hardly detected by chemoresistive sensors [19 ]. For methane T=300°C was not considered, because is too low for sensors to generate a response. Dry conditions were chosen to show the absolute response to the gases of interest; in fact, even if humidity is present in our intestine, generally diminishing the sensors response, it does not conspicuously change the response ratios between benzene and its interferers. Measurements in wet conditions are in progress and not presented here. The results are summarized inFigures 2 , 3 and 4 .
The concentrations chosen for interferers are based on the fact that we want to be able to detect benzene even in the unfortunate case that the gut is filled with fermentation products. Therefore, CH4 and NO are tested with a greater concentration than that of benzene. On the other hand, when a gastrointestinal exam occurs, normally, the patient has to take a particular diet some days before the test, in order to reduce the amount of disturbing gaseous compounds inside the intestine. Then, some interference tests were made. We tested C6H6 + CH4 at the best temperature for benzene, derived from the previous analysis.
After selecting the most sensitive materials for benzene, we tested them in dry conditions with C6H6 + H2 (2, 60 ppm) C6H6 + H2 + CH4 (2, 60, 10 ppm) and C6H6 + H2 + CH4 (2, 60, 10 ppm) using humidity as an interferer (RH = 37%).
In the second part, the same analysis is performed with the VOC, 1-iodo-nonane (chemical formula: C9H19I [25 ]), with the apparatus shown inFigure 5 . We obtained the responses as a function of the temperature shown in Figure 6 .
Tests were done in wet conditions (with a constant relative humidity (RH) ∼18% inside the volume of the chamber) to reproduce the intestinal environment. A fixed fraction of the total flux came from the gas bubbler filled with distilled water, while the remaining fraction was composed of two lines, one of synthetic dry air and the other passing through a second gas bubbler in which there were some drops of 1-iodononane. After the stabilization of sensors in wet air, a drop of 1-iodo-nonane is put inside the gas bubbler after being weighed with a precision balance (accuracy of 10−5g). After the measurement, the concentration has been calculated, dividing the quantity of 1-iodo-nonane, just measured before, by the evaporation time, taking into account also the volume of 1-iodo-nonane in the chamber and the volume of the chamber itself. The characteristics of 1-iodo-nonane used for the tests are listed inTable 2 .
Generally, the presence of SnO2 makes the active material sensitive to a wide range of gases, so the addition of other oxides is fundamental to refine the selectivity of the sensors. Functional materials were prepared by the sol-gel technique [17 ], then fired at the temperatures indicated at the end of their names and used to screen-print sensing layers onto miniaturized alumina substrates [18 ]. Afterwards, they were characterized with the X-ray diffraction technique (XRD), thermo-gravimetry/differential thermal analysis (TG/DTA) and scanning electron microscopy (SEM). Details about the synthesis of these materials and the deposition technique have been reported in previous works of our group [19 –22 ]. Sensors were positioned inside a sealed test chamber (
To identify the best detecting temperature for each type of sensing material, we tested the response at several working temperatures (300 °C, 350 °C, 400 °C, 450 °C, 500 °C, 550 °C, 600 °C, 650°C). Temperatures lower than 300°C are not taken into account, because, at low temperatures, the metal-oxide sensors used in this work do not show a stable response. The working temperatures are set by applying an external voltage Vh to the heating circuit of each sensor, whose resistance is indicated here with Rh. Therefore, it is possible to control and directly modify Rh, which determines the sensor's temperature. The temperature of the chamber (36–37°C) is directly influenced by the sensors working temperatures and remains almost constant. We performed this temperature analysis in dry conditions (synthetic dry air with 20% of O2 and 80% of N2) with the following target gases: C6H6 (2 ppm), CH4 (50 ppm), NO (5 ppm), and we made some interfering tests also with H2 (60 ppm) and humidity. CO2 is not considered, because it is well known that it is hardly detected by chemoresistive sensors [19 ]. For methane T=300°C was not considered, because is too low for sensors to generate a response. Dry conditions were chosen to show the absolute response to the gases of interest; in fact, even if humidity is present in our intestine, generally diminishing the sensors response, it does not conspicuously change the response ratios between benzene and its interferers. Measurements in wet conditions are in progress and not presented here. The results are summarized in
The concentrations chosen for interferers are based on the fact that we want to be able to detect benzene even in the unfortunate case that the gut is filled with fermentation products. Therefore, CH4 and NO are tested with a greater concentration than that of benzene. On the other hand, when a gastrointestinal exam occurs, normally, the patient has to take a particular diet some days before the test, in order to reduce the amount of disturbing gaseous compounds inside the intestine. Then, some interference tests were made. We tested C6H6 + CH4 at the best temperature for benzene, derived from the previous analysis.
After selecting the most sensitive materials for benzene, we tested them in dry conditions with C6H6 + H2 (2, 60 ppm) C6H6 + H2 + CH4 (2, 60, 10 ppm) and C6H6 + H2 + CH4 (2, 60, 10 ppm) using humidity as an interferer (RH = 37%).
In the second part, the same analysis is performed with the VOC, 1-iodo-nonane (chemical formula: C9H19I [25 ]), with the apparatus shown in
Tests were done in wet conditions (with a constant relative humidity (RH) ∼18% inside the volume of the chamber) to reproduce the intestinal environment. A fixed fraction of the total flux came from the gas bubbler filled with distilled water, while the remaining fraction was composed of two lines, one of synthetic dry air and the other passing through a second gas bubbler in which there were some drops of 1-iodononane. After the stabilization of sensors in wet air, a drop of 1-iodo-nonane is put inside the gas bubbler after being weighed with a precision balance (accuracy of 10−5g). After the measurement, the concentration has been calculated, dividing the quantity of 1-iodo-nonane, just measured before, by the evaporation time, taking into account also the volume of 1-iodo-nonane in the chamber and the volume of the chamber itself. The characteristics of 1-iodo-nonane used for the tests are listed in
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Most recents protocols related to «Nonane»
Example 37
Tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate (419 mg, 1.85 mmol), 4-fluoronitrobenzene (261 mg, 1.85 mmol) and potassium carbonate (511 mg, 3.70 mmol) were stirred in DMF (5.00 mL) at 90° C. overnight. 30 mL water was added. The resulting solid was filtered and washed with water then air dried overnight to provide tert-butyl 7-(4-nitrophenyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate (606 mg, 94.2%). LCMS: C18H25N3O4 requires 347, found: m/z=348 [M+H]+.
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4-nitrophenyl
Anabolism
Lincomycin
nonane
potassium carbonate
TERT protein, human
Example 38
Tert-butyl 7-(4-nitrophenyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate (606 mg, 1.74 mmol) and 10% Pd/C (50 mg, mmol) were stirred in EtOH (3.00 mL) and ethyl acetate (3.00 mL) under a balloon of H2. After 2 hours, 10% Pd/C (50 mg, mmol) was added. The mixture stirred under a balloon of H2 overnight then was filtered through a plug of celite and concentrated to provide tert-butyl 7-(4-aminophenyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate (545 mg, 98.4%). LCMS: C18H27N3O2 requires 317, found: m/z=318 [M+H]+.
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4-nitrophenyl
Anabolism
Celite
Ethanol
ethyl acetate
Lincomycin
nonane
TERT protein, human
Example 40
Tert-butyl 7-[4-({3-cyano-6-[(3R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl]pyrazin-2-yl}amino)phenyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate (258 mg, 0.43 mmol) was dissolved in MeOH (6.00 mL) and DMSO (3.00 mL). Cesium carbonate (140 mg, 0.43 mmol) and 1 mL 35% H2O2 were added. After 1 hour, 3 mL ACN was added. After 5 minutes, the mixture got hot. Water and ethyl acetate were added. The organic layer was washed with 2 more portions of water. The organic layer was dried over Na2SO4 and concentrated to provide tert-butyl 7-[4-({3-carbamoyl-6-[(3R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl]pyrazin-2-yl}amino)phenyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate (267 mg, 100%). LCMS: C32H45N9O4 requires 619, found: m/z=620 [M+H]+.
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Anabolism
cesium carbonate
ethyl acetate
Lincomycin
nonane
Peroxide, Hydrogen
Sulfoxide, Dimethyl
TERT protein, human
Example 39
3-Chloro-5-[(3R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl]pyrazine-2-carbonitrile (209 mg, 0.65 mmol), tert-butyl 7-(4-aminophenyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate (207 mg, 0.65 mmol), and cesium carbonate (0.85 g, 2.61 mmol) were deposited in a vial with dioxane (6.00 mL). A vacuum was pulled on the vial until the mixture bubbled and the headspace was backfilled with argon 5 times. Palladium (II) acetate (29 mg, 0.13 mmol) and BINAP (81 mg, 0.13 mmol) were added. A vacuum was pulled on the vial and the headspace was backfilled with argon for 5 cycles. The mixture was heated at 90° C. overnight. Water was added and the mixture was extracted twice with DCM. The combined organic layers were concentrated then purified by flash chromatography on a 24 g column eluted with 0 to 10% MeOH/ethyl acetate to provide tert-butyl 7-[4-({3-cyano-6-[(3R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl]pyrazin-2-yl}amino)phenyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate (258 mg, 65.8%). LCMS: C32H43N9O3 requires 601, found: m/z=602 [M+H]+.
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Acetate
Anabolism
Argon
BINAP
cesium carbonate
Chromatography
Dioxanes
ethyl acetate
Lincomycin
nonane
Palladium
Pyrazines
TERT protein, human
Vacuum
In a 200-mL two-necked round-bottomed
flask equipped
with a magnetic stirring bar, a rubber septum and an argon balloon,
NaH (60% dispersion in mineral oil, 6.24 g, 156 mmol), and THF (30
mL) were added, respectively. The reaction mixture was stirred, and
nonane-1,9-diol (4.17 g, 26.0 mmol) in THF (30 mL) was added. The
reaction mixture was warmed to reflux and stirred for 12 h. Then,
the reaction mixture was cooled to 0 °C, and 2-bromohexanoic
acid5a (7.63 mL, 54.6 mmol) was added slowly to this
reaction mixture. The reaction mixture was warmed to reflux and stirred
for 48 h. After the reaction, the reaction mixture was cooled to 0
°C and ice water (100 mL) was added to quench the reaction. The
whole mixture was extracted with 1 M NaOH (5 × 10 mL). Then,
the pH was adjusted to 1 with 2 M H2SO4 solution.
The whole mixture was extracted with diethyl ether (5 × 10 mL).
The combined organic phases were washed with H2O (20 mL),
dried (with Na2SO4), and concentrated in vacuo
to give a crude product. In a 100-mL one-necked round-bottomed flask
equipped with a magnetic stirring bar and a rubber septum, crude product,
EtOH (20 mL), and MeSNa aq (15 wt %, 20 mL) were added, respectively.
The reaction mixture was warmed to 40 °C and stirred for 24 h.
After the reaction, the reaction mixture was concentrated in vacuo,
and the pH was adjusted to 1 with 2 M H2SO4 solution.
The whole mixture was extracted with diethyl ether (5 × 10 mL).
The combined organic phases were washed with H2O (20 mL),
dried (with Na2SO4), and concentrated in vacuo
to give the crude product. The crude product was purified by flash
column chromatography on silica gel (n-hexane/ethyl
acetate/acetic acid = 7:3:0.1) to give the title compound7d (5.41 g, 54%). Colorless oil; 1H NMR (500 MHz, CDCl3) δ 11.13 (brs, 2H), 3.86 (dd, J =
4.9, 7.6 Hz, 2H), 3.66–3.58 (m, 2H), 3.39 (t, J = 7.6 Hz, 1H), 3.37 (t, J = 7.6 Hz, 1H), 1.83–1.73
(m, 4H), 1.65–1.57 (m, 4H), 1.46–1.28 (m, 18H), 0.91
(t, J = 7.2 Hz, 6H); 13C{1H}
NMR (126 MHz, CDCl3) δ 178.8, 78.6, 70.9, 32.3, 29.5,
29.3, 29.1, 27.2, 25.8, 22.2, 13.7; IR (neat) 3451, 3146, 2931, 2859,
1721, 1467, 1335, 1284, 1208, 1130, 1102, 987, 730 cm–1; HRMS (EI) m/z: [M-CHO2]+ calcd for C20H39O4 343.2848, found 343.2850.
flask equipped
with a magnetic stirring bar, a rubber septum and an argon balloon,
NaH (60% dispersion in mineral oil, 6.24 g, 156 mmol), and THF (30
mL) were added, respectively. The reaction mixture was stirred, and
nonane-1,9-diol (4.17 g, 26.0 mmol) in THF (30 mL) was added. The
reaction mixture was warmed to reflux and stirred for 12 h. Then,
the reaction mixture was cooled to 0 °C, and 2-bromohexanoic
acid
reaction mixture. The reaction mixture was warmed to reflux and stirred
for 48 h. After the reaction, the reaction mixture was cooled to 0
°C and ice water (100 mL) was added to quench the reaction. The
whole mixture was extracted with 1 M NaOH (5 × 10 mL). Then,
the pH was adjusted to 1 with 2 M H2SO4 solution.
The whole mixture was extracted with diethyl ether (5 × 10 mL).
The combined organic phases were washed with H2O (20 mL),
dried (with Na2SO4), and concentrated in vacuo
to give a crude product. In a 100-mL one-necked round-bottomed flask
equipped with a magnetic stirring bar and a rubber septum, crude product,
EtOH (20 mL), and MeSNa aq (15 wt %, 20 mL) were added, respectively.
The reaction mixture was warmed to 40 °C and stirred for 24 h.
After the reaction, the reaction mixture was concentrated in vacuo,
and the pH was adjusted to 1 with 2 M H2SO4 solution.
The whole mixture was extracted with diethyl ether (5 × 10 mL).
The combined organic phases were washed with H2O (20 mL),
dried (with Na2SO4), and concentrated in vacuo
to give the crude product. The crude product was purified by flash
column chromatography on silica gel (n-hexane/ethyl
acetate/acetic acid = 7:3:0.1) to give the title compound
4.9, 7.6 Hz, 2H), 3.66–3.58 (m, 2H), 3.39 (t, J = 7.6 Hz, 1H), 3.37 (t, J = 7.6 Hz, 1H), 1.83–1.73
(m, 4H), 1.65–1.57 (m, 4H), 1.46–1.28 (m, 18H), 0.91
(t, J = 7.2 Hz, 6H); 13C{1H}
NMR (126 MHz, CDCl3) δ 178.8, 78.6, 70.9, 32.3, 29.5,
29.3, 29.1, 27.2, 25.8, 22.2, 13.7; IR (neat) 3451, 3146, 2931, 2859,
1721, 1467, 1335, 1284, 1208, 1130, 1102, 987, 730 cm–1; HRMS (EI) m/z: [M-CHO2]+ calcd for C20H39O4 343.2848, found 343.2850.
Top products related to «Nonane»
Sourced in Germany, United States, Spain, United Kingdom
Nonane is a saturated aliphatic hydrocarbon with the chemical formula C9H20. It is a colorless liquid with a mild odor. Nonane is used as a reference standard and as a solvent in various laboratory applications.
Sourced in Germany, United States, Switzerland
Decane is a straight-chain alkane hydrocarbon with the chemical formula C10H22. It is a colorless, odorless liquid that is insoluble in water. Decane is commonly used as a solvent and in the synthesis of other organic compounds.
Sourced in Germany, Spain, United States
Undecane is a straight-chain alkane hydrocarbon with the chemical formula C₁₁H₂₄. It is a colorless, odorless liquid that is commonly used in various laboratory applications.
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N-nonane is a saturated hydrocarbon with the chemical formula C₉H₂₀. It is a colorless, flammable liquid. N-nonane is commonly used as a reference standard and calibration compound in analytical chemistry applications.
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Tetradecane is a saturated aliphatic hydrocarbon with the chemical formula C14H30. It is a colorless, odorless liquid that is commonly used as a reference material and solvent in various laboratory applications.
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Hexadecane is a saturated hydrocarbon compound with the chemical formula C16H34. It is a colorless, odorless liquid at room temperature. Hexadecane is commonly used as a reference material and solvent in various laboratory applications.
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Dodecane is a straight-chain alkane with the chemical formula C12H26. It is a colorless, odorless, and flammable liquid commonly used in laboratory settings as a solvent and reagent.
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Tridecane is a chemical compound with the formula C13H28. It is a straight-chain alkane hydrocarbon. Tridecane is a colorless, volatile liquid with a mild odor.
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N-hexane is a colorless, volatile liquid chemical compound with the molecular formula C6H14. It is commonly used as a solvent in various industrial and laboratory applications due to its ability to dissolve a wide range of organic compounds.
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Limonene is a naturally occurring hydrocarbon found in the rinds of citrus fruits. It is commonly used as a solvent in laboratory settings due to its ability to dissolve a wide range of organic compounds.
More about "Nonane"
Nonane, a straight-chain alkane hydrocarbon with the formula C9H20, is a clear, colorless, and volatile liquid with a faint, petrol-like odor.
This versatile compound finds numerous applications in industry, serving as a solvent, fuel additive, and chemical intermediate.
Exploring the properties, synthesis, and uses of nonane can provide valuable insights for fields such as chemistry, materials science, and energy production.
Closely related to nonane are other alkanes like decane (C10H22), undecane (C11H24), and n-nonane (a linear isomer).
These higher-order hydrocarbons share similar characteristics and applications, often used as solvents, lubricants, and in the production of fuels and other petrochemicals.
Tetradecane (C14H30), hexadecane (C16H34), and dodecane (C12H26) are additional members of this alkane family, each with their own unique properties and use cases.
Limonene, a cyclic terpene, is another compound that shares some structural similarities with nonane and can be used as a solvent or additive.
N-hexane, a shorter-chain alkane, is also commonly employed in industrial processes and as a reference standard.
Leveraging the power of PubCompare.ai's AI-driven platform, researchers can optimize their nonane-related studies by effortlessly locating the best protocols from literature, preprints, and patents.
The platform's comparison tools help boost reproducibility and accuracy, ensuring successful nonane experiments and data-driven decision making.
This versatile compound finds numerous applications in industry, serving as a solvent, fuel additive, and chemical intermediate.
Exploring the properties, synthesis, and uses of nonane can provide valuable insights for fields such as chemistry, materials science, and energy production.
Closely related to nonane are other alkanes like decane (C10H22), undecane (C11H24), and n-nonane (a linear isomer).
These higher-order hydrocarbons share similar characteristics and applications, often used as solvents, lubricants, and in the production of fuels and other petrochemicals.
Tetradecane (C14H30), hexadecane (C16H34), and dodecane (C12H26) are additional members of this alkane family, each with their own unique properties and use cases.
Limonene, a cyclic terpene, is another compound that shares some structural similarities with nonane and can be used as a solvent or additive.
N-hexane, a shorter-chain alkane, is also commonly employed in industrial processes and as a reference standard.
Leveraging the power of PubCompare.ai's AI-driven platform, researchers can optimize their nonane-related studies by effortlessly locating the best protocols from literature, preprints, and patents.
The platform's comparison tools help boost reproducibility and accuracy, ensuring successful nonane experiments and data-driven decision making.