2757-23-5

Basic information

• Product Name: CHLOROCARBONYLSULFENYL CHLORIDE
• Synonyms: CHLOROFORMYLSULFENYL CHLORIDE;CHLOROCARBONYLSULFENYL CHLORIDE;CHLOROCARBONYLSULPHENYL CHLORIDE;CHLOROTHIOFORMYL CHLORIDE;CTFC;Chloroformylsulphenyl chloride;Chlorocarbonylsulfenylchloride,97%;(Chlorothio)formyl chloride, Chloroformylsulfenyl chloride
• CAS NO: 2757-23-5
• Molecular Formula: CCl₂OS
• Molecular Weight: 130.98
• EINECS: 220-415-2
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 2757-23-5.mol

Chemical Properties

• Boiling Point: 98 °C(lit.)
• Flash Point: 98-101°C
• Appearance: Yellow/Liquid, Fuming In Moist Air
• Density: 1.552 g/mL at 25 °C(lit.)
• Vapor Pressure: 40.7mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 506318
• CAS DataBase Reference: CHLOROCARBONYLSULFENYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROCARBONYLSULFENYL CHLORIDE(2757-23-5)
• EPA Substance Registry System: CHLOROCARBONYLSULFENYL CHLORIDE(2757-23-5)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 9-13-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2757-23-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CHLOROCARBONYLSULFENYL CHLORIDE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its application is crucial in the production of commercially important N,N-dialkylcarbamoyl chlorides, which are essential in the development of drugs with diverse therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, CHLOROCARBONYLSULFENYL CHLORIDE serves as a valuable reagent for the preparation of a variety of complex organic molecules. It is used in the synthesis of 5-(1,2,3,4-tetra-O-acetyl-alpha-D-xylopyranos-5S-C-yl)-1,3,4-oxathiazol-2-one, fluorinated oxathialones, polyfluoroalkylchlorothioformates, chlorocarbonylpolyfluoroalkylsulfenate esters, and chlorocarbonylhexafluoroisopropylidenimino sulfenate. These compounds find applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Materials Science:
CHLOROCARBONYLSULFENYL CHLORIDE is also utilized in the development of novel materials with specific properties. For instance, it is employed in the synthesis of 5-tri-fluoromethyl-2-oxo-1,3,4-oxathiazole, which can be used to create advanced materials with unique characteristics for various applications, such as in electronics, coatings, and adhesives.

InChI:InChI=1/CCl2OS/c2-1(4)5-3

Upstream product

• 594-42-3 chlorothio-trichloro-methane 
• 87463-08-9 (methoxydichloromethyl)sulfenyl chloride 
• 87463-09-0 (ethoxydichloromethyl)sulfenyl chloride 
• 85963-74-2 2,2,4,4-tetrachlor-1,3-dithietan-1,3-dioxids 
• 463-58-1 carbon oxide sulfide 
• 7782-50-5 chlorine 

Downstream Products

• 40235-78-7 4-methyl-2-thiazolone-5-carboxylic acid ethyl ester 
• 5852-49-3 5-phenyl-1,3,4-oxathiazol-2-one 
• 17452-74-3 5-Methyl-1,3,4-oxathiazole-2-one 
• 26555-40-8 metgoxycarbonylsulfenyl chloride 
• 81485-47-4 Cyclohexyl-chlorcarbonyl-disulfid 
• 23589-68-6 HT₁₁₁₈ 
• 52059-65-1 5-(4-fluorophenyl)-1,3,4-oxathiazol-2-one 
• 52059-64-0 HT₁₀₇₁ 
• 23589-73-3 5-(3-chlorophenyl)-1,3,4-oxathiazol-2-one 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 
• 67048-91-3 5-(2,6-dichloro-phenyl)-[1,3,4]oxathiazol-2-one 
• 57459-15-1 HT₁₀₈₆ 
• 67048-87-7 4-(2-oxo-[1,3,4]oxathiazol-5-yl)-benzonitrile 
• 52059-69-5 5-(4-iodo-phenyl)-[1,3,4]oxathiazol-2-one 

Relevant articles and documents

Improved method for the preparation of 1,1-dimethyl-3-arylureas using chlorocarbonylsulfenyl chloride

A convenient procedure for preparing some arylureas having herbicidal properties is reported. The method has two steps: (1) reaction of arylamine with chlorocarbonylsulfenyl chloride in the presence of nonpolar solvent to produce aryl carbonylsulfenyl chloride and (2) reaction with dimethylamine in a two-phase reaction catalysed by phase-transfer catalyst to produce the corresponding aryl ureas. Taylor & Francis Group, LLC.

An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives

A convenient one-pot procedure is reported for preparing N,N-disubstituted carbamoyl chlorides by using chlorocarbonylsulfenyl chloride as a carbonylating agent. It comprises the reaction of secondary amines with chlorocarbonylsulfenyl chloride in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halides. Insertion of the carbonyl group without using phosgene is the novelty of this method.

Photochemical reaction channels of OCS with Cl2, ICI, or IBr isolated together in an argon matrix: Isolation of syn-iodocarbonylsulfenyl bromide

The photolytically induced reactions of a dihalogen XY (= Cl2, ICl, or IBr) with OCS isolated together in an Ar matrix at about 15 K lead to different photoproducts depending on the natures of X and Y. In addition to the known species ClCO, OCCl2, syn-ClC(O)SCl, syn-ClC(O)SSCl, IC(O)Cl, IC(O)Br, and ^n-BrC(O)SBr, syn-iodocarbonylsulfenyl bromide, yyn-IC(O)SBr, has thus been identified for the first time as'a photoproduct of the reactions involving IBr. The first product to be formed in the reactions with Cl 2 or ICI is the C1CO radical which reacts subsequently with halogen or sulfur atoms or other matrix guests to give the corresponding carbonyl dihalide (OCCl2 and IC(O)Cl), syn-ClC(O)SCl or syn-ClC(O)SSCl. The analogous reaction with IBr affords syn-BrC(O)SBr, IC(O)Br, and syn-IC(O)SBr. The changes have been followed, the products characterized experimentally by IR measurements, and the spectra analyzed in the light of the results of appropriate theoretical calculations.

Characterisierung und Photochemie von (Dihalogenmethylen)sulfoxiden, XYC=S=O

Dihalogenomethylene sulfoxides (dihalogenosulfines) 2a-c were generated by flash vacuum pyrolysis of 2,2,4,4-tetrahalogeno-1,3-dithietane 1,3-dioxides 1a-c and trapping the pyrolysis products in argon at 10 K.At room temperature unstable difluorosulfine (2a) and chlorofluorosulfine (2b) were identified by i.r.spectroscopy, and the photochemistry of the sulfines was investigated.Chlorofluorosulfine (2b) exists in two geometrical isomers.Photolysis of 2a leads to fragmentation to give CF2 and SO, photolysis of the chlorine containing sulfines 2b and 2c to rearrangement to give sulfenyl chlorides 6 and 8.This is explained by different migratory tendencies of fluorine and chlorine and the stability of C-F bond.

A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and Related Derivatives of Thiocarbonic Acids

A variety of sulfenyl chlorides have been reacted with a variety of alkoxythiocarbonyl compounds to give adducts which then lose (spontaneously, or upon thermolysis, or in the presence of Lewis acid catalyst) the alkyl chloride to provide an assortment of dithiocarbonyl compounds in good to excellent yields.The preparations of bis(chlorocarbonyl)disulfane (1), ((trichloromethyl)dithio)carbonyl chloride (2), ((alkoxycarbonyl)dithio)carbonyl chlorides (3 and 4), and (((alkylthio)carbonyl)dithio)carbonyl chlorides (5 and 6) by this methodology were optimized; some of the (alkoxydichloromethyl)disulfanyl adducts, e.g., ROCCl2SS(C=O)Cl (10) and ROCCl2SS(C=O)OR'(54), were reasonable stable and could be isolated.All new compounds were characterized by analytical data, 1H and 13C NMR, IR, UV, and mass spectrometry, and high-yield derivatizations with alcohols or N-methylaniline.The reaction with N-methylaniline was also adapted to a rapid, convenient, and precise analytical-scale assay of mixtures of compounds containing acid chloride and/or sulfenyl chloride functionalities.The kinetics, mechanism, and stereochemistry of the dithiocarbonyl synthesis are discussed.

3-Aryl-4-isothiazolecarboxylic acid and 3-aryl-4-isoxazolecarboxylic acid derivatives and their use as herbicides

Carboxylic acid derivatives having the formula STR1 have been found to be effective herbicides. They are especially effective when applied as a pre-emergent herbicide.