5858-18-4

Basic information

• Product Name: 2,5-DICHLOROTHIOPHENOL
• Synonyms: 2,5-DICHLOROTHIOPHENOL;2,5-DICHLOROBENZENETHIOL;2,5-DICHLOROBENZENE-1-THIOL;2,5-dichloro-benzenethio;Thiophenol, 2,5-dichloro-;2,5-Dichlorobenzenthiol;Dichlorobenzenthiol,97%;2,5-Dichlorothiophenol,98%
• CAS NO: 5858-18-4
• Molecular Formula: C₆H₄Cl₂S
• Molecular Weight: 179.07
• EINECS: 227-486-9
• Product Categories: Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 5858-18-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 22-25°C
• Boiling Point: 112-116 °C50 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless to yellow liquid after melting
• Density: 1.3905 (estimate)
• Vapor Pressure: 0.419mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.12±0.48(Predicted)
• Sensitive: Stench
• BRN: 2042866
• CAS DataBase Reference: 2,5-DICHLOROTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLOROTHIOPHENOL(5858-18-4)
• EPA Substance Registry System: 2,5-DICHLOROTHIOPHENOL(5858-18-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT, STENCH
• PackingGroup: III
• Hazardous Substances Data: 5858-18-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid after melting

Uses

2,5-Dichlorobenzenethiol may be used in the synthesis of radiolabeled alkyl aryl ethers and sulphides via phase transfer catalysis and chlorinated biphenyl methylsulfonyl metabolites.

InChI:InChI=1/C6H4Cl2S/c7-4-1-2-5(8)6(9)3-4/h1-3,9H/p-1

Upstream product

• 5402-73-3 2,5-dichlorobenzenesulphonyl chloride 
• 7440-06-4 platinum 
• 95-82-9 2,5 dichloroaniline 
• 120-28-5 2,5-dichlorophenyl-diazonium chloride 
• 89-61-2 2,5-dichloronitrobenzene 
• 106-46-7 para-dichlorobenzene 
• 120-82-1 1,2,4-Trichlorobenzene 

Downstream Products

• 69925-18-4 2,5-dichloro-benzenethiosulfonic acid S-(2,5-dichloro-phenyl ester) 
• 109041-33-0 bis-(2,5-dichloro-phenyl)-trisulfide 
• 5335-80-8 di(2,5-dichlorophenyl)disulfide 
• 54583-12-9 chloromethyl-(2,5-dichloro-phenyl)-sulfide 
• 1762-78-3 2,5-dichlorobenzenesulfenyl chloride 
• 860596-90-3 3,6-dichloro-2-(2,5-dichloro-phenyldisulfanyl)-benzoic acid 
• 6274-27-7 [(2,5-dichlorophenyl)thio]acetic acid 
• 17733-24-3 1,4-Dichlor-2-(methylthio)benzol 
• 860241-12-9 (4-chloro-2-nitro-phenyl)-(2,5-dichloro-phenyl)-sulfide 
• 34650-12-9 <2-Hydroxy-aethyl>-<2,5-dichlor-phenyl>-sulfid 
• 5394-31-0 (2,5-dichloro-phenyl)-(tetra-O-acetyl-1-thio-β-D-glucopyranoside) 
• 20066-63-1 2-Nitro-4-chlor-5-(2',5'-dichlorphenylthio)anilin 
• 199739-73-6 (6R,7R)-7-tert-Butoxycarbonylamino-3-(2,5-dichloro-phenylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

Process for preparing 2,5-dichlorophenylthioglycollic acid

A valuable starting material for the manufacture of tetrachlorothioindigo pigments is 2,5-dichlorophenylthioglycollic acid which is prepared by: (a) diazotizing 2,5-dichloroaniline with aqueous alkali metal nitrite at acidic pH to produce 2,5-dichlorophenyl-diazonium salt, (b) reacting the 2,5-dichlorophenyl-diazonium salt from (a) with thiourea in an aqueous medium at acidic pH in the presence of a catalyst to produce 2,5-dichlorophenyl-isothiuronium salt of the formula STR1 wherein X? is an anion of a mineral acid, (c) hydroloyzing the 2,5-dichlorophenylisothiuronium salt from (b), without intermediate isolation, at alkaline pH to produce 2,5-dichlorothiophenol and (d) condensing the 2,5-dichlorothiophenol with monochloroacetic acid to produce 2,5-dichlorophenylthioglycollic acid.

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.

Cephalosporin displacement reaction

The present invention is directed to a process for the displacement of the acetoxy group of a cephalosporanic acid by a sulfur nucleophile, in an organic solvent and under essentially anhydrous conditions.