To a solution of the chroman-4-one (6c ) (71 mg, 0.34 mmol) in benzene (2 mL) was added isovanillin (62 mg, 0.41 mmol) and p-toluenesulfonic acid (7 mg, 0.03 mmol) at 0 °C. The reaction mixture was refluxed for 12 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (ethyl acetate : n-hexane = 1 : 1) to afford the 3-benzylidene-chroman-4-one (7c ) (72 mg, 62%). 1H-NMR (600 MHz, CDCl3) δ 7.72 (s, 1H), 6.89-6.87 (m, 2H), 6.83 (d, 1H, J = 8.4Hz), 6.11 (s, 1H), 6.06 (s, 1H), 5.23 (s, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 3.82 (s, 3H); 13C-NMR (150 MHz, CDCl3) δ 179.5, 165.6, 164.6, 162.7, 147.4, 145.5, 135.7, 130.5, 128.3, 123.0, 115.8, 110.5, 107.3, 9305, 93.5, 67.6, 56.1, 56.0, 55.5; HRMS (EI): mass calcd for C19H18O6 [M+], 342.1103; found, 342.1101.
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4-toluenesulfonic acid
4-toluenesulfonic acid
4-Toluenesulfonic acid is a commonly used organic compound with a variety of applications in research and industry.
This sulfonic acid derivative of toluene is known for its ability to act as a catalyst, pH adjuster, and reagent in numerous chemical reactions and processes.
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By leveraging AI-driven comparisons, users can identify the best products and protocols for their specific needs, streamlining their research and experencing the future of scientific inquiry.
This sulfonic acid derivative of toluene is known for its ability to act as a catalyst, pH adjuster, and reagent in numerous chemical reactions and processes.
PubCompare.ai's AI-powered platform can help researchers easily locate protocols, preprints, and patents related to 4-toluenesulfonic acid, allowing them to optimize their workflow and make informed decisions.
By leveraging AI-driven comparisons, users can identify the best products and protocols for their specific needs, streamlining their research and experencing the future of scientific inquiry.
Most cited protocols related to «4-toluenesulfonic acid»
1H NMR
4-toluenesulfonic acid
Benzene
Carbon-13 Magnetic Resonance Spectroscopy
Chromans
Chromatography
ethyl acetate
isovanillin
n-hexane
Pressure
Silica Gel
mPEG–ABCPA–mPEG
macro-initiators were synthesized through an esterification of mPEG
(molecular weight, 2.0 or 5.0 kDa) and ABCPA, using DCC as a coupling
reagent and 4-(dimethylamino)pyridinium 4-toluenesulfonate (DPTS,
which was made by separately dissolving DMAP and p-toluenesulfonic acid in tetrahydrofuran (THF) and mixing the two
solutions using a 1:1 molar equivalence) as a catalyst (Scheme 1 ).29 (link) ABCPA (1 equiv), mPEG (2 equiv), and DPTS (0.3 equiv) (or 0.280
g of ABCPA, 10 g of mPEG, 0.094 g of DPTS) were dissolved in 50 mL
of dry dichloromethane (DCM) and put on ice. Next, 3 equiv of DCC
(0.619 g of DCC) were dissolved in 50 mL of DCM and dropwise added
to the mPEG solution under nitrogen atmosphere. After addition of
DCC, the ice bath was removed allowing the reaction mixture to reach
room temperature. After 16 h at room temperature, the reaction mixture
was filtered to remove the precipitated 1,3-dicyclohexyl urea and
the solvent was removed in vacuo. The product was dissolved in water,
stirred for 2 h, and dialyzed against water for 72 h at 4 °C.
The sample was freeze-dried to obtain a fluffy white product.
The product was analyzed by
GPC using a PSS PFG analytical linear
S column and PEGs of narrow molecular weights as calibration standards,
as described previously. Samples were prepared by dissolving approximately
5 mg of the MI in 1 mL of dimethylformamide (DMF) containing 10 mM
LiCl. Samples of 20 μL were injected, the eluent was DMF containing
10 mM LiCl, the elution rate was 0.7 mL/min, the temperature was 40
°C, and detection was done using a refractive index detector.30 (link)The product was further analyzed by 1H NMR spectroscopy
(20 mg product was dissolved in 700 μL CDCl3). To
determine the unreacted mPEG-OH content, TAIC was added to the sample
and analyzed again after 20 min using 1H NMR spectroscopy.
After reaction with TAIC, the signal of the methylene group neighboring
the terminal hydroxyl group shifts from 4.2 to 4.4 ppm and the amount
of unreacted mPEG-OH can subsequently be determined based on the peak
areas.31 (link),32 (link)
macro-initiators were synthesized through an esterification of mPEG
(molecular weight, 2.0 or 5.0 kDa) and ABCPA, using DCC as a coupling
reagent and 4-(dimethylamino)pyridinium 4-toluenesulfonate (DPTS,
which was made by separately dissolving DMAP and p-toluenesulfonic acid in tetrahydrofuran (THF) and mixing the two
solutions using a 1:1 molar equivalence) as a catalyst (
g of ABCPA, 10 g of mPEG, 0.094 g of DPTS) were dissolved in 50 mL
of dry dichloromethane (DCM) and put on ice. Next, 3 equiv of DCC
(0.619 g of DCC) were dissolved in 50 mL of DCM and dropwise added
to the mPEG solution under nitrogen atmosphere. After addition of
DCC, the ice bath was removed allowing the reaction mixture to reach
room temperature. After 16 h at room temperature, the reaction mixture
was filtered to remove the precipitated 1,3-dicyclohexyl urea and
the solvent was removed in vacuo. The product was dissolved in water,
stirred for 2 h, and dialyzed against water for 72 h at 4 °C.
The sample was freeze-dried to obtain a fluffy white product.
The product was analyzed by
GPC using a PSS PFG analytical linear
S column and PEGs of narrow molecular weights as calibration standards,
as described previously. Samples were prepared by dissolving approximately
5 mg of the MI in 1 mL of dimethylformamide (DMF) containing 10 mM
LiCl. Samples of 20 μL were injected, the eluent was DMF containing
10 mM LiCl, the elution rate was 0.7 mL/min, the temperature was 40
°C, and detection was done using a refractive index detector.30 (link)The product was further analyzed by 1H NMR spectroscopy
(20 mg product was dissolved in 700 μL CDCl3). To
determine the unreacted mPEG-OH content, TAIC was added to the sample
and analyzed again after 20 min using 1H NMR spectroscopy.
After reaction with TAIC, the signal of the methylene group neighboring
the terminal hydroxyl group shifts from 4.2 to 4.4 ppm and the amount
of unreacted mPEG-OH can subsequently be determined based on the peak
areas.31 (link),32 (link)
1H NMR
4-(1-(4-azidobenzamidomethyl)ethenyl)-2-carboxypyrrolidin-3-ylacetic acid
4-toluenesulfonic acid
Atmosphere
Bath
carbene
Dimethylformamide
diphenylthiosulfinate
Esterification
Freezing
G 619
Hydroxyl Radical
Methylene Chloride
Molar
monomethoxypolyethylene glycol
Nitrogen
Solvents
Spectroscopy, Nuclear Magnetic Resonance
Spectrum Analysis
tetrahydrofuran
Urea
4-(Dimethylamino)pyridine
(DMAP), p-toluenesulfonic acid, 4,4-azobis(4-cyanopentanoic
acid)
(ABCPA),dl -1-amino-2-propanol, methacryloyl chloride, benzoyl
chloride, poly(ethylene glycol) methyl ether (mPEG) 2 kDa, N,N′-dicyclohexylcarbodiimide (DCC),
trichloroacetyl isocyanate (TAIC), bovine serum albumin, and pyrene
were obtained from Sigma-Aldrich (Darmstadt, Germany) and used without
further purification. mPEG 5 kDa was obtained from Polysciences (Warrington)
and dried in a vacuum oven overnight at 70 °C. EasiVial PEG standards
for gel permeation chromatography (GPC) analysis were obtained from
Agilent (Santa Clara). All solvents were purchased from commercial
suppliers and used as received.
(DMAP), p-toluenesulfonic acid, 4,4-azobis(4-cyanopentanoic
acid)
(ABCPA),
chloride, poly(ethylene glycol) methyl ether (mPEG) 2 kDa, N,N′-dicyclohexylcarbodiimide (DCC),
trichloroacetyl isocyanate (TAIC), bovine serum albumin, and pyrene
were obtained from Sigma-Aldrich (Darmstadt, Germany) and used without
further purification. mPEG 5 kDa was obtained from Polysciences (Warrington)
and dried in a vacuum oven overnight at 70 °C. EasiVial PEG standards
for gel permeation chromatography (GPC) analysis were obtained from
Agilent (Santa Clara). All solvents were purchased from commercial
suppliers and used as received.
4-(1-(4-azidobenzamidomethyl)ethenyl)-2-carboxypyrrolidin-3-ylacetic acid
4-toluenesulfonic acid
Dicyclohexylcarbodiimide
ethylene glycol diethyl ether
Gel Chromatography
methacryloyl chloride
monomethoxypolyethylene glycol
Poly A
Propanols
pyridine
Serum Albumin, Bovine
Solvents
trichloroacetyl isocyanate
Vacuum
p-Toluenesulfonic acid (0.11 g, 0.57 mmol) was added to a flask charged with 3-(1H-indol-3-yl)-propylamine15 (link) (0.10 g, 0.57 mmol) and 5-chloroisatin (0.12 g, 0.63 mmol) in absolute ethanol (5 mL) and heated to 100 °C. After 15 h, the reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 0.5 M NaOH and saturated aqueous NaCl. The organic layer was separated and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to provide 6 as an orange solid (17 mg, 9%). 1H NMR (300 MHz, DMSO-d6): δ 10.56 (s, 1H), 10.10 (s, 1H), 7.46 (dd, J = 7.0, 1.5 Hz, 1H), 7.32 (dd, J = 8.4, 2.2 Hz, 1H), 7.15 (m, 2H), 7.00 (dd, J = 6.9, 1.5 Hz, 1H), 6.97 (dd, J = 6.9, 1.8 Hz, 1H), 6.93 (d, J = 8.4 Hz, 1H), 3.47 (m, 2H), 3.02 (m, 3H), 1.98 (m, 2H). MS (ESI) m/z 338.0 (M + H)+.
1H NMR
4-toluenesulfonic acid
Chromatography
Ethanol
ethyl acetate
Sodium Chloride
Sulfoxide, Dimethyl
Z 338
1H NMR
4-toluenesulfonic acid
Benzene
Carbon-13 Magnetic Resonance Spectroscopy
Chromans
Chromatography
ethyl acetate
isovanillin
n-hexane
Pressure
Silica Gel
Most recents protocols related to «4-toluenesulfonic acid»
Brønsted acidic carbon materials were synthesized by one-step hydrothermal carbonization using the procedure reported by Xiao and coworkers with a little modification.58 The mixture of the d -glucose (10 g), citric acid monohydrate (4 g, 20 mmol), Brønsted acid (p-toluenesulfonic acid (TsOH), sulfuric acid (H2SO4) or hydrochloric acid (HCl), 10 mmol), and 80 mL distilled water was charged in a 100 mL Teflon-lined stainless-steel autoclave. The mixture was heated at 180 °C for 4 h in an oven. Black carbonaceous materials were obtained by filtration and washed several times with distilled water and followed by methanol, and then dried at 80 °C for 6 h. Three samples were prepared through this procedure including C–TsOH, C–H2SO4, and C–HCl, which had synthesized yields per 100 g of d -glucose of 36.3, 38.1, and 34.5 wt%, respectively.
4-toluenesulfonic acid
Acids
Carbon
Citric Acid Monohydrate
Filtration
Glucose
Hydrochloric acid
Methanol
Stainless Steel
Sulfuric Acids
Teflon
4-toluenesulfonic acid
Adipic Acids
Cellulose
Choline Chloride
Citric Acid Monohydrate
fumaric acid
Hydrochloric acid
malonic acid
Monohydrate, Glucose
Oxalic Acids
Sulfuric Acids
All reagents were analytically pure and were used immediately upon receipt. Glucose (99%), xylose (99%), tetrahydrofuran (99%), pyridine (99%), glutaraldehyde (50%), epichlorohydrin (98%), hexanediamine (99%), diphenylmethane diisocyanate (98%), and p-toluenesulfonic acid (99%) were purchased from Innochem (Shanghai, China). Dichloromethane (99%), lithium bromide (99%), furfural (99%), and phosphoric acid (75 wt%~80 wt%) were purchased from Aladdin® Chemicals (Shanghai, China); hydrochloric acid (37 wt%), acetone (99%), and ethanol (99%) were purchased from China National Pharmaceutical Group Corporation (Beijing, China). 5-hydroxymethylfurfural (HMF) was purchased from Bidepharm (Shanghai, China). Eucalyptus and masson pine (40–80 mesh) were provided by Qingshan Paper Co., Ltd. (Sanming, China), and the straw (40–80 mesh) was obtained from the State Key Laboratory of Bio-based Materials and Green Paper of Qilu University of Technology (Jinan, China).
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4,4'-diphenylmethane diisocyanate
4-toluenesulfonic acid
5-hydroxymethylfurfural
Acetone
Epichlorohydrin
Ethanol
Eucalyptus
Furaldehyde
Glucose
Glutaral
Hydrochloric acid
lithium bromide
Methylene Chloride
Pharmaceutical Preparations
Phosphoric Acids
Pinus
pyridine
tetrahydrofuran
Xylose
Preparation of adhesive: Initially, the adducts were vacuum dried at 50 °C for 24 h and then ground into a powder with a quartz mortar. About 10–20 g of the adducts was weighed with the addition of acetone (about 50% mass of the adduct) for dissolving the adduct. The mixture was stirred evenly to form a gel. Next, hydrochloric acid (HCl), phosphoric acid (PA), or p-toluenesulfonic acid (p-TsOH) was added as a curing agent, and the loading of the curing agent was about 2–15% of the mass of the adduct. Hexamethylene diamine (EDA), glutaraldehyde (GA), epichlorohydrin (ECH), or diphenylmethane diisocyanate (MDI) was added as cross-linking agents during the preparation process, and the amount of the added cross-linking agent was about 3–9% of the adhesive mass. After the addition of all additives, the mixture was fully stirred and then coated on the surface of the veneers.
Preparation of three-layer poplar plywood: The poplar veneer was cut into several sheets with a size of 100 mm × 300 mm × 1.6 mm, and the moisture content of the veneers were between 8% and 15%. The grain of each layer was perpendicularly oriented with its adjacent layer. The adhesives were evenly coated on the two sides of the middle-layer veneer (Figure 2 ) by a rubber brush with a glue sizing of 270 g/m2. Prior to hot-pressing, the coated wood veneers were placed in an oven and treated at 80 °C for 8 h to remove excess acetone and prevent glue penetration. Then the three-layer poplar plywood was pressed by a laboratory-scale hot-presser (KS100H, Kesheng Industrial, Dongguan, China) at 120–200 °C for 5–20 min.
Preparation of three-layer poplar plywood: The poplar veneer was cut into several sheets with a size of 100 mm × 300 mm × 1.6 mm, and the moisture content of the veneers were between 8% and 15%. The grain of each layer was perpendicularly oriented with its adjacent layer. The adhesives were evenly coated on the two sides of the middle-layer veneer (
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4,4'-diphenylmethane diisocyanate
4-toluenesulfonic acid
Acetone
Cereals
Cyclohexane
Diamines
Epichlorohydrin
Glutaral
Hydrochloric acid
phosphoric acid
Populus
Powder
Quartz
Rubber
Vacuum
All reagents used in this study were purchased from Sigma-Aldrich (Saint Quentin Fallavier, France) unless otherwise noted. 2,2-bis(hydroxymethyl)propionic acid (bis-MPA, 98%), p-toluenesulfonic acid monohydrate (PTSA.H2O, >98.5%), 4-(dimethylamino)pyridine (DMAP, 99%), Dowex®50WX8 hydrogen form (50–100 mesh), ethyl chloroformate (97%), 8-diazabicyclo[5.4.0]undec-7-ene (DBU, 98%), benzoic acid (99.5%), acetone (99.9%), dichloromethane (DCM, 99.5%), tetrahydrofuran (THF, 99.9%), diethyl ether (99%), methanol (CH3OH, 99.8%), water (HPLC grade), N,N-dimethyl formamide (DMF, 99.9%), diethyl (3-bromopropyl)phosphonate (95%), copper(I) bromide (CuBr, 98%), N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA, 99%), sodium azide (NaN3, 99%), and dimethyl (2-hydroxyethyl)phosphonate (95%) were purchased from Acros Organics (Geel, Belgium). 2,2-dimethoxypropane (>98%), N,N’-dicyclohexyldicarbodiimide (DCC, >98%), and triethylamine (TEA, >99%) were purchased from TCI (Zwijndrecht, Belgium). Benzyl alcohol (BnOH, 99%, Alfa Aesar, Karlsruhe, Germany) and dialysis membrane (Standard RC, 3500 Da, Spectrum Laboratories, Racho Dominguez, CA, USA) were used as received. 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 5-methyl-5-propargylxycarbonyl-1,3-dioxane-2-one (MPC) were synthesized according to the literature procedures [19 (link),20 (link),21 (link)].
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1,3,6,8-pyrene tetrasulfonate
4-toluenesulfonic acid
Acetone
Benzoic Acid
Benzyl Alcohol
Bromides
Copper
Dialysis
Dimethylformamide
dioxane
Dowex
ethyl chloroformate
Ethyl Ether
High-Performance Liquid Chromatographies
Hydrogen
Methanol
Methylene Chloride
Phosphonates
propionic acid
pyridine
Sodium Azide
tetrahydrofuran
Tissue, Membrane
triethylamine
Top products related to «4-toluenesulfonic acid»
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P-toluenesulfonic acid is a crystalline organic compound that serves as a common laboratory reagent. It is a white, crystalline solid that is soluble in water and other polar solvents. Its primary function is as an acid catalyst in various chemical reactions and processes.
Sourced in United States, Germany
P-toluenesulfonic acid monohydrate is a chemical compound used in various laboratory applications. It is a white crystalline solid with the chemical formula CH3C6H4SO3H·H2O. The compound serves as a catalyst, pH adjuster, and reagent in chemical synthesis and analysis procedures.
Sourced in United Kingdom, United States
P-toluenesulfonic acid is a chemical compound that is commonly used as a catalyst in various chemical reactions. It is a white crystalline solid with a mild aromatic odor. The compound is soluble in water, alcohols, and other organic solvents.
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Toluene is a colorless, flammable liquid with a distinctive aromatic odor. It is a common organic solvent used in various industrial and laboratory applications. Toluene has a chemical formula of C6H5CH3 and is derived from the distillation of petroleum.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
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P-toluenesulfonic acid is a chemical compound that serves as a key laboratory reagent. It functions as a catalyst, proton donor, and drying agent in various chemical processes and reactions.
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Ethanol is a clear, colorless liquid chemical compound commonly used in laboratory settings. It is a key component in various scientific applications, serving as a solvent, disinfectant, and fuel source. Ethanol has a molecular formula of C2H6O and a range of industrial and research uses.
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N,N-dimethylformamide is a clear, colorless liquid organic compound with the chemical formula (CH3)2NC(O)H. It is a common laboratory solvent used in various chemical reactions and processes.
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Dichloromethane is a clear, colorless, and volatile liquid commonly used as a laboratory solvent. It has a molecular formula of CH2Cl2 and a molar mass of 84.93 g/mol. Dichloromethane is known for its high solvent power and low boiling point, making it suitable for various laboratory applications where a versatile and efficient solvent is required.
More about "4-toluenesulfonic acid"
4-toluenesulfonic acid, p-toluenesulfonic acid, tosylic acid, p-TSA, toluene, methanol, DMSO, ethanol, N,N-dimethylformamide, dichloromethane, catalyst, pH adjuster, reagent, chemical reactions, protocols, preprints, patents, research, industry, AI-powered comparisons, workflow optimization, scientific inquiry