3622-38-6

Basic information

• Product Name: Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI)
• Synonyms: Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI);Benzothiazole, 2-chloro-5-nitro-;2-chloro-5-nitrobenzo[d]thiazole;2-Chloro-5-nitrobenzothiazole;2-chloro-5-nitro-1,3-benzothiazole
• CAS NO: 3622-38-6
• Molecular Formula: C₇H₃ClN₂O₂S
• Molecular Weight: 214.62892
• Product Categories: BENZOTHIAZOLE
• Mol File: 3622-38-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 348.1 °C at 760 mmHg
• Flash Point: 164.3 °C
• Appearance: /
• Density: 1.65 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.732
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI)(3622-38-6)
• EPA Substance Registry System: Benzothiazole, 2-chloro-5-nitro- (7CI,8CI,9CI)(3622-38-6)

Safety Data

• Hazardous Substances Data: 3622-38-6(Hazardous Substances Data)

Usage

General Description

Benzothiazole, 2-chloro-5-nitro- is a chemical compound with the molecular formula C7H4ClN3O2. It is a derivative of benzothiazole, which is commonly used in the production of dyes, optical brighteners, and pharmaceuticals. The 2-chloro-5-nitro- substitution on the benzothiazole ring adds specific chemical properties that make it useful in various applications, including as a building block for the synthesis of other compounds. The presence of the chlorine and nitro groups in the molecule can affect its reactivity and behavior in different chemical reactions, making it an important compound in the field of organic chemistry.

InChI:InChI=1/C7H3ClN2O2S/c8-7-9-5-3-4(10(11)12)1-2-6(5)13-7/h1-3H

Upstream product

• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 369-36-8 6-fluoro-3-nitroaniline 
• 73458-39-6 5-nitro-benzothiazol-2-ylamine 
• 80945-80-8 (5-nitro-benzothiazol-2-yl)-hydrazine 
• 58759-63-0 5-nitro-2-mercaptobenzothiazole 

Downstream Products

• 80945-82-0 2-chlorobenzo[d]thiazol-5-amine 
• 939795-71-8 C₁₉H₂₀N₄O₂S 
• 939795-72-9 C₁₉H₁₉N₄O₂SF 
• 38519-82-3 N-{2-[4-(2-diethylamino-ethoxy)-anilino]-benzothiazol-5-yl}-acetamide 
• 939795-82-1 C₁₉H₂₁N₄SF 
• 939795-81-0 C₁₉H₂₂N₄S 

Relevant articles and documents

Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof

The present invention provides compounds that can enhance functional O-mannosylation of proteins including alpha-dystroglycan. Also provided are methods of preparation of the compounds defined by the formula I. Also provided are the methods of using the compounds or the pharmaceutical acceptable salts or prodrugs thereof in treating and preventing subjects suffering from the diseases including muscular dystrophies and cancers.

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of α-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy.

A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles

A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-ethyl dithiocarbonate under mild conditions. Subsequent intra-molecular cyclization affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily converted to corresponding 2-chlorobenzothiazoles upon treatment with sulfuryl chloride.