133044-44-7

Basic information

• Product Name: 2(3H)-Benzothiazolone,6-acetyl-(9CI)
• Synonyms: 6-acetylbenzo[d]thiazol-2(3H)-one;6-Acetylbenzo[d]thiazol-2(3H);2(3H)-Benzothiazolone,6-acetyl-(9CI);6-acetyl-1,3-benzothiazole-2(3)-one
• CAS NO: 133044-44-7
• Molecular Formula: C₉H₇NO₂S
• Molecular Weight: 193.225
• EINECS: 1312995-182-4
• Product Categories: BENZOTHIAZOLE
• Mol File: 133044-44-7.mol

Chemical Properties

• Melting Point: 190-194°C
• Appearance: /
• Density: 1.36 g/cm³
• Refractive Index: 1.635
• PKA: 9.76±0.20(Predicted)
• CAS DataBase Reference: 2(3H)-Benzothiazolone,6-acetyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzothiazolone,6-acetyl-(9CI)(133044-44-7)
• EPA Substance Registry System: 2(3H)-Benzothiazolone,6-acetyl-(9CI)(133044-44-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 133044-44-7(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C9H7NO2S/c1-5(11)6-2-3-7-8(4-6)13-9(12)10-7/h2-4H,1H3,(H,10,12)

Upstream product

• 1373399-25-7 C₁₁H₁₂INO₃ 
• 934-34-9 2(3H)-Benzothiazolone 
• 51360-57-7 3-acetyl-2(3H)-benzothiazolone 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Benzo[d]thiazol-2(3H)-ones as new potent selective CB2 agonists with anti-inflammatory properties

The high distribution of CB2 receptors in immune cells suggests their important role in the control of inflammation. Growing evidence offers this receptor as an attractive therapeutic target: selective CB2 agonists are able to modula

Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression

A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an

CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide

A copper-catalyzed procedure was developed for assembling benzothiazolones from ethyl 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields.

Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives

A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]

Application of the "fries like" rearrangement using ZnCL 2 for the synthesis of 6-acyl-2(3H)-benzothiazolones

In this work we report another method of acylation on the 6-position of the 2(3H)-benzothiazolone ring with Fries-like rearrangement catalyzed by zinc chloride instead of aluminium chloride and 3-acyl-2(3H)-benzothiazolones derivatives as starting materia

Study of the acylation reaction of 2(3H)-benzothiazolones in the mixture of ZnCl2-DMF

The use of polyphosphoric acid and the complex AlCl3-DMF in 6-acylation of 2(3H)-benzothiazolones previously have been reported. Instead of the frequently used AlCl3 as a catalyst in the Friedl-Crafts reactions, we conducted the acyl

'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.

Benzothiazolinone compounds

Compounds of general formula (I): STR1 in which: R1 represents a hydrogen atom or a lower alkyl group, R2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstitute