66947-92-0

Basic information

• Product Name: 2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER
• Synonyms: VITAS-BB TBB000629;AKOS BBS-00000328;AKOS BC-3185;2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER;METHYL 2-AMINO-1,3-BENZOTHIAZOLE-6-CARBOXYLATE;IFLAB-BB F1981-0014;ASISCHEM D29190;6-Benzothiazolecarboxylicacid,2-amino-,methylester(9CI)
• CAS NO: 66947-92-0
• Molecular Formula: C₉H₈N₂O₂S
• Molecular Weight: 208.24
• Product Categories: BENZOTHIAZOLE
• Mol File: 66947-92-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 244-246
• Boiling Point: 378.4 °C at 760 mmHg
• Flash Point: 182.6 °C
• Appearance: /
• Density: 1.422
• Vapor Pressure: 6.31E-06mmHg at 25°C
• Refractive Index: 1.699
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.74±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER(66947-92-0)
• EPA Substance Registry System: 2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER(66947-92-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 66947-92-0(Hazardous Substances Data)

Usage

Description

2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER, also known as Methyl 2-amino-1,3-benzothiazole-6-carboxylate, is an organic compound that serves as a key reactant in the synthesis of various chemical products. It is characterized by its unique molecular structure, which includes a benzothiazole ring, an amino group, and a carboxylic acid ester group. This versatile chemical intermediate is known for its potential applications in the development of dyes and other specialty chemicals.

Uses

Used in Dye Industry:
2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID METHYL ESTER is used as a reactant in the preparation of azo-metal chelate dyes. It plays a crucial role in the synthesis of these dyes, which are known for their colorfastness, brightness, and resistance to fading. These dyes are widely used in various applications, including textiles, plastics, and printing inks, due to their superior properties and performance.

InChI:InChI=1/C9H8N2O2S/c1-13-8(12)5-2-3-6-7(4-5)14-9(10)11-6/h2-4H,1H3,(H2,10,11)

Upstream product

• 73931-63-2 methyl 1,3-benzothiazole-6-carboxylate 
• 3425-46-5 potassium selenocyanate 
• 540-72-7 sodium thiocyanide 
• 619-45-4 4-methoxycarbonyl aniline 
• 67-56-1 methanol 
• 93-85-6 2-aminobenzothiazole-6-carboxylic acid 
• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 90792-69-1 2-chlorobenzo[d]thiazole-6-carboxylic acid methyl ester 
• 1070908-14-3 2-(2-morpholin-4-yl-ethylamino)-benzothiazole-6-carboxylic acid [2-methyl-5-(3-trifluoromethyl-benzoylamino)-phenyl]-amide 
• 1070908-55-2 2-(5-fluoro-pyridin-2-ylamino)-benzothiazole-6-carboxylic acid [2-methyl-5-(3-trifluoromethyl-benzoylamino)-phenyl]-amide 
• 1070908-62-1 2-chloro-benzothiazole-6-carboxylic acid [2-methyl-5-(3-trifluoromethyl-benzoylamino)-phenyl]-amide 
• 14543-45-4 4-amino-3-mercaptobenzoic acid 
• 1620069-94-4 C₂₇H₂₀N₃O₅S^(1-)*Na⁽¹⁺⁾ 
• 1620069-92-2 C₂₇H₂₁N₃O₅S 
• 1620074-46-5 C₂₈H₂₃N₃O₅S 
• 1428621-61-7 methyl 2-[2-(4-methylbenzoylimino)-6-(phenylcarbamoyl)benzo[d]thiazol-3(2H)-yl]butanoate 
• 1428621-60-6 2-(4-methylbenzamido)-N-phenylbenzo[d]thiazol-6-carboxamide 
• 1428621-57-1 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylic acid 
• 1428621-58-2 methyl 3-(1-methoxy-1-oxobutan-2-yl)-2-(4-methylbenzoylimino)-2,3-dihydrobenzo[d]thiazol-6-carboxylate 
• 955569-38-7 methyl 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylate 
• 22514-58-5 2-bromobenzo[d]thiazole-6-carboxylic acid 

Relevant articles and documents

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Discovery and Optimization of Non-bile Acid FXR Agonists as Preclinical Candidates for the Treatment of Nonalcoholic Steatohepatitis

Farnesoid X receptor (FXR) plays a key role in bile acid homeostasis, inflammation, fibrosis, and metabolism of lipid and glucose and becomes a promising therapeutic target for nonalcoholic steatohepatitis (NASH) or other FXR-dependent diseases. The phase III trial results of obeticholic acid demonstrate that the FXR agonists emerge as a promising intervention in patients with NASH and fibrosis, but this bile acid-derived FXR agonist brings severe pruritus and an elevated risk of cardiovascular disease for patients. Herein, we reported our efforts in the discovery of a series of non-bile acid FXR agonists, and 36 compounds were designed and synthesized based on the structure-based drug design and structural optimization strategies. Particularly, compound 42 is a highly potent and selective FXR agonist, along with good pharmacokinetic profiles, high liver distribution, and preferable in vivo efficacy, indicating that it is a potential candidate for the treatment of NASH or other FXR-dependent diseases.

FXR regulator with spirane structure

The invention provides a new compound which has certain agonist activity on a Farnesoid X receptor (FXR) and is used for treating FXR mediated diseases and/or symptoms such as liver disease and gastrointestinal disease. (The formula is shown in the description.).