1004-00-8

Basic information

• Product Name: 2-AMINO-4-CHLOROTHIOPHENOL
• Synonyms: 2-AMINO-4-CHLOROBENZENETHIOL;2-AMINO-4-CHLOROTHIOPHENOL;4-Chloro-2-Aminothio-Phenol;2-amino-4-chloro thoiphenol;2-Amino-4-chlorothiophenol 96%;2-AMINO-4-CHLORO THIOPHENOL 97.0%MIN;5-Chloro-2-mercaptoaniline;4-Chloro-2-aminobenzenethiol
• CAS NO: 1004-00-8
• Molecular Formula: C₆H₆ClNS
• Molecular Weight: 159.64
• Product Categories: Sulphur Derivatives;Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 1004-00-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 56-61 °C(lit.)
• Boiling Point: 281.2 °C at 760 mmHg
• Flash Point: 123.9 °C
• Appearance: /
• Density: 1.372 g/cm³
• Vapor Pressure: 0.00361mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 7.35±0.11(Predicted)
• Water Solubility: Practically insoluble in water
• Sensitive: Stench
• CAS DataBase Reference: 2-AMINO-4-CHLOROTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-CHLOROTHIOPHENOL(1004-00-8)
• EPA Substance Registry System: 2-AMINO-4-CHLOROTHIOPHENOL(1004-00-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1004-00-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystalline

Uses

2-Amino-4-chlorobenzenethiol may be used in the synthesis of:2,3-dihydro-1,5-benzothiazepin-4-(5H)-ones8-chloro-1-azaphenothiazine5-chloro-2-(4-methoxyphenyl)-2,3-dihydro-1,3,2-benzothiazaphosphole 2-sulfide

General Description

2-Amino-4-chlorobenzenethiol reacts with aromatic aldehydes and cyclohexanecarboxaldehyde to afford the corresponding thiazole and thiazoline derivatives. It undergoes oxidation in the presence of 1-n-butyl-3-methylimidazolium methylselenite, [bmim][SeO2(OCH3)] to form the corresponding symmetrical disulfide.

InChI:InChI=1/C6H6ClNS/c7-4-1-2-6(9)5(8)3-4/h1-3,9H,8H2

Upstream product

• 2050-66-0 bis(2-nitro-4-chlorophenyl)disulfide 
• 64-19-7 acetic acid 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 36776-27-9 4-chloro-2-nitro-thiophenol 
• 106-48-9 4-chloro-phenol 
• 89-64-5 p-chloro-o-nitrophenol 
• 5331-91-9 5-chloro-2-mercaptobenzothiazole 
• 20358-00-3 2-amino-5-chlorobenzothiazole 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 7732-18-5 water 
• 89-61-2 2,5-dichloronitrobenzene 

Downstream Products

• 107611-11-0 5-chloro-2-ethylbenzo[d]thiazole 
• 105837-46-5 5-chloro-2-(2-nitro-phenylsulfanyl)-aniline 
• 104115-85-7 5-chloro-2-(5-chloro-2-nitro-phenylsulfanyl)-aniline 
• 101094-79-5 6-chloro-3-phenyl-2H-1,4-benzothiazine 
• 104115-86-8 5-chloro-2-(3-chloro-2-nitro-phenylsulfanyl)-aniline 
• 109503-65-3 5,5'-dichloro-2,2'-(2-nitro-m-phenylenedimercapto)-di-aniline 
• 29241-15-4 5-chlorobenzothiadiazole 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 36868-69-6 (2-amino-4-chloro-phenyl)-(tetra-O-acetyl-1-thio-β-D-glucopyranoside) 
• 75620-23-4 7-chloro-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 92165-16-7 <2-Amino-4-chlor-phenylmercapto>-essigsaeure-anilid 
• 92106-50-8 <2-Amino-4-chlor-phenylmercapto>-essigsaeure-<2,4-dichloranilid> 
• 30302-03-5 3-(2-Amino-4-chloro-phenylsulfanyl)-2-hydroxy-3-p-tolyl-propionic acid ethyl ester 
• 875895-73-1 methyl 2-(((2-amino-4-chlorophenyl)thio)methyl)benzoate 

Relevant articles and documents

Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities

A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.

Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones

A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

Catalytic Enantioselective Synthesis of Protecting-Group-Free 1,5-Benzothiazepines

A one-pot enantioselective route to N-unprotected 2,3-dihydro-1,5-benzothiazepinones, by an organocatalyzed sulfa-Michael reaction of readily available α,β-unsaturated N-acyl pyrazoles with 2-aminothiophenols followed by silica-gel-catalyzed lactamization