3507-26-4

Basic information

• Product Name: 2-Chloro-6-methylbenzothiazole
• Synonyms: 6-METHYL-2-CHLORO BENZOTHIAZOLE;2-CHLORO-6-METHYLBENZOTHIAZOLE;2-CHLORO-6-METHYLBENZO[D]THIAZOLE;2-CHLORO-6-METHYL-1,3-BENZOTHIAZOLE;IFLAB-BB F1910-0010;Benzothiazole, 2-chloro-6-methyl- (6CI,7CI,8CI,9CI);2-Chloro-6-Methylbenzothiazole 96%
• CAS NO: 3507-26-4
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.66
• Product Categories: BENZOTHIAZOLE;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks
• Mol File: 3507-26-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 44-49 °C
• Boiling Point: 152°C/15mmHg(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.365g/cm³
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: 1.67
• Solubility: soluble in Methanol
• PKA: 0.25±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-6-methylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-6-methylbenzothiazole(3507-26-4)
• EPA Substance Registry System: 2-Chloro-6-methylbenzothiazole(3507-26-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3507-26-4(Hazardous Substances Data)

Usage

Description

2-Chloro-6-methylbenzothiazole is an organic compound that belongs to the benzothiazole family. It is characterized by a solid chemical structure, featuring a benzene ring fused with a thiazole ring, with a chlorine atom at the 2nd position and a methyl group at the 6th position. 2-Chloro-6-methylbenzothiazole is known for its versatile chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-methylbenzothiazole is used as a reactant and reagent for the synthesis and preparation of benzothiazole-based compounds. Specifically, it is utilized in the development of benzothiazole-π-piperazine derivatives, which serve as second-generation Non-Covalent NAAA Inhibitors. These inhibitors are designed to treat multiple sclerosis (MS) and other chronic disorders by targeting the NAAA enzyme, which plays a crucial role in the pathogenesis of these conditions.
Used in Chemical Synthesis:
As a versatile chemical compound, 2-Chloro-6-methylbenzothiazole is also used as an intermediate in the synthesis of various other organic compounds. Its unique structure allows it to be a valuable building block for creating a wide range of molecules with different properties and applications.
Used in Research and Development:
Due to its unique chemical properties and potential applications, 2-Chloro-6-methylbenzothiazole is often employed in research and development settings. Scientists and researchers use this compound to explore new chemical reactions, develop novel synthetic methods, and investigate its potential applications in various fields, including pharmaceuticals, materials science, and environmental chemistry.

InChI:InChI=1/C8H6ClNS/c1-5-2-3-6-7(4-5)11-8(9)10-6/h2-4H,1H3

Upstream product

• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 75-15-0 carbon disulfide 
• 106-49-0 p-toluidine 
• 10026-13-8 phosphorus pentachloride 
• 20174-69-0 2-hydrazino-6-methylbenzothiazole 
• 583-68-6 2-bromo-p-toluidine 
• 2268-79-3 2-mercapto-6-methylbenzothiazole 

Downstream Products

• 101281-22-5 methyl-(6-methyl-benzothiazol-2-yl)-p-tolyl-amine 
• 67058-58-6 6-methyl-2-phenylamino-1,3-benzothiazole 
• 85063-56-5 N-(4-ethoxyphenyl)-6-methylbenzo[d]thiazol-2-amine 
• 78072-95-4 methyl-(6-methyl-benzothiazol-2-yl)-phenyl-amine 
• 2369-32-6 6-methyl-N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 85063-54-3 (N-(4-bromophenyl)-6-methylbenzo[d]thiazol-2-amine) 
• 791594-39-3 (4-iodo-phenyl)-(6-methyl-benzothiazol-2-yl)-amine 
• 2268-79-3 6-methyl-1,3-benzothiazole-2(3H)-thione 
• 68194-97-8 [4-(6-methyl-benzothiazol-2-ylamino)-phenyl]-acetic acid 
• 78073-02-6 2-o-tolylimino-6-methylbenzothiazoline 
• 948588-53-2 C₁₇H₁₈N₂OS 
• 948588-55-4 C₂₇H₂₈N₂O₃S 
• 78073-00-4 2-o-tolylamino-3,6-dimethylbenzothiazoline 
• 3507-35-5 6-methyl-2-(methylthio)benzo[d]thiazole 

Relevant articles and documents

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles

Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.

Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles

In this work, we report the synthesis and characterization of new compounds derived from benzothiazoles and thiadiazoles. We observed that structural modifications on these skeletons affected the antioxidant activity. Thiol and aminothiol compounds derived from thiadiazoles and benzothiazoles showed an interesting antioxidant property. The radioprotective activity has also been evaluated in mice. Some of these compounds could be good radioprotectors.

Ferulic acid and benzothiazole dimer derivatives with high binding affinity to β-amyloid fibrils

New ferulic acid and benzothiazole dimer derivatives were synthesized and evaluated by in vitro competition assay using [125I]TZDM for their specific binding affinities to Aβ fibrils. In particular, 4a showed the most excellent binding affinity (Ki = 0.53 nM), compared to PIB (Ki = 0.77 nM), for benzothiazole binding sites of Aβ1-42 fibrils. This result suggests a possibility of a potential AD diagnostic probe for detection of Aβ fibrils.