13382-43-9

Basic information

• Product Name: 5-AMINO-2-METHYLBENZOTHIAZOLE
• Synonyms: 2-Methylbenzo[d]thiazol-5-aMine;5-AMINO-2-METHYLBENZOTHIAZOLE;5-BENZOTHIAZOLAMINE, 2-METHYL-;2-METHYL-1,3-BENZOTHIAZOL-5-AMINE;5-Benzothiazolamine,2-methyl-(9CI);2-Methyl-1,3-benzothiazol-5-ylamine;5-Amino-2-methyl-1,3-benzothiazole;2-Methyl-5-aminobenzothiazole
• CAS NO: 13382-43-9
• Molecular Formula: C₈H₈N₂S
• Molecular Weight: 164.23
• Product Categories: BENZOTHIAZOLE
• Mol File: 13382-43-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 215℃
• Boiling Point: 325℃
• Flash Point: 150℃
• Appearance: /
• Density: 1.315
• Vapor Pressure: 0.000237mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: 2-8°C
• PKA: 3.10±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-2-METHYLBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-2-METHYLBENZOTHIAZOLE(13382-43-9)
• EPA Substance Registry System: 5-AMINO-2-METHYLBENZOTHIAZOLE(13382-43-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22-36
• Safety Statements: 22-26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 13382-43-9(Hazardous Substances Data)

Usage

Uses

5-Amino-2-methylbenzothiazole is used as pharmaceutical intermediates.

InChI:InChI=1/C8H8N2S/c1-5-10-7-4-6(9)2-3-8(7)11-5/h2-4H,9H2,1H3

Upstream product

• 68867-15-2 N-(2-methyl-1,3-benzothiazol-5-yl)acetamide 
• 2941-66-4 2-methyl-5-nitrobenzothiazole 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 10403-47-1 2-bromo 5-nitroaniline 
• 21715-13-9 2,4-diaminobenzenethiol 
• 90221-50-4 N-(2-bromo-5-nitrophenyl)acetamide 
• 7693-46-1 4-Nitrophenyl chloroformate 

Downstream Products

• 109806-37-3 2-methyl-5-(4t-phenyl-buta-1,3-dien-t-yl)-benzothiazole 
• 68867-15-2 N-(2-methyl-1,3-benzothiazol-5-yl)acetamide 
• 38463-33-1 2-Methylthiazolochinolin 
• 99069-39-3 dimethyl-(2-methyl-benzothiazol-5-yl)-amine 
• 20905-20-8 2-methyl-5-phenylazo-benzothiazole 
• 399-75-7 5-fluoro-2-methyl-1,3-benzothiazole 
• 56813-35-5 5-isothiocyanato-2-methyl-benzothiazole 
• 38875-12-6 2-methyl-4-thiocyanato-benzothiazol-5-ylamine 
• 5321-76-6 2-Methylthiazolo(5,4-g)benzo-1,2,3-thiadiazole 
• 5264-74-4 2,7-Dimethyl-benzo<1,2-d:3,4-d'>bis-thiazol 
• 36636-27-8 3-(2-methyl-benzothiazol-5-yl)-1-phenyl-triaz-2-enol 
• 92060-63-4 2-methyl-5-(4-nitro-phenyl)-benzothiazole 
• 90223-51-1 5-hydrazino-2-methyl-1,3-benzothiazole 
• 23085-29-2 5-azido-2-methyl-1,3-benzothiazole 

Relevant articles and documents

COMPOUNDS FOR TREATMENT OF TRYPANOSOMES AND NEUROLOGICAL PATHOGENS AND USES THEREOF

The present invention relates to novel compounds that cross the blood-brain barrier and are effective inhibitors of neurological pathogens such as trypanosomes. The invention further relates to the use of these compounds for treating disorders related to trypanosomes and neurological pathogens.

Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis

A previous publication from this lab (Patrick, et al. Bioorg. Med. Chem. 2016, 24, 2451-2465) explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole (1), which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogues, were quite potent, these molecules as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogues arising from medicinal chemistry optimization at different sites on the molecule. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analogue, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (57) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.

Nickel-catalyzed monoarylation of ammonia

Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.