5331-91-9

Basic information

• Product Name: 5-Chloro-2-mercaptobenzothiazole
• Synonyms: 5-Chloro-2-mercaptobenzothiazine;5-Chloro-2-benzothiazolethiol, CMBT;2(3H)-Benzothiazolethione, 5-chloro-;5-Chloro-3H-1,3-benzothiazole-2-thione;Benzothiazole, 5-chloro-2-mercapto;5-Chloro-2(3H)-benzothiazolethione;5-Chloro-2-mercaptobenzothiazole,90%;5-Chloro-2-mercaptobenzothiazole,98%
• CAS NO: 5331-91-9
• Molecular Formula: C₇H₄ClNS₂
• Molecular Weight: 201.7
• EINECS: 226-235-0
• Product Categories: BENZOTHIAZOLE;Oxazole&Isoxazole
• Mol File: 5331-91-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 198-200 °C(lit.)
• Boiling Point: 333.2 °C at 760 mmHg
• Flash Point: 155.3 °C
• Appearance: Light yellow to yellow-green granular powder
• Density: 1.4472 (rough estimate)
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• PKA: 8.88±0.20(Predicted)
• CAS DataBase Reference: 5-Chloro-2-mercaptobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-mercaptobenzothiazole(5331-91-9)
• EPA Substance Registry System: 5-Chloro-2-mercaptobenzothiazole(5331-91-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-37/38-36
• Safety Statements: 26-37-36-24/25
• WGK Germany: 3
• RTECS: DL6490000
• Hazardous Substances Data: 5331-91-9(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW TO YELLOW-GREEN GRANULAR POWDER

Uses

5-Chloro-2-mercaptobenzothiazole (CMBZT) has been used in the analysis of lipopolysaccharide by negative-ion matrix-assisted laser desorption ionization-time of flight mass spectrometry. It has been used in the synthesis of the new mixed ligand silver(I) chloride complex with the heterocyclic thioamide CMBZT and tri(p-tolyl)phosphine. Found to be more sensitive than DHB for analysis of high mannose N-linked glycans. Used in analysis of peptidoglycan muropeptides.

General Description

5-Chloro-2-mercaptobenzothiazole(CMBZT) reacts with iodine in a molar ratio of 1:1 to form charge-transfer complex (CMBZT)I2.

InChI:InChI=1/C7H4ClNS2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

Upstream product

• 95-82-9 2,5 dichloroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 2786-51-8 5-chlorobenzo[d]thiazole 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 128-04-1 sodium dimethyldithiocarbamate 
• 75-15-0 carbon disulfide 
• 29124-55-8 2-amino-4-chlorophenyl disulfide 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 6828-35-9 5-chloro-2-iodoaniline 
• 103-72-0 phenyl isothiocyanate 
• 89-61-2 2,5-dichloronitrobenzene 
• 137-26-8 Thiram 

Downstream Products

• 108954-12-7 5-chloro-benzothiazole-2-sulfenic acid cyclohexylamide 
• 23002-94-0 3-anilinomethyl-5-chloro-3H-benzothiazole-2-thione 
• 2786-51-8 5-chlorobenzo[d]thiazole 
• 2941-48-2 2,5-Dichloro-benzothiazole 
• 20600-44-6 5-chloro-1,3-benzothiazol-2(3H)-one 
• 35412-18-1 5-chloro-N-phenylbenzo[d]thiazol-2-amine 
• 108923-25-7 (5-chloro-benzothiazol-2-yl)-nitroso-phenyl-amine 
• 85592-32-1 α-(5-chlorobenzothiazol-2-ylthio)-α-(p-chlorophenyl)acetic acid 
• 20174-72-5 (5-chloro-1,3-benzothiazol-2-yl)hydrazine 

Relevant articles and documents

Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

Limited therapeutic options are available for the treatment of human schistosomiasis caused by the parasitic Schistosoma flatworm. The B cell lymphoma-2 (BCL-2)-regulated apoptotic cell death pathway in schistosomes was recently characterized and shown to share similarities with the intrinsic apoptosis pathway in humans. Here, we exploit structural differences in the human and schistosome BCL-2 (sBCL-2) pro-survival proteins toward a novel treatment strategy for schistosomiasis. The benzothiazole hydrazone scaffold previously employed to target human BCL-XL was repurposed as a starting point to target sBCL-2. We utilized X-ray structural data to inform optimization and then applied a scaffold-hop strategy to identify the 5-carboxamide thiazole hydrazone scaffold (43) with potent sBCL-2 activity (IC50 30 nM). Human BCL-XL potency (IC50 13 nM) was inadvertently preserved during the optimization process. The lead analogues from this study exhibit on-target activity in model fibroblast cell lines dependent on either sBCL-2 or human BCL-XL for survival. Further optimization of the thiazole hydrazone class is required to exhibit activity in schistosomes and enhance the potential of this strategy for treating schistosomiasis.

A Highly Efficient Synthesis of 2-Benzimidazolthiones and Their Congeners under Mild Conditions

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AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.