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Thionyl chloride

Thionyl chloride (SOCl2) is a highly reactive organosulfur compound with numerous applications in organic synthesis, including acylation, chlorination, and sulfonation reactions.
It serves as a versatile reagent for the conversion of alcohols, carboxylic acids, and other functionalities into their corresponding chloro derivatives.
Thionyl chloride is also used in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Researchers must carefully handle this corrosive and potentially hazardous substance, following appropriate safety protocols to ensure the reproducibility and reliability of their experiments.

Most cited protocols related to «Thionyl chloride»

Stable Isotope Analysis of Coastal and Terrestrial Ecosystems

Cited 7 times

All of the marine and terrestrial samples were collected in 2001–2013 from a stony shore and a farm in Yugawara (35°08′N, 139°07′E), Japan, respectively. The stony shoreline surveyed represented ∼0.2 hectares and ranged in depth from 0 to 5 m, where brown and red macroalgae are dominant primary producers but seagrass is absent. The farm was also approximately 0.2 hectares with cultivation of fruits and vegetables, all of which were C₃ plants. Green leaves and/or nuts were collected for higher plants, and whole samples of 1–15 individuals within a single stage were collected for the other species. The collected samples were cleaned with distilled water to remove surface contaminants and stored at −20°C. For most terrestrial species and marine macroalgae, whole-organism samples were prepared for isotopic analyses. For the remaining marine specimens, small samples of muscle tissue were taken. Shell samples were taken from several gastropod and lobster specimens, and scales were dissected from most of the fish species (Appendices A1 and A2). There was no substantial effect on the trophic position estimates among these different tissue types within a single animal specimen (e.g., Chikaraishi et al. 2010 , 2011 ; Ogawa et al. 2013 ). The bulk-carbon and bulk-nitrogen isotopic compositions of representative samples (40 coastal marine and 69 terrestrial samples, Appendices A1 and A2) were determined using a Flash EA (EA1112) instrument coupled to a Delta^plusXP IRMS instrument with a ConFlo III interface (Thermo Fisher Scientific, Bremen, Germany). Carbon and nitrogen isotopic compositions are reported in the standard delta (δ) notation relative to the Vienna Peedee Belemnite (VPDB) and to atmospheric nitrogen (AIR), respectively.
The nitrogen isotopic composition of amino acids was determined by gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS) after HCl hydrolysis and N-pivaloyl/isopropyl (Pv/iPr) derivatization, according to the procedure in Chikaraishi et al. (2009 ) (which are described in greater detail at http://www.jamstec.go.jp/biogeos/j/elhrp/biogeochem/download_e.html). In brief, samples were hydrolyzed using 12 Mol/L HCl at 110°C. The hydrolysate was washed with n-hexane/dichloromethane (3/2, v/v) to remove hydrophobic constituents. Then, derivatizations were performed sequentially with thionyl chloride/2-propanol (1/4) and pivaloyl chloride/dichloromethane (1/4). The Pv/iPr derivatives of amino acids were extracted with n-hexane/dichloromethane (3/2, v/v). The nitrogen isotopic composition of amino acids was determined by GC/C/IRMS using a 6890N GC (Agilent Technologies, Palo Alto, CA) instrument coupled to a Delta^plusXP IRMS instrument via a GC-C/TC III interface (Thermo Fisher Scientific, Bremen, Germany). To assess the reproducibility of the isotope measurement and obtain the amino acid isotopic composition, reference mixtures of nine amino acids (alanine, glycine, leucine, norleucine, aspartic acid, methionine, glutamic acid, phenylalanine, and hydroxyproline) with known δ¹⁵N values (ranging from −25.9‰ to +45.6‰, Indiana University, SI science co.) were analyzed after every four to six samples runs, and three pulses of reference N₂ gas were discharged into the IRMS instrument at the beginning and end of each chromatography run for both reference mixtures and samples. The isotopic composition of amino acids in samples was expressed relative to atmospheric nitrogen (AIR) on scales normalized to known δ¹⁵N values of the reference amino acids. The accuracy and precision for the reference mixtures were always 0.0‰ (mean of Δ) and 0.4–0.7‰ (mean of 1σ) for sample sizes of ≥1.0 nmol N, respectively.
The δ¹⁵N values were determined for the following 10 amino acids: alanine, glycine, valine, leucine, isoleucine, proline, serine, methionine, glutamic acid, and phenylalanine (Appendices A1 and A2). These amino acids were chosen because their peaks were always well separated with baseline resolution in the chromatogram (Chikaraishi et al. 2009 ). Also, it should be noted that glutamine was quantitatively converted to glutamic acid during acid hydrolysis; as a result, the α-amino group of glutamine contributed to the δ¹⁵N value calculated for glutamic acid.
The TP_Glu/Phe value (and its potential uncertainty calculated by taking into account the propagation of uncertainty on each factor in the Eq. (1)) was calculated from the observed δ¹⁵N values (as 1σ = 0.5‰) of glutamic acid and phenylalanine in the organisms of interest, using eq. (1) with the β value of −3.4 ± 0.9‰ for coastal marine and +8.4 ± 1.6‰ for terrestrial samples, and with the TDF value of 7.6 ± 1.2‰ for both ecosystems, according to Chikaraishi et al. (2009 , 2010 , 2011 ). The TP_Tr/Scr values were not calculated, because we did not measure the δ¹⁵N values of lysine and tyrosine for all investigated samples and of serine for approximately a half of samples.

Chikaraishi Y., Steffan S.A., Ogawa N.O., Ishikawa N.F., Sasaki Y., Tsuchiya M, & Ohkouchi N. (2014). High-resolution food webs based on nitrogen isotopic composition of amino acids. Ecology and Evolution, 4(12), 2423-2449.

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Publication 2014

1-Propanol Acids Alanine Amino Acids Animals Aspartic Acid Calculi Carbon Chromatography derivatives Dietary Fiber Ecosystem Embryophyta Fishes Fruit Gas Chromatography-Mass Spectrometry Gastropods Glutamic Acid Glutamine Glycine Hexanes Histocompatibility Testing Hydrolysis Hydroxyproline Isoleucine Isotopes Leucine Lysine Marines Methionine Methylene Chloride Muscle Tissue Nitrogen Nitrogen Isotopes Norleucine Nuts Phenylalanine pivaloyl chloride Plants Proline Pulses Seaweed Serine Specimen Collection thionyl chloride Tyrosine Valine Vegetables

Synthesis of Krytox-PEG Copolymer Emulsion Stabilizer

Cited 6 times

The copolymer used to stabilize the primary emulsion (W₁/PFC) was synthesized using a two-step process, as seen in Fig. 1 and outlined in Holtze et al. (38 (link)). First, Krytox 157 FSL (DuPont, Wilmington, DE, USA) – a perfluoroether with carboxylic acid functionality – was converted to an acid chloride using methods previously described (39 , 40 ). Briefly, under a nitrogen purge, Krytox 157 FSL was added to a round bottom flask containing HFE-7100 (3M, St. Paul, MN, USA), a mixture of methyl nonafluoroisobutyl ether and methyl nonafluorobutyl ether. Thionyl chloride (Sigma Aldrich, St. Louis, MO, USA) was then added in a 10:1 molar excess relative to the Krytox 157 FSL. The flask was refluxed with a condenser and stirred for 24 hours at 50°C while under a nitrogen purge. The resulting mixture was concentrated using a rotary evaporator. Second, the acid chloride was reacted with polyoxyethylene (PEG) diamine (Sigma Aldrich) to form a copolymer, analogous to previously described methods (39 , 40 ). The solvent was a 5:3 volumetric ratio of HFE-7100 and benzotrifluoride (Alfa Aesar, Ward Hill, MA, USA). Similar experimental conditions were used as in the first reaction step. The resulting copolymer, termed Krytox-PEG copolymer, was concentrated using a rotary evaporator and its structure was confirmed using ¹H, ¹³C, and ¹⁹F NMR spectroscopy.

Fabiilli M.L., Lee J.A., Kripfgans O.D., Carson P.L, & Fowlkes J.B. (2010). DELIVERY OF WATER-SOLUBLE DRUGS USING ACOUSTICALLY-TRIGGERED, PERFLUOROCARBON DOUBLE EMULSIONS. Pharmaceutical Research, 27(12), 2753-2765.

Publication 2010

Acids benzotrifluoride Carboxylic Acids Chlorides Diamines Emulsions Ethers HFE-7100 Molar Nitrogen Polyethylene Glycols Solvents Spectroscopy, Nuclear Magnetic Resonance thionyl chloride Training Programs Vision

Efficient Radiosynthesis of PET Tracers [11C]WAY-100635 and [11C]-(+)-PHNO

Cited 6 times

In-loop−¹¹C-carboxylation: 80 cm polyethylene (PE)-tubing was coiled into a loop and equipped with two Luer-fittings. Loops were coated with a mixture of one of the three respective Grignard reagents (500 µL) or diethyl ether (as negative control) in THF (1000 µL) for comparison reasons. Therefore, the respective diluted Grignard solution was pushed through the loop and completely drained by a smooth He-stream (5 mL/min). (note: Grignard reagents were purchased as solutions in diethyl ether). The inlet of the loop was connected immediately after impregnation to the line from the molecular sieve CO₂ trap and the outlet to an Ascarite II trap to collect unreacted [¹¹C]CO₂. Upon delivery from the cyclotron, [¹¹C]CO₂ was transported to the hot cell and trapped on-line within the molecular sieve. Subsequently, it was released by heating the trap to 400 °C and the gas was passed to the previously impregnated loop using a smooth stream of helium (3–5 mL/min). Excess of unreacted [¹¹C]CO₂ (or not combined ¹¹C-intermediates) was retained within the Ascarite II trap. The bound ¹¹C-acylation synthon was swept out of the loop using a mixture of THF (400 µL) and thionyl chloride (5 µL).
[Carbonyl-¹¹C]WAY-100635: Precursor compound, WAY-100634, and reference compound, WAY 100635, were obtained from ABX-Advanced Biochemical Compounds (Radeberg, Germany). Semi-preparative HPLC: column: Phenomenex^® Gemini, 10 µm 110 A, 250×10 mm²; mobile phase: methanol/0.1 M ammonium formate (70/30) (v/v%) plus 3 mL TEA per liter; 8 mL/min; analytical HPLC: column: Waters^® µ-Bondapak C-18 (5 µm, 300×3.9 mm² WAT027324) mobile phase: 0.1 M ammonium formate/ACN (55/45 v/v%); 2 mL/min.
Up-scaled [carbonyl-¹¹C]WAY-100635 production was performed according to Wadsak et al. (2007) with modifications due to the implementation of a new TRACERlab^™ FX C pro synthesizer. Briefly, loop was coated by pushing a cyclohexane magnesium chloride solution (0.5 mL) in THF (1 mL) through the PE-tubing equipped with Luer-fittings. Radioactivity was trapped nearly quantitatively and converted on-line to magnesium chloride cyclohexane [¹¹C]carboxylate. Using a thionyl chloride solution (5 µL in 400 µL THF), the Grignard reaction intermediate was converted to the respective carboxylic acid chloride, swept out the loop and transferred into the reactor vial containing precursor (WAY-100634, 3.4–3.6 mg) in TEA (20 µL) and THF (50 µL). Resulting reaction mixture was heated up to 70 °C for 4 min, cooled down to room temperature and quenched with water (1 mL). Crude reaction mixture was automatically transferred and injected to the semi-preparative HPLC system triggered by a fluid detector. Product peak was collected (6–8 mL) and diluted (80 mL water) within the bulb and passed through an SPE (C-18 plus) column. After complete transfer, the column was washed with water (10 mL) and the purified product was eluted with 1.5 mL ethanol and 5 mL 0.9% saline solution. For final formulation, further 9 mL saline solution 0.9%, 1 mL saline solution 3% and 1 mL phosphate buffer (125 mM) were added, transferred to a lead shielded laminar-air-flow hot cell and sterile-filtered on-line.
[¹¹C]-(+)-PHNO: Precursor compound, (+)-HNO hydrochloride, and reference compound, (+)-PHNO, were obtained from ABX-Advanced Biochemical Compounds (Radeberg, Germany). Semi-preparative HPLC: column: Phenomenex^® Luna C18(2), 10 µm, 250×10 mm²; mobile phase: 25 mM PBS (pH 7.0)/acetonitrile (ACN) (60/40 v/v%); 6 mL/min); analytical HPLC: LichroCART^® Lichrospher 100, RP-18 (5 µm, 4×250 mm²) with LichroCART^® Lichrospher RP-18 guard column (5 µm, 4×4 mm²), mobile phase: 10 mM PBS (pH 7.0)/ACN (60/40 v/v%); 1.5 mL/min).
The [¹¹C]-(+)-PHNO-radiosynthesis is outlined in Scheme 1. The first reaction step in the synthesis sequence, the Grignard reaction, was performed on the basis of the previously described production of [carbonyl-¹¹C]WAY-100635 adopting the loop method. In this case, the PE-loop was coated with ethyl magnesium bromide (500 µL) in THF (1000 µL) for the conversion to magnesium bromide [¹¹C]propionate. Using thionyl chloride solution (5 µL in 400 µL THF), the built [¹¹C]propionic acid chloride was transferred directly into the reaction vessel containing (+)-HNO (2.5 mg) suspended in TEA (50 µL) and THF (400 µL). The resulting reaction mixture was heated to 80 °C for 5 min. After cooling down to −15 °C, LiAlH₄ (120 µL) in THF (400 µL) was added to the reaction intermediate (i.e. [¹¹C]1-((4αR,10βR)-9-hydroxy-5,6-dihydro-2H-naphtho[1,2-β][1,4]oxazin-4(3 H,4αH,10βH)-yl)propan-1-one) and subsequently heated up to 80 °C for 2 min. Subsequently, THF was evaporated completely within 2 min and the reaction mixture was cooled to 45 °C. Crude [¹¹C]-(+)-PHNO was dissolved in 1 M HCl (800 µL) and neutralized with 1 M sodium hydroxide solution (800 µL) prior to injection onto semi-preparative HPLC. The HPLC fraction containing purified [¹¹C]-(+)-PHNO was collected (7–9 mL), diluted with water (70 mL) and passed through a C-18 Sep-Pak^® plus cartridge. Further workup procedure and formulation of the final product were identical to the described [carbonyl–¹¹C]WAY-100635 method (see above).

Rami-Mark C., Ungersboeck J., Haeusler D., Nics L., Philippe C., Mitterhauser M., Willeit M., Lanzenberger R., Karanikas G, & Wadsak W. (2013). Reliable set-up for in-loop 11C-carboxylations using Grignard reactions for the preparation of [carbonyl-11C]WAY-100635 and [11C]-(+)-PHNO. Applied Radiation and Isotopes, 82, 75-80.

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Publication 2013

Synthesis of 5-Hydroxy-2-Methyl-4-Oxopyran-3-Carboxamides

Cited 4 times

All reagents and solvents
were obtained from commercial sources and used without further purification.
All reactions, unless otherwise stated, were performed under a nitrogen
atmosphere. Reactions were monitored using either aluminum or glass-backed
silica TLC plates impregnated with a fluorescent indicator, absorbing
at 254 nm. Silica gel column chromatography was performed on a CombiFlash
Rf Teledyne ISCO system using hexane, ethyl acetate, methylene chloride,
or methanol as eluent. Reverse phase column chromatography (C18 column)
was performed on the same instrument using 0.1% formic acid in methanol,
acetonitrile, or water as eluent. Separations were monitored by mass
spectrometry via a Teledyne ISCO RF⁺ PurIon ESI-MS or APCI-MS
detector with 1 Da resolution. The purity of all compounds used in
assays was determined to be ≥95% by ¹H NMR spectroscopy
and confirmed by high-resolution mass spectrometry (HRMS) experiments
using an Agilent 6230 Accurate-Mass LC-TOFMS located in the University
of California, San Diego, Molecular Mass Spectrometry Facility (MMSF).
Standard resolution MS was performed at either the aforementioned
MMSF or Teledyne ISCO RF⁺ PurIon MS. Microwave reactions
were performed using a CEM Discover series S-class microwave reactor
in pressure-sealed vessels. Docking simulations were performed using
MOE, version 2014.0901. Flexible receptor modeling (induced fit) was
employed in these simulations, and metal-binding atoms were fixed.
Synthesis of 5-hydroxy-2-methyl-4-oxo-4H-pyran-3-carboxamide
derivatives is outlined in Scheme 1. Bromopyruvic acid was transformed to bromodiethoxypropanoic
acid by treatment with triethyl orthoformate in the presence of catalytic
sulfuric acid. The acetal-protected propanoic acid was then activated
as the p-nitrophenyl ester 74. Pyrone
ring formation was achieved over two steps by the slow addition of 74 to a solution of ethyl or tert-butyl acetoacetate
that was previously deprotonated by sodium hydride. After the initial
nucleophilic attack of the activated ester by the acetoacetate, ring
closing was accomplished via nucleophilic addition by heating the
reaction mixture to reflux for 4–6 h. The pyrone-acetal 75a was deesterified by stirring briefly with trifluoroacetic
acid (TFA) in CH₂Cl₂. The tert-butyl ester was removed selectively by controlling the time of the
reaction, as the ester is more labile in the absence of water than
the acetal. Key intermediate 76 was used to prepare various
amides using analogous conditions; specifically, 76 was
activated with HATU and triethylamine in DMF. Addition of the amine
was followed by heating and stirring for ∼18 h at 60 °C.
After isolation of the formed amide the acetal was deprotected in
water and acid to reveal the 3-keto intermediate, which rapidly tautomerizes
to form the desired 3-hydroxide species.
To acquire SAR at the 6-position, a library of amine derivatives
was prepared from commercially available kojic acid (Scheme 2). The phenolic oxygen of 8 was selectively protected as a benzyl ether by treatment
with benzyl bromide in the presence of potassium carbonate in DMF
at 80 °C. Compound 78 was prepared quantitatively
by reacting 77 with thionyl chloride. Nucleophilic addition
of various primary and secondary amines followed by selective hydrolysis
of the benzyl ether in a mixture of TFA, concentrated HCl, and glacial
acetic acid afforded aminomethylpyrones in good yields. Amide
and sulfonamide derivatives were generated by the nucleophilic addition
of sodium azide to 78, followed by reduction of 79 with triphenylphosphine to afford 80 as a
key intermediate. Compound 80 was reacted with various
acid chlorides and sulfonyl chlorides to generate 28–31, after deprotection of the phenol by boron trichloride.
Preparation
of pyridinone derivatives of allomaltol (2) possessing N-aryl and -alkyl substituents is described
generally in Scheme 3. Kojic chloride (81) was derived from 8 and reduced to 2 using metallic zinc and strong acid.
While dehydration of the hydroxypyrone ring to afford hydroxypyridinone
derivatives was shown to be possible, benzyl protection of the hydroxyl
group prior to dehydration greatly improved yields and suppressed
formation of side products. Key intermediate 82 was irradiated
in a microwave reactor in the presence of excess amine and acetic
acid to produce a wide variety of pyridinone derivatives. Microwave
heating under increased pressure greatly accelerated reaction rates;
dehydration using conventional heating could be accomplished but required
refluxing reactants in ethanol for a period of days. Removal of the
benzyl ether after dehydration was shown to be accomplished quickly
and efficiently employing boron trichloride as a dealkylating agent
or less efficiently using a 5:5:1 mixture of concentrated hydrochloric
acid, glacial acetic acid, and TFA, as a milder alternative to boron
trihalides (Supporting Information).
Fragment merging
was accomplished as shown in Scheme 4. Merging of N-arylpyridinones with
5-position carboxylates began with advanced
intermediate 76a. Hydrolysis of the acetal followed by
tautomerization yielded 83. After benzyl protection of
the phenol, dehydration was accomplished with microwave heating using
dry ethanol as a solvent. Hydrolysis of only the benzyl ether using
strong acid afforded compounds 67–69 in moderate yields; hydrolysis of both ester and ether was not observed.
Further base catalyzed hydrolysis of the ethyl ester proved difficult
and ultimately resulted in the decomposition of the ring system. As
an alternative route, compound 86 was hydrolyzed to the
free carboxylic acid by stirring in 4% KOH and methanol for several
hours. This reaction proceeded almost quantitatively with no apparent
decomposition of the starting material. Compound 86 was
found to be stable to strongly acidic conditions and was hydrolyzed
to 70 using a mixture of strong acids with good yields.
Synthesis of compound 71 began with chloride compound 78. Nucleophilic substitution with 4-chloro-N-methylaniline afforded pyrone 87. Dehydration, as previously
described, yielded 88 in moderate to low yields. Hydrolysis
in the presence of strong acid afforded 71.

Credille C.V., Chen Y, & Cohen S.M. (2016). Fragment-Based Identification of Influenza Endonuclease Inhibitors. Journal of Medicinal Chemistry, 59(13), 6444-6454.

Publication 2016

Synthesis and Characterization of 2-Selenobenzoic Acid Amide

Cited 3 times

To a suspension of 7 [52 (link)] (175 mg, 0.44 mmol) in dry toluene (3 mL), thionyl chloride (0.2 mL, 2.82 mmol) was added. The resulting mixture was refluxed until no gas evolution was observable and a clear solution was formed. The unreacted thionyl chloride was evaporated in vacuo and the residue was washed with dry toluene (three times, 2 mL each). The brown oil was solubilized in dry THF (8 mL) and poured into a 3 neck round bottom flask then pure ammonia was added until a precipitate was formed. The suspension was allowed to react at room temperature for 12 h. The solid was filtrated and the filtrate was evaporated in vacuo giving a yellow solid which was treated with Et₂O then filtered and recrystallized from EtOH giving the target compound as a white solid (120 mg; 71% yield). Mp = 221–223 °C; ¹H-NMR (DMSO-d₆) δ: 7.40 (t, J = 7.79 Hz, 1H, ArH); 7.60 (t, J = 8.29 Hz, 1H, ArH); 7.80 (dd, J = 0.72 and 7.77 Hz, 1H, ArH); 8.03 (d, J = 8.29 Hz, 1H, ArH); 9.18 (bs, 1H, NH) ppm; ¹³C-NMR (DMSO-d₆) δ: 125.77; 126.39; 127.40; 127.68; 131.70; 141.56; 168.89 ppm. ⁷⁷Se NMR (DMSO-d₆) δ: 796.71 ppm. HRMS calculated for [C₇H₆NOSe⁺] = 199.9615 found = 199.9621

Krasowska D., Iraci N., Santi C., Drabowicz J., Cieslak M., Kaźmierczak-Barańska J., Palomba M., Królewska-Golińska K., Magiera J, & Sancineto L. (2019). Diselenides and Benzisoselenazolones as Antiproliferative Agents and Glutathione-S-Transferase Inhibitors. Molecules, 24(16), 2914.

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Publication 2019

1H NMR Ammonia Biological Evolution Carbon-13 Magnetic Resonance Spectroscopy Ethanol Neck Sulfoxide, Dimethyl thionyl chloride Toluene

Most recents protocols related to «Thionyl chloride»

Synthesis of Acid Chloride Reagents

It was necessary to obtain some acid chloride reagents. For this purpose, these compounds were synthesized by treatment of the corresponding carboxylic acid with an excess of thionyl chloride (20 mL) at reflux for 2 h. The novel acid chloride was isolated by the rotary evaporation of the thionyl chloride under vacuum, and the excess of thionyl chloride was removed by adding three fractions of methylene chloride (3 × 50 mL). The resulting acid chlorides were used without further purification.

Angulo-Elizari E., Raza A., Encío I., Sharma A.K., Sanmartín C, & Plano D. (2024). Seleno-Warfare against Cancer: Decoding Antitumor Activity of Novel Acylselenoureas and Se-Acylisoselenoureas. Pharmaceutics, 16(2), 272.

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Publication 2024

Synthesis of Acyl Chlorides

A solution of 3,5-dinitrobenzoic acid or benzoic acid in thionyl chloride (2 mL per mmol of acid) was refluxed for 12 h, leading to the formation of the respective acyl chloride. The excess thionyl chloride was removed by low pressure evaporation. The product was used without further purification.

Delgado T., Pais J.P., Pires D., Estrada F.G., Guedes R.C., Anes E, & Constantino L. (2024). Development of New Drugs to Treat Tuberculosis Based on the Dinitrobenzamide Scaffold. Pharmaceuticals, 17(5), 559.

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Publication 2024

Synthesis of Carboxylic Acid Derivatives

A mixture of corresponding carboxylic acids 23 and 27 and thionyl chloride in absolute toluene was refluxed for 22 h.
Toluene and excess thionyl chloride were removed under reduced pressure. The crude product was washed 3 times with absolute toluene to obtain the powdered product.

Perin N., Gulin M., Kos M., Persoons L., Daelemans D., Fabijanić I., Stojković M.R, & Hranjec M. (2024). Synthesis and Biological Evaluation of Novel Amino and Amido Substituted Pentacyclic Benzimidazole Derivatives as Antiproliferative Agents. International Journal of Molecular Sciences, 25(4), 2288.

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Publication 2024

Synthesis of Carboxylic Acid Derivatives

A mixture of carboxylic acid 27, thionyl chloride, and DMF in absolute toluene was stirred at room temperature for 10 min; after that, the appropriate amine was added and heated at reflux. Toluene and excess thionyl chloride were removed under reduced pressure. The crude product was washed 3 times with toluene to obtain powdered product. The resulting product was separated by column chromatography on SiO₂ using dichloromethane/methanol as eluent.

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Publication 2024

Synthesis of Nicotinoyl Isothiocyanate

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Publication 2024

Top products related to «Thionyl chloride»

Thionyl chloride by Merck Group

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Thionyl chloride is a colorless, fuming liquid chemical compound. It is commonly used as a reagent in organic synthesis reactions. The primary function of thionyl chloride is to convert alcohols, carboxylic acids, and other compounds into more reactive derivatives such as acyl chlorides and sulfinyl chlorides.

Triethylamine by Merck Group

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Triethylamine is a clear, colorless liquid used as a laboratory reagent. It is a tertiary amine with the chemical formula (CH3CH2)3N. Triethylamine serves as a base and is commonly employed in organic synthesis reactions.

Thionyl chloride by Thermo Fisher Scientific

Sourced in Belgium, United States

Thionyl chloride (SOCl2) is a colorless, fuming liquid chemical compound. It is a common reagent used in organic synthesis, typically as a chlorinating agent or for the preparation of acid chlorides. Thionyl chloride has a pungent odor and is highly reactive with water.

Hydrochloric acid (hcl) by Merck Group

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Hydrochloric acid is a commonly used laboratory reagent. It is a clear, colorless, and highly corrosive liquid with a pungent odor. Hydrochloric acid is an aqueous solution of hydrogen chloride gas.

Dimethylformamide by Merck Group

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Dimethylformamide is a colorless, hygroscopic, and highly polar organic solvent. It is commonly used as a laboratory reagent and in various industrial applications.

Sodium hydroxide (naoh) by Merck Group

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Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.

Dimethyl sulfoxide (dmso) by Merck Group

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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.

Dichloromethane by Merck Group

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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.

Acetonitrile by Merck Group

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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.

Methanol by Merck Group

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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.

What are the common applications of Thionyl chloride (SOCl2)?

Thionyl chloride (SOCl2) is a versatile reagent with numerous applications in organic synthesis. It is commonly used for acylation, chlorination, and sulfonation reactions. Thionyl chloride is particularly useful for the conversion of alcohols, carboxylic acids, and other functionalities into their corresponding chloro derivatives. It also finds applications in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.

What are some important safety considerations when handling Thionyl chloride?

Thionyl chloride is a highly reactive and corrosive substance, so researchers must exercise caution when working with it. It is essential to follow appropriate safety protocols, such as using personal protective equipment (PPE), working in a fume hood, and properly disposing of waste materials. Exposure to Thionyl chloride can be hazardous, so it is crucial to minimize the risk of accidental contact or inhalation.

Are there different variations or types of Thionyl chloride available?

Yes, there are several variations of Thionyl chloride available, including high-purity grades and various solvent mixtures. The choice of Thionyl chloride type may depend on the specific requirements of your research or application. It's important to carefully select the appropriate Thionyl chloride product to ensure the reproducibility and reliability of your experiments.

How can PubCompare.ai help in the optimal use of Thionyl chloride?

PubCompare.ai's AI-powered research optimization tools can greatly assist in the effective use of Thionyl chloride. The platform allows you to efficiently screen protocol literature, leveraging AI to identify critical insights. By comparing the effectiveness of different Thionyl chloride protocols, PubCompare.ai can help you choose the best option for your specific research goals, ensuring reproducibility and accuracy. This can save you time and effort, while also improving the quality of your experiments.

Are there any common usage challenges associated with Thionyl chloride?

Yes, there are some common usage challenges with Thionyl chlorise. Due to its high reactivity and corrosiveness, it can be challenging to work with Thionyl chloride in a consistent and reproducible manner. Factors such as temperature, reaction time, and the presence of other reagents can all impact the effectiveness of Thionyl chloride in your experiments. Careful optimization and attention to detail are crucial when using this versatile yet demanding reagent.

More about "Thionyl chloride"

Thionyl chloride (SOCl2) is a versatile and highly reactive organosulfur compound with numerous applications in organic synthesis.
It serves as a valuable reagent for a variety of chemical transformations, including acylation, chlorination, and sulfonation reactions.
Thionyl chloride is frequently used to convert alcohols, carboxylic acids, and other functionalities into their corresponding chloro derivatives, making it a crucial tool for organic chemists.
In addition to its synthetic utility, thionyl chloride is also employed in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Its ability to introduce chloro groups and activate various functional groups has made it an indispensable reagent in the development of a wide range of products.
Closely related to thionyl chloride are other reagents like triethylamine, hydrochloric acid, dimethylformamide, sodium hydroxide, DMSO, dichloromethane, acetonitrile, and methanol.
These compounds often play complementary roles in organic synthesis, either as solvents, bases, or auxiliary reagents, and can be used in conjunction with thionyl chloride to achieve specific desired transformations.
When working with thionyl chloride, researchers must exercise caution as it is a corrosive and potentially hazardous substance.
Proper safety protocols, such as the use of personal protective equipment and well-ventilated workspaces, are essential to ensure the reproducibility and reliability of experiments involving this reagent.
By following best practices and utilizing the latest advancements in research optimization tools, such as those offered by PubCompare.ai, scientists can unlock the full potential of thionyl chloride and elevate the quality and efficiency of their organic synthesis research.