3335-22-6

Basic information

• Product Name: Benzenecarbothioyl chloride
• Synonyms: Thiobenzoyl chloride;Benzoyl chloride, thio- (6CI,7CI,8CI)
• CAS NO: 3335-22-6
• Molecular Formula: C₇H₅ClS
• Molecular Weight: 156.636
• Mol File: 3335-22-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 218.95 °C at 760 mmHg
• Flash Point: 86.219 °C
• Density: 1.266 g/cm³
• CAS DataBase Reference: Benzenecarbothioyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarbothioyl chloride(3335-22-6)
• EPA Substance Registry System: Benzenecarbothioyl chloride(3335-22-6)

Safety Data

• Hazardous Substances Data: 3335-22-6(Hazardous Substances Data)

Usage

General Description

Benzenecarbothioyl chloride, also known as benzoyl chloride, is a chemical compound with the formula C7H5C(O)Cl. It is a colorless to pale yellow liquid with a strong, irritating odor. Benzenecarbothioyl chloride is primarily used as a reagent in organic synthesis, particularly in the production of dyes, perfumes, and pharmaceuticals. It is also used in the production of polymers and as a precursor to benzoic acid and benzophenone. The compound is highly reactive and must be handled carefully as it can cause severe burns and irritation to the skin, eyes, and respiratory system. It is classified as a hazardous chemical and should be stored and used in a well-ventilated area with proper protective equipment.

Upstream product

• 121-68-6 dithiobenzoic acid 
• 97346-89-9 bis(thiobenzoyl) trisulfide 
• 19807-41-1 chlorophenylcarbene 
• 7719-09-7 thionyl chloride 
• 60-29-7 diethyl ether 
• 98-91-9 thiobenzoic acid 

Downstream Products

• 103752-80-3 5-phenyl-[1,3,4]thiadiazole-2-carboxylic acid methyl ester 
• 14606-38-3 bis-(α-phenyliminobenzyl) sulfide 
• 34733-85-2 5-phenyl-1,2,3,4-thiatriazole 
• 636-04-4 N-Phenylbenzothioamide 
• 936-63-0 S-ethyl dithiobenzoate 
• 861373-81-1 chloro-triphenyl-thiirane 
• 1456-21-9 diphenyl-[1,3,4]thiadiazole 
• 1137-44-6 4-methylthiobenzophenone 
• 114676-37-8 2,4-Bis(methylthio)-6-phenyl-1,3,5-thiadiazinium-hexachloroantimonat(V) 
• 126912-26-3 1,2-dimethyl-1,2-di(thiobenzoyl)hydrazine 
• 1666-13-3 diphenyl diselenide 
• 120449-41-4 Se-phenyl benzene-carboselenothioate 
• 2168-78-7 methyl dithiobenzoate 
• 23450-23-9 p-Thionbenzoyloxydiphenylmethan 

Relevant articles and documents

A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride

Herein we report the mild and rapid fluorodesulfurization of thionoesters using only silver(I) fluoride. This reaction demonstrates excellent functional group tolerance and complements existing strategies for difluoroalkyl ether synthesis, which rely on t

Laser flash photolysis studies of oxygen and sulfur atom transfer reactions from oxiranes and thiiranes to singlet carbenes

Laser flash photolysis (UV-LFP) studies of benzylchlorodiazirine (1a), phenylchlorodiazirine (1b), phenylmethoxydiazirine (1c), 2,2-dimethoxy-5,5- dimethyl-Δ3-1,3,4-oxadiazoline (6a), 3,4-diaza-2,2-dimethoxy 1- oxa[4.3]spirooct-3-ene (6b), 5',5'-dimethoxyspiro[adamantane]-2,2 -[Δ3- 1,3,4-oxadiazoline] (6c), and diazofluorene (DAF) in the presence of oxiranes and thiiranes are reported. These compounds, upon irradiation, afford benzylchlorocarbene (2a), phenylchlorocarbene (2b), methoxyphenylcarbene (2c), dimethylcarbene (8a), cyclobutylidene (8b), adamantylidene (8c), and fluorenylidene (FL), respectively. Absolute rate constants for the transfer of oxygen and sulfur atoms to these carbenes have been determined in both acetonitrile and cyclohexane solvents. These carbenes abstract oxygen and sulfur atoms with bimolecular rate constants ranging from 104 to 1010 M- 1 s-1 at 22 °C. Ylides from attack of carbenes onto heteroatom donors were not observed for any of the heteroatom transfer reactions. It was found that the magnitudes of the rate constants for heteroatom transfer are dependent on the philicity of the carbene intermediate, and trends in the kinetic data suggest that oxygen and sulfur atom transfers occur by concerted mechanisms through ylide-like transition states. The reactions of dimethoxycarbene (14) with cyclohexene oxide and propylene sulfide have been studied by the thermolysis of 6a, in benzene, at 110 °C. It was found that dimethoxycarbene also abstracts oxygen and sulfur atoms, albeit in low yields. It is concluded that, for singlet carbenes, carbene electrophiiicity is important in these heteroatom transfer processes.