1629-78-3

Basic information

• Product Name: 2-Acetylbenzothiazole
• Synonyms: 1,3-BENZOTHIAZOLE-2-CARBOXALDEHYDE;1-(1,3-BENZOTHIAZOL-2-YL)ETHANONE;2-ACETYLBENZOTHIAZOLE;AKOS BBS-00006878;BENZOTHIAZOLE-2-CARBALDEHYDE;BENZOTHIAZOLE-2-CARBOXALDEHYDE;RARECHEM AM LA 0033;Ethanone, 1-(2-benzothiazolyl)- (9CI)
• CAS NO: 1629-78-3
• Molecular Formula: C₉H₇NOS
• Molecular Weight: 163.2
• Product Categories: BENZOTHIAZOLE
• Mol File: 1629-78-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 109 °C
• Boiling Point: 301.9 °C at 760 mmHg
• Flash Point: 136.4 °C
• Appearance: off-white to yellow crystalline solid
• Density: 1.286 g/cm³
• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: 2-8°C
• PKA: -1.49±0.10(Predicted)
• CAS DataBase Reference: 2-Acetylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetylbenzothiazole(1629-78-3)
• EPA Substance Registry System: 2-Acetylbenzothiazole(1629-78-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 1629-78-3(Hazardous Substances Data)

Usage

General Description

2-Acetylbenzothiazole is a chemical compound with the molecular formula C9H7NOS. It’s an aromatic heterocyclic compound that combines benzene and thiazole rings with an acetyl functional group. It has a molar mass of 177.23 g/mol. Known for its characteristic offensive smell, it is used mainly as an intermediate in the preparation of compounds that act as ultraviolet light absorbers, making it useful in the production of materials that require protection from UV radiation. Potential applications include usage in industries like textiles, plastics, and cosmetics. Like all chemicals, however, it should be handled with care, as it is hazardous in case of inhalation, ingestion, or skin and eye contact, and should thus be stored and disposed of properly.

InChI:InChI=1/C9H7NOS/c1-6(11)9-10-7-4-2-3-5-8(7)12-9/h2-5H,1H3

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 75-07-0 acetaldehyde 
• 127-19-5 N,N-dimethyl acetamide 
• 541-46-8 isobutylamide 
• 75-36-5 acetyl chloride 
• 175694-99-2 (2-isocyanophenyl)(methyl)sulfane 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 762-04-9 phosphonic acid diethyl ester 
• 60490-70-2 2-phenylazo-benzenesulfenyl chloride 
• 67-64-1 acetone 
• 17147-80-7 2-(1-hydroxyethyl)-1,3-benzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 16414-04-3 1-benzimidazol-2-ylethanol 
• 110-05-4 di-tert-butyl peroxide 

Downstream Products

• 54223-20-0 1-(benzo[d]thiazol-2-yl)-2-bromoethanone 
• 94834-02-3 1-(6-nitrobenzo[d]thiazol-2-yl)ethanone 
• 1253901-27-7 1-(benzo[d]thiazol-2-yl)-1-(4-chloro-2-methylphenyl)ethanol 
• 1253901-21-1 1-(benzo[d]thiazol-2-yl)-1-(naphtalen-2-yl)ethanol 
• 1253901-25-5 1-(benzo[d]thiazol-2-yl)-1-(4-fluoro-3-methylphenyl)ethanol 
• 54469-55-5 4-(benzo[d]thiazol-2-yl)-N-phenylthiazol-2-amine 
• 66730-39-0 2-(prop-1-en-2-yl)benzo[d]thiazole 
• 433924-37-9 (S)-2-(benzo[d]thiazol-2-yl)pent-4-en-2-ol 
• 17147-80-7 2-(1-hydroxyethyl)-1,3-benzothiazole 
• 453558-32-2 1-(benzo[d]thiazol-2-yl)-2-chloroethanone 
• 1433956-01-4 1-(1,3-benzothiazol-2-yl)-4-nitro-3-phenylbutan-1-one 
• 1433955-73-7 (R)-1-(1,3-benzothiazol-2-yl)-4-nitro-3-phenylbutan-1-one 

Relevant articles and documents

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

Neutral analogs of the heat shock protein 70 (Hsp70) inhibitor, JG-98

The heat shock protein 70 (Hsp70) family of molecular chaperones are highly expressed in tumors. Inhibitors containing a pyridinium-modified benzothiazole, such as JG-98, bind to a conserved, allosteric site in Hsp70, showing promising anti-proliferative activity in cancer cells. When bound to Hsp70, the charged pyridinium makes favorable contacts; however, this moiety also increases the inhibitor's fluorescence, giving rise to undesirable interference in biochemical and cell-based assays. Here, we explore whether the pyridinium can be replaced with a neutral pyridine. We report that pyridine-modified benzothiazoles, such as compound 17h (JG2-38), have reduced fluorescence, yet retain promising anti-proliferative activity (EC50 values ~0.1 to 0.07 μM) in breast and prostate cancer cell lines. These chemical probes are expected to be useful in exploring the roles of Hsp70s in tumorigenesis and cell survival.

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.