3622-23-9

Basic information

• Product Name: 2,6-Dichlorobenzothiazole
• Synonyms: 2,6-DICHLORO-1,3-BENZOTHIAZOLE;2,6-DICHLOROBENZOTHIAZOLE;2,6-DICHLOROBENZO[D]THIAZOLE;IFLAB-BB F1910-0017;2,6-DichloroBenzothiazole98.5%;2,6-Dichlorobenzothiozole;Benzothiazole, 2,6-dichloro- (7CI,8CI,9CI);2,6-Dichlorobenzothioazole
• CAS NO: 3622-23-9
• Molecular Formula: C₇H₃Cl₂NS
• Molecular Weight: 204.08
• EINECS: 222-819-4
• Product Categories: BENZOTHIAZOLE;Sulphur Derivatives;Thiazoles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiazolesHeterocyclic Building Blocks
• Mol File: 3622-23-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 96-100 °C(lit.)
• Boiling Point: 286.8 °C at 760 mmHg
• Flash Point: 127.2 °C
• Appearance: powder
• Density: 1.567 g/cm³
• Vapor Pressure: 0.00446mmHg at 25°C
• Refractive Index: 1.701
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 127749
• CAS DataBase Reference: 2,6-Dichlorobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichlorobenzothiazole(3622-23-9)
• EPA Substance Registry System: 2,6-Dichlorobenzothiazole(3622-23-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3622-23-9(Hazardous Substances Data)

Usage

Description

2,6-Dichlorobenzothiazole is an organic compound characterized by its solid state and a chemical structure that features a benzene ring fused with a thiazole ring, with two chlorine atoms attached at the 2nd and 6th positions. 2,6-Dichlorobenzothiazole is known for its chemical stability and reactivity, making it a versatile building block in the synthesis of various organic molecules.

Uses

Used in Pharmaceutical Industry:
2,6-Dichlorobenzothiazole is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to be transformed into various derivatives with potential therapeutic applications. One such derivative is 6-chloro-2-(4-hydroxyphenoxy)benzothiazole, which may exhibit biological activities useful in the development of new drugs.
Used in Chemical Synthesis:
In the field of organic chemistry, 2,6-Dichlorobenzothiazole is used as a key building block for the creation of a wide range of chemical compounds. Its reactivity and stability make it a valuable component in the synthesis of various organic molecules, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, 2,6-Dichlorobenzothiazole is also utilized in research and development settings. It serves as a model compound for studying reaction mechanisms, exploring new synthetic routes, and testing the efficacy of various catalysts and reagents in organic reactions. This contributes to the advancement of chemical knowledge and the development of novel chemical processes.

InChI:InChI=1/C7H3Cl2NS/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H

Upstream product

• 95-24-9 6-chloro-2-aminobenzothiazole 
• 75-15-0 carbon disulfide 
• 106-47-8 4-chloro-aniline 
• 51618-29-2 6-chloro-2-mercaptobenzothiazole 
• 51011-54-2 6-chloro-2-hydrazinobenzothiazole 

Downstream Products

• 1190618-41-7 methyl (R)-2-(2-(2-(4-(4-(6-chloro-benzo[d]thiazol-2-ylamino)phenyl)pyridin-2-yl)hydrazino)-2-oxo-ethyl)-4-methyl-pentanoate 
• 1190618-34-8 methyl (S)-4-(2-(4-(4-(6-chloro-benzo[d]thiazol-2-ylamino)phenyl)pyridin-2-yl)hydrazino)-2-isopropyl-4-oxo-butanoate 
• 1190618-39-3 methyl (R)-4-(2-(4-(4-(6-chloro-benzo[d]thiazol-2-ylamino)phenyl)pyridin-2-yl)hydrazino)-2-isopropyl-4-oxo-butanoate 
• 1190618-33-7 (6-chloro-benzothiazol-2-yl)-[4-(2-hydrazino-pyridin-4-yl)-phenyl]-amine 
• 1190618-32-6 (6-chloro-benzothiazol-2-yl)-[4-(2-fluoro-pyridin-4-yl)-phenyl]-amine 
• 330793-95-8 6-chloro-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]thiazol-2-amine 
• 400802-64-4 1-[1-{3-[4-(6-Chloro-benzothiazol-2-yl)-piperazin-1-yl]-2-hydroxy-propyl}-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone 
• 252936-00-8 C₂₂H₁₆Cl₃N₇S 
• 95721-12-3 (2R)-2-{4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy}propanoic acid 
• 153025-29-7 6-chloro-2-piperazin-1-yl-benzothiazole 
• 34551-19-4 6-chloro-N-methylbenzo[d]thiazol-2-amine 
• 863001-13-2 C₁₈H₁₄Cl₂N₄S₂ 
• 1440509-65-8 C₁₅H₈ClNS 

Relevant articles and documents

Preparation method of 2,6'-dichlorobenzothiazole

The invention discloses a preparation method of 2,6'-dichlorobenzothiazole, and belongs to the technical field of organic chemistry. The method comprises the following steps: using 2-amino-6-chlorobenzothiazole as a raw material and acetonitrile as a solvent, adding copper chloride and isoamyl nitrite, carrying out a reaction to form a mixture of 2,6'-dichlorobenzothiazole and other impurities, and carrying out column chromatography separation to obtain pure 2,6'-dichlorobenzothiazole at a yield of 45-66%. The preparation method makes up for the deficiency of existing synthesis processes, andprovides a new method for synthesizing the 2,6'-dichlorobenzothiazole.

Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles

The 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazole scaffold was selected as a central core structure for the discovery of novel antibacterial compounds. A systematic variation of the substituents on the oxo-pyrazole moiety, as well as on the benzo moiety, led to the creation of a small and focused library of benzothiazoles that was subjected to antibacterial screening. In a first round of screening, activity of the compounds against six representative microorganisms was established. For the most potent congeners, MIC values against S. aureus and P. aeruginosa were determined. The structure-activity relationship study clearly revealed that subtle structural variations influence the antibacterial activity to a large extent. The most potent congeners displayed MIC values of 3.30 μM.

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.