6320-03-2

Basic information

• Product Name: 2-CHLOROTHIOPHENOL
• Synonyms: O-CHLOROTHIOPHENOL;2-CHLOROBENZENETHIOL;2-CHLOROTHIOPHENOL;1-CHLORO-2-MERCAPTOBENZENE;2-chloro-benzenethio;Benzenethiol, o-chloro-;Benzenethiol,2-chloro-;o-Chlorobenzenethiol
• CAS NO: 6320-03-2
• Molecular Formula: C₆H₅ClS
• Molecular Weight: 144.62
• EINECS: 228-667-5
• Product Categories: Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles
• Mol File: 6320-03-2.mol

Chemical Properties

• Boiling Point: 205-206 °C260 mm Hg(lit.)
• Flash Point: 191 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.275 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.344mmHg at 25°C
• Refractive Index: n20/D 1.6029(lit.)
• PKA: 5.90±0.43(Predicted)
• Water Solubility: 2.4g/L at 20℃
• Sensitive: Stench/Lachrymatory
• BRN: 1209665
• CAS DataBase Reference: 2-CHLOROTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROTHIOPHENOL(6320-03-2)
• EPA Substance Registry System: 2-CHLOROTHIOPHENOL(6320-03-2)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37-20/21/22
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 9-13-23-19
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6320-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorothiophenol is used as a synthetic intermediate for the production of bis(2-chlorophenyl) analog of aromatic disulfide, which has potential applications in the development of pharmaceuticals. Its unique chemical properties allow for the creation of novel compounds with potential therapeutic benefits.
Used in Chemical Synthesis:
As a synthetic intermediate, 2-Chlorothiophenol is used in the chemical synthesis of various organic compounds. Its ability to undergo Smile rearrangement with chloroacetyl chloride and primary aliphatic amines makes it a valuable component in the development of new materials and products across different industries.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H5ClS/c7-5-3-1-2-4-6(5)8/h1-4,8H/p-1

Upstream product

• 95-51-2 o-chloroaniline 
• 95-50-1 1,2-dichloro-benzene 
• 75-08-1 ethanethiol 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 18619-18-6 (2-chloro-phenylsulfanyl)-acetic acid 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 7647-01-0 hydrogenchloride 
• 89-90-7 2-chlorobenzenediazonium chloride 
• 140-89-6 potassium ethyl xanthogenate 
• 694-80-4 2-bromo-1-chlorobenzene 

Downstream Products

• 105974-13-8 trithiocarbonic acid bis-(2-chloro-phenyl ester) 
• 101724-25-8 3t-(2-chloro-phenylsulfanyl)-acrylic acid 
• 99419-77-9 2-(2-chloro-phenylsulfanyl)-5-nitro-benzoic acid 
• 18619-18-6 (2-chloro-phenylsulfanyl)-acetic acid 
• 17733-22-1 2-chlorothioanisole 
• 14575-10-1 o-chlorobenzenesulfenyl chloride 
• 31121-19-4 bis(2-chlorobenzene)disulfide 
• 105972-85-8 bis((2-chlorophenyl)thio)methane 
• 99585-16-7 3-[(2-chlorophenyl)thio]propanoic acid 
• 101421-29-8 (2-chloro-phenyl)-trichloromethyl disulfide 
• 33253-01-9 (2-chloro-phenyl)-(2-nitro-phenyl)-sulfane 
• 29270-06-2 1,2-bis-(2-chloro-phenylsulfanyl)-ethane 
• 63918-04-7 diethyl-[2-(2-chloro-phenylsulfanyl)-ethyl]-amine 
• 33668-01-8 (2-chloro-phenyl)-(2,4-dinitro-phenyl)-sulfide 

Relevant articles and documents

The aromatic thiol compound (by machine translation)

[A] at a high rate, and, high purity aromatic thiol compound method. [Solution] the presence of metal sulfide, with a compound represented by formula (1), by a vapor phase reaction of hydrogen sulfide, (2) an aromatic thiol compound represented by the formula manufacturing method. (R are each independently, C1 a-4 alkyl group, a hydroxyl group, amino group, cyano group, nitro group, C1 a-2 alkoxy group or a halogen atom; n is an integer of 0 - 5; X is a halogen atom)[Drawing] no (by machine translation)

Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis

Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with σI, σ°R values and the meta-compounds correlate well with F,R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's σI and σ°R and charton's steric parameter v. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Oxidative Cleavage of S-Arylmercaptoacetic Acids by Sodium Perborate: Kinetic and Correlation Study

Kinetics of oxidation of twenty six S-arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium.The product of oxidation is the corresponding thiophenol.The rate data of meta- and para-substituted acids have been correlated with DSP equations.While the para-compounds correlate well with ?I and ?0R values, the meta-compounds correlate well with ?I and ?-R values.The reaction constants are negative and of smaller magnitudes.Further, the ortho-substituted acids show a good correlation with a triparametric equation involving Taft's ?I and ?0R and Charton's steric parameter ν.There is a considerable steric contribution to the total ortho-substituent effect.Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

(Bezimidazol-2-yl)-pyridinium compounds

(Benzimidazol-2-yl)-pyridinium compounds of the formula STR1 wherein A is --SR9, --SO3- or --S--SO3- ; R1 and R3 each is hydrogen or (C1 -C7)-alkyl; R2 is hydrogen, (C1 -C7)-alkyl, (C1 -C7)-alkoxy or a negatively charged oxygen atom; R4 is hydrogen or a negative charge; R5, R6, R7 and R8 each is hydrogen, (C1 -C7)-alkyl, aryl, halogen, cyano, nitro, formyl, (C2 -C7)-alkanoyl, arylcarbonyl, carboxy, carboxy-(C1 -C7)-alkyl, (C1 -C7)-alkoxycarbonyl, aryloxycarbonyl, aryl-(C1 -C7)-alkoxycarbonyl, (C1 -C7)-alkoxycarbonyl-(C1 -C7)-alkyl, carbamoyl, mono- or di-(C1 -C7)-alkylcarbamoyl, pyrrolidinocarbonyl, piperidinocarbonyl, carbamoyl-(C1 -C7)-alkyl, mono- or di-(C1 -C7)-alkylcarbamoyl-(C1 -C7)-alkyl, pyrrolidinocarbonyl-(C1 -C7)-alkyl, piperdinocarbonyl-(C1 -C7)-alkyl, hydroxy, (C1 -C7)-alkoxy, (C2 -C7)-alkanoloxy, aryloxy, arylcarbonyloxy, (C1 -C7)-alkoxycarbonyloxy, aryl-(C1 -C7)-alkoxycarbonyloxy, aryloxycarbonyloxy, carbamoyloxy, mono- or di-(C1 -C7)-alkylcarbamoyloxy, pyrrolidinocarbonyloxy, piperidinocarbonyloxy, hydroxy-(C1 -C7)-alkyl, trifluoromethyl, di-(C1 -C7)-alkoxymethyl or (C2 -C3)-alkylenedioxymethyl or two of these substituents which are adjacent jointly and together with the carbon atoms to which they are attached are a 5-, 6- or 7-membered ring; and R9 is (C1 -C20)-alkyl, (C3 -C7)-cycloalkyl, (C3 -C7)-alkenylalkyl, (C3 -C7)-alkynylalkyl, substituted (C3 -C7)- alkenyl-alkyl, aryl, aryl-(C1 -C7)-alkyl, hydroxy- (C2 -C7)-alkyl, (C1 -C7)-alkoxy- (C2 -C7)-alkyl, (C1 -C7)-alkoxycarbonyl- (C1 -C7)-alkyl, carboxy-(C1 -C7)-alkyl, di-(C1 -C7)-alkoxycarbonyl-(C2 -C7)-alkyl, dicarboxy-(C2 -C7)-alkyl, carboxy-(C1 -C7)-alkylcarbamoyl-(C1 -C7)-alkyl, optionally N-substituted amino-(C2 -C7)-alkyl, optionally N-substituted amino-carboxy-(C2 -C7)-alkyl, optionally N-substituted amino-(C1 -C7)-alkoxycarbonyl-(C2 -C7)-alkyl, heteroaryl, heteroaryl-(C1 -C7)-alkyl or a residue derived from a cysteine-containing oligopeptide by elimination of the SH group; provided that when there is a net single positive charge there is an external anion, or a pharmaceutically acceptable acid addition salt thereof.

HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE

Alkanethiols react effectively with chlorobenzene, its derivatives, 1-chloronaphthalene, and 2-chlorothiophene at 600-660 deg C with the preferential formation of the corresponding aromatic or heteroatomic thiols.Ethanethiol is most reactive.When it is used instead of hydrogen sulfide in reactions with chlorobenzene or its 4-substituted derivatives, the yield of the aromatic thiols, from which the phenylthiyl radicals are generated with greater difficulty, increases more sharply than the yield of the thiophenols, which generate the more stable 4-XC6H4S radicals.The side products of the reactions are the corresponding diaryl sulfides, thiophene, benzothiophene, and toluene.

SYNTHESIS AND CONFIGURATIONAL STUDIES OF ARYL CYCLOPROPYL SULFONES

The cycloaddition of arylthiocarbenes to styrene gave stereospecifically cis-1-(arylthio)-2-phenylcyclopropanes, which were subsequently oxidized to the corresponding sulfones.The cyclopropanation of α,β-unsaturated sulfones with dimethylsulfonium methylide yielded stereoselectively trans-1-(arylsulfonyl)-2-arylcyclopropanes.The configurational assignments of these compounds have been arrived at on the basis of IR and PMR spectral data.Chemical shifts for ring protons and other substituents reveal that all the substituents tend to cause protons cis to them to appear at higher fields than those trans to them.This has been used as a criterion to distinguish between cis and trans aryl cyclopropyl sulfones.

Antimicrobial composition and method containing N-(3,5-dihalophenyl)-imide compounds

Novel N-(3,5-dihalophenyl)imide compounds, which exhibit a strong antimicrobial activity against microorganisms including phytopathogenic fungi, parasites of industrial products and pathogenic microorganisms, represented by the formula, STR1 wherein X and X' each represent halogens and A represents a substituted ethylene such as chloroethylene, C1 - C4 alkylthioethylene, C1 - C2 alkyl-ethylene or 1,2-di-C1 - C2 -alkyl-ethylene, a cyclopropylene such as 1,3-dimethylcyclopropylene, trimethylene, a cyclohexylene-1,2-, cyclohexenylene-1,2-, cyclohexadienylene-1,2- or o-phenylene. The N-(3,5-dihalophenyl)imide compounds can be obtained by any of methods which produce imide compounds or reaction of an N-(3,5-dihalophenyl)maleimide compound with a mercaptan, a hydrogen halide, phosphorus chloride or thionylchloride.