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

Description

5-Chloro-2-mercaptobenzothiazole (CMBZT) is a light yellow to yellow-green granular powder that is known for its ability to form a charge-transfer complex with iodine in a 1:1 molar ratio. 5-Chloro-2-mercaptobenzothiazole has found various applications in different industries, particularly in the field of chemical analysis and synthesis.

Uses

Used in Chemical Analysis:
5-Chloro-2-mercaptobenzothiazole is used as an analytical reagent for the detection and analysis of lipopolysaccharide through negative-ion matrix-assisted laser desorption ionization-time of flight mass spectrometry. It is also utilized in the analysis of high mannose N-linked glycans, where it has been found to be more sensitive than DHB (2,5-dihydroxybenzoic acid).
Used in Synthesis of Complex Compounds:
In the field of synthesis, CMBZT is used as a ligand in the formation of new mixed ligand silver(I) chloride complexes. One such example is the synthesis of a complex with the heterocyclic thioamide CMBZT and tri(p-tolyl)phosphine, which has potential applications in various areas.
Used in Analysis of Peptidoglycan Muropeptides:
5-Chloro-2-mercaptobenzothiazole is also employed in the analysis of peptidoglycan muropeptides, which are essential components of bacterial cell walls. This application contributes to the understanding of bacterial cell wall structure and function, as well as the development of new antibiotics targeting these structures.

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

Upstream product

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

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 
• 23002-89-3 5-chloro-3-(4-phenyl-piperidin-1-ylmethyl)-3H-benzothiazole-2-thione 
• 39883-96-0 3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid methyl ester 
• 39883-95-9 3-[(5-chloro-2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoic acid ethyl ester 
• 23002-90-6 5-chloro-3-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-3H-benzothiazole-2-thione 
• 66858-94-4 5-chloro-3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzothiazole-2-thione 
• 23002-93-9 5-chloro-3-(4-fluoro-anilinomethyl)-3H-benzothiazole-2-thione 
• 3507-41-3 5-Chloro-2-(methylthio)benzothiazole 
• 97026-82-9 5-chloro-2-cyclohex-2-enylsulfanyl-benzothiazole 
• 74537-45-4 2-(5-chloro-benzothiazol-2-ylsulfanyl)-propionamide 

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.