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Thionyl chloride

Base Information
  • Chemical Name:Thionyl chloride
  • CAS No.:7719-09-7
  • Deprecated CAS:2505209-14-1
  • Molecular Formula:Cl2OS
  • Molecular Weight:118.971
  • Hs Code.:2812.10
  • European Community (EC) Number:231-748-8,682-671-5
  • ICSC Number:1409
  • UN Number:1836
  • UNII:4A8YJA13N4
  • DSSTox Substance ID:DTXSID3064778
  • Nikkaji Number:J3.752D
  • Wikipedia:Thionyl chloride,Thionyl_chloride
  • Wikidata:Q409171
  • Mol file:7719-09-7.mol
Thionyl chloride

Synonyms:thionyl chloride

Suppliers and Price of Thionyl chloride
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • SynQuest Laboratories
  • Thionyl chloride 98%
  • 500 g
  • $ 370.00
  • SynQuest Laboratories
  • Thionyl chloride 98%
  • 100 g
  • $ 340.00
  • Sigma-Aldrich
  • Thionyl chloride ReagentPlus?, ≥99%
  • 100 mL
  • $ 59.10
  • Sigma-Aldrich
  • Thionyl chloride for synthesis
  • 500 mL
  • $ 74.55
  • Sigma-Aldrich
  • Thionyl chloride ReagentPlus?, ≥99%
  • 5 mL
  • $ 33.90
  • Sigma-Aldrich
  • Thionyl chloride ReagentPlus?, ≥99%
  • 4 x 100 mL
  • $ 182.00
  • Sigma-Aldrich
  • Thionyl chloride ReagentPlus?, ≥99%
  • 1 L
  • $ 171.00
  • Sigma-Aldrich
  • Thionyl chloride for synthesis
  • 1 L
  • $ 126.72
  • Sigma-Aldrich
  • Thionyl chloride ReagentPlus?, ≥99%
  • 500 mL
  • $ 95.70
  • Sigma-Aldrich
  • Thionyl chloride for synthesis
  • 40 kg
  • $ 912.97
Total 3 raw suppliers
Chemical Property of Thionyl chloride
Chemical Property:
  • Appearance/Colour:Colorless to slightly yellow liquid 
  • Vapor Pressure:97 mm Hg ( 20 °C) 
  • Melting Point:-105 °C 
  • Refractive Index:n20/D 1.518(lit.)  
  • Boiling Point:79 °C at 760 mmHg 
  • Flash Point:105°C 
  • PSA:36.28000 
  • Density:1.956 g/cm3 
  • LogP:1.90840 
  • Storage Temp.:Store at RT. 
  • Sensitive.:Moisture Sensitive 
  • Solubility.:Miscible with toluene, chloroform, benzene, carbon tetrachloride 
  • Water Solubility.:REACTS 
  • XLogP3:1.5
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:117.9046912
  • Heavy Atom Count:4
  • Complexity:29
  • Transport DOT Label:Corrosive
Purity/Quality:

99%min *data from raw suppliers

Thionyl chloride 98% *data from reagent suppliers

Safty Information:
  • Pictogram(s): Corrosive
  • Hazard Codes:
  • Statements: 14-20/22-29-35-40-34-20/21/22 
  • Safety Statements: 26-36/37/39-45-28-27 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Toxic Gases & Vapors -> Acid Halides
  • Canonical SMILES:O=S(Cl)Cl
  • Inhalation Risk:A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
  • Effects of Short Term Exposure:The substance is very corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The substance may cause effects on the lungs. This may result in inflammation and blockage of the airways. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
  • Uses Thionyl chloride is an important intermediate of organic chemistry and is mainly used in medicine, pesticides, dyes and industrial organic synthesis industry as chlorinating agent. Consumption structure: the pharmaceutical industry accounted for 25%, pesticide industry accounted for 50%, dyestuff industry accounted for 5% and other industries accounted for 20%. The pesticide industry contributes the major part for consumption of thionyl chloride and is mainly used for the production of inabenfide, valerate, fenvalerate, mosquito-killing dimerthrin, flucythrinate, diflubenzuron, isocarbophos, fenpropathrin, endosulfan, deltamethrin, a (b) group chlorpyrifos, oxazolidinone, quizalofop and warfarin. Because thionyl chloride can have fierce reaction with water, it is able to have reaction with metal chloride hydrated salt for production with anhydrous metal chlorides. MCln ? xH2O + x SOCl2 → MCln + x SO2 + 2x HCl Thionyl chloride was subjected heating reflux with a transition metal oxide and can further generate the corresponding oxychloride of the metal: WO3 + 2SOCl2 → WOCl4 + 2SO2 Thionyl chloride has been widely used for converting alcohol and the carboxylic acid into the corresponding acid chloride and chlorinated hydrocarbons. Compared with other agents (such as phosphorus penta-chloride), thionyl chloride is often the preferred reagents, because both the reaction product of sulfur dioxide and hydrogen chloride are gaseous and is easily to be separated. The excess amount of thionyl chloride can be removed by distillation. RC (= O)-OH + O = SCl2 → RC (= O)-Cl + SO2 + HCl R-OH + O = SCl2 → R-Cl + SO2 + HCl. Sulfoacid can react with thionyl chloride to generate sulfonyl chloride. Sulfinic acid can have reaction with thionyl chloride to generate sulfinyl chloride. Phosphonic acid can have reaction with thionyl chloride to generate phosphine chloride. Thionyl chloride can react with mono-substituted formamide to generate the corresponding isonitriles. Amide can react with thionyl chloride to generate imine acyl chloride. Primary amide, upon co-heating with thionyl chloride, will be further dehydrated to become nitrile. The above information is edited by the lookchem of Dai Xiongfeng. It can be applied to medicine, pesticide and dye industries and mainly used for the production of isocarbophos, sumicidin, propargite tetramisole hydrochloride, indomethacin, and vitamin A, etc. It can be used as the chlorinating agents for organic synthesis such as chlorination of alcoholic hydroxyl group, chlorination of carboxylic acid, chlorination of acid anhydride and the chlorine displacement of organic sulfonic acid or carboxylic acid. It can also be used for making acyl chloride as well as being used for the manufacture of pharmaceutical intermediates such as tetramisole hydrochloride and synthomycin palmitate. It can also be used as a dehydrating agent or solvent. In the manufacture of lithium batteries; in the synthesis of herbicides, surfactants, drugs, vitamins, and dyestuffs. For making acyl chlorides, to replace OH or SH groups with chlorine atoms; reacts with Grignard reagents to form the corresponding sulfoxides. Review of use in organic synthesis: J. S. Pizey, Synthetic Reagents vol. 1 (John Wiley, New York, 1974) pp 321-357. Thionyl chloride (SOCl2) is used as a chlorinating agent in manufacturing organic compounds. It is also used as a solvent in high-energy lithium batteries.
  • Production method It can be produced with the reaction between sulfur trioxide and sulfur dichloride. Chlorosulfonic acid method: first add sulfur powder to the reactor, put through the chlorine gas for reaction to generate sulfur monochloride. Then add a certain amount of chlorine acid and sulfur monochloride to the reactor; put through chlorine gas at below 50 ℃ for reaction; the resulted mixture was further subject to the crude distillation and condensation; further collect the material liquid below 130 ℃ and feed to the distillation pot; in order to make the low-boiling sulfur dichloride be convert to sulfur chloride for further being left in the pot, then you have to add 15% to 20% the amount of the crude product of sulfur and then send for distillation; reflux for 4h until giving normal color; collect the fraction between 75-80 ℃ to obtain the finished product. The reaction equation is: 2ClSO3H + S2C12 + C12 → 2SOC12 + 2SO2 + 2HCl Sulfur dioxide method: take sulfur, liquid chlorine and liquid sulfur dioxide as raw material; apply whole-cycle and liquid circulation method for production of high-purity alumina thionyl chloride with a purity of 99%; this method has advanced technology, high product quality and releases less "three wastes".
  • Physical properties Pale yellow to red fuming liquid; suffocating odor; refractive index 1.517 at 20°C; density 1.631 g/mL at 20°C; freezes at -101°C; boils at 75.6°C; decomposes at 140°C; decomposes in water; soluble in benzene, chloroform, and carbon tetrachloride.
Technology Process of Thionyl chloride

There total 112 articles about Thionyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Refernces

Synthesis and antiviral activity of new acrylamide derivatives containing 1,2,3-thiadiazole as inhibitors of hepatitis B virus replication

10.1016/j.ejmech.2010.01.032

The study focuses on the synthesis and evaluation of a series of new acrylamide derivatives containing 1,2,3-thiadiazole for their potential antiviral activity against hepatitis B virus (HBV) replication. These compounds were designed based on the structure of known anti-HBV agents and synthesized through various chemical reactions. The in vitro anti-HBV activities were assessed by measuring the inhibition of HBV DNA replication, secretion of HBeAg, and HBsAg in 2.2.15 cells. The results showed that several compounds, particularly 9c, demonstrated higher inhibitory activity against HBV DNA replication compared to the positive control lamivudine. Additionally, compound 9d exhibited significant activity against the secretion of HBeAg. The study concludes that these acrylamide derivatives containing 1,2,3-thiadiazole could serve as promising candidates for the development of new anti-HBV drugs.

Design, synthesis, and structure-activity relationships of pyrazolo[3,4-d]pyrimidines: A novel class of potent enterovirus inhibitors

10.1016/j.bmcl.2004.02.092

The study focuses on the design, synthesis, and evaluation of a novel class of pyrazolo[3,4-d]pyrimidines as potent inhibitors of enteroviruses, specifically coxsackieviruses. The researchers synthesized a series of these compounds and tested their antiviral activity using a plaque reduction assay. They discovered that these compounds showed remarkable specificity for human enteroviruses, with some derivatives highly effective at nanomolar concentrations. Structure-activity relationship (SAR) studies indicated that the phenyl group at the N-1 position and the hydrophobic diarylmethyl group at the piperazine significantly influenced the in vitro antienteroviral activity. Notably, compounds with a thiophene substituent, such as 20–24, exhibited high activity against coxsackievirus B3 and moderate activity against enterovirus 71, without apparent cytotoxic effects on RD cell lines. The findings highlight the potential of these compounds as new antiviral agents against enteroviral infections, for which effective treatments are currently lacking.

1-Benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-ones: Mosher-Bt reagents

10.1021/jo070278a

The focuses on the development and application of Mosher-Bt reagents, which are derivatives of 1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-ones. These reagents are designed to determine the enantiomeric excess and absolute configurations of chiral alcohols and amines using NMR spectroscopy, offering a stable and cost-effective alternative to the commonly used, but costly and sensitive, MTPA chlorides. The study involved the synthesis of racemic and enantiomeric versions of Mosher-Bt reagents and their reactions with water-soluble chiral amino acids and di- and tripeptides in an acetonitrile/water mixture. The results demonstrated that these reagents are non-corrosive, stable to moisture and heat, and can be stored at room temperature, making them easier to handle. They also showed high yields in the formation of Mosher's amides and could be used in aqueous conditions. The chemicals used in the process include 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA), 1H-benzotriazole (BtH), thionyl chloride, and various amino acids, di-, and tripeptides. The research concluded that Mosher-Bt reagents are efficient chiral derivatizing agents that can replace sensitive MTPA chlorides, with the added benefits of being more cost-effective and easier to handle.

Studies on pyrrolidinones. Synthesis and reactivity of some N-protected pyroglutamic derivatives

10.1002/jhet.5570320532

The research focuses on the synthesis and reactivity of N-protected pyroglutamic derivatives, specifically pyroglutamoyl chlorides N-protected by a methoxycarbonyl or a trifluoroacetyl group. The purpose of this study was to develop an easy and convenient synthesis method for these unstable compounds and to explore their reactivity, with the aim of overcoming stability issues and simplifying the deprotection process. The researchers successfully synthesized N-trifluoroacetyl and N-methoxycarbonyl pyroglutamoyl chlorides and studied their reactions with various reagents, including methanol, thionyl chloride, trifluoroacetic anhydride, and methyl chloroformate. They also investigated the condensation of these derivatives with aromatic amines and their reactions with isopropylidene malonate (Meldrum's acid). The study concluded that the protecting groups could be easily removed without opening the lactam ring, and the reactions were effectively monitored using proton nuclear magnetic resonance (1H NMR). The chemicals used in the process included pyroglutamic acid, trifluoroacetic anhydride, methyl chloroformate, thionyl chloride, and various amines, among others.

Synthesis and cytotoxicity studies of quinoline-3-carbonitrile derivatives

10.1016/j.cclet.2010.03.016

The study focuses on the design, synthesis, and in vitro cytotoxicity evaluation of a series of quinoline-3-carbonitrile derivatives against four cancer cell lines: A549 (lung), HT-29 (colon), MDA-MB-231 (breast), and SMMC-7721 (liver). The research aimed to develop potent and selective anti-tumor agents by replacing the quinazoline scaffold of Gefitinib, an EGFR tyrosine kinase inhibitor, with a quinoline-3-carbonitrile scaffold. The synthesized compounds were tested for their cytotoxic effects using the MTT assay, and the results showed that several of these derivatives exhibited superior selective cytotoxicity against the SMMC-7721 cell line compared to Gefitinib, with compound 11g being the most potent among them. The study also provided preliminary insights into the structure-activity relationships of these compounds, suggesting their potential as anti-cancer agents. Further research on their anti-tumor activities and detailed structure-activity relationships is ongoing.

Synthesis and characterisation of novel N substituted 2-methylimidazo[1,2a] pyridine-3-carboxamides

10.3184/174751911X13026260434797

The study presents the synthesis and characterization of novel N-substituted 2-methylimidazo[1,2a]pyridine-3-carboxamides, which are nitrogen bridge-head heterocycles containing an imidazole[1,2a]pyridine ring. These compounds are significant in pharmaceuticals due to their diverse therapeutic activities, including as inhibitors of UV-induced keratinocytic apoptosis, antiviral agents, inhibitors of gastric H+/K+-ATPase, IRAK-4 inhibitors, HIF-1α prolyl hydroxylase inhibitors, and more. The chemicals used in the study include 2-aminopyridine, various amines for substitution, and reagents such as methyl 2-chloro-3-oxobutanoate, sodium hydroxide, thionyl chloride, and triethylamine. These chemicals served the purpose of synthesizing the target compounds through a series of reactions involving condensation, hydrolysis, and amidation. The synthesized compounds were then characterized using techniques like 1H NMR, MS, IR, and elemental analysis to confirm their structures and properties.

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