7471-03-6

Basic information

• Product Name: 2-Amino-4-hydroxybenzothiazole
• Synonyms: 2-amino-4-hydroxy-benzothiazol;2-AMINOBENZO[D]THIAZOL-4-OL;2-AMINO-BENZOTHIAZOL-4-OL;2-AMINO-4-HYDROXYBENZOTHIAZOLE;2-AMINO-1,3-BENZOTHIAZOL-4-OL;4-Benzothiazolol,2-amino-(6CI,7CI,9CI);2-Amino-1,3-benzothiazol-4-ol, 4-Hydroxy-1,3-benzothiazole-2-amine;2-Amino-4-hydroxy-1,3-benzothiazole
• CAS NO: 7471-03-6
• Molecular Formula: C₇H₆N₂OS
• Molecular Weight: 166.2
• Product Categories: BENZOTHIAZOLE;Thiazole series
• Mol File: 7471-03-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 179-181°C
• Boiling Point: 394.6 °C at 760 mmHg
• Flash Point: 192.4 °C
• Appearance: /
• Density: 1.553 g/cm³
• Vapor Pressure: 8.61E-07mmHg at 25°C
• Refractive Index: 1.823
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 7.94±0.40(Predicted)
• CAS DataBase Reference: 2-Amino-4-hydroxybenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-hydroxybenzothiazole(7471-03-6)
• EPA Substance Registry System: 2-Amino-4-hydroxybenzothiazole(7471-03-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• RTECS: DL1800000
• Hazardous Substances Data: 7471-03-6(Hazardous Substances Data)

Usage

General Description

2-Amino-4-hydroxybenzothiazole, also known as 4-Aminophenol, is a chemical compound commonly used in the production of dyes and pigments. Its molecular structure consists of a benzene ring fused with a five-membered thiazole ring, with an amino and hydroxyl group attached at different positions. 2-Amino-4-hydroxybenzothiazole is known for its potential mutagenic and carcinogenic properties, and exposure to it may cause irritation to the skin, eyes, and respiratory system. In addition to its use in dye production, 2-Amino-4-hydroxybenzothiazole is also utilized in the synthesis of pharmaceuticals and as an intermediate in organic chemical reactions. Proper handling and precautions are necessary when working with this chemical due to its potential health hazards.

InChI:InChI=1/C7H6N2OS/c8-7-9-6-4(10)2-1-3-5(6)11-7/h1-3,10H,(H2,8,9)

Upstream product

• 5464-79-9 4-methoxy-1,3-benzothiazol-2-amine 
• 659731-49-4 acetic acid 2-acetylamino-benzothiazol-4-yl ester 
• 90180-68-0 4-methoxy-benzothiazol-2-ylamine hydrobromide 
• 1520-26-9 2-hydroxyphenylthiourea 
• 51-78-5 p-aminophenol hydrochloride 
• 333-20-0 potassium thioacyanate 
• 95-55-6 2-amino-phenol 

Downstream Products

• 19952-47-7 4-chlorobenzo[d]thiazol-2-amine 
• 659731-49-4 acetic acid 2-acetylamino-benzothiazol-4-yl ester 
• 879609-11-7 4-(2-chloro-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine 
• 1191251-66-7 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-5-ol 
• 1257262-15-9 4-(4-methylbenzyloxy)benzothiazol-2-ylamine 
• 1309261-62-8 3-(4-hydroxy-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 1309261-80-0 C₂₁H₁₄N₄O₂S 
• 659730-32-2 N-[4-[[6-[4-(trifluoromethyl)phenyl]-4-pyrimidinyl]oxy]-2-benzothiazolyl]acetamide 
• 20600-52-6 N-(4-hydroxybenzo[d]thiazol-2-yl)acetamide 

Relevant articles and documents

Optimization and biological evaluation of 2-aminobenzothiazole derivatives as Aurora B kinase inhibitors

A strong relationship between abnormal functions of Aurora kinases and tumorigenesis has been reported for decades. Consequently, Aurora kinases serve as potential targets for anticancer agents. Here, we identified aminobenzothiazole derivatives as novel inhibitors of Aurora B kinase through bioisosteric replacement of the previous inhibitors, aminobenzoxazole derivatives. Most of the urea-linked aminobenzothiazole derivatives showed potent and selective inhibitory activity against Aurora B kinase over Aurora A kinase. Molecular modeling indicated that compound 15g bound well to the active site of Aurora B kinase and formed the essential hydrogen bonds. The potent compounds, 15g and 15k, were selected, and their biological effects were evaluated using HeLa cell lines. It was found that these compounds inhibited the phosphorylation of histone H3 at Ser10 and induced G2/M cell cycle arrest. We suggest that the reported compounds have the potential to be further developed as anticancer therapeutics.

A novel system for the synthesis of 2-aminobenzthiazoles using sodium dichloroiodate

2-Aminobenzthiazole is a privileged scaffold with a range of biological activities. However, to date, an efficient protocol for the synthesis of this ring system using aniline as a starting material has been lacking. Herein, for the first time, we describe a highly efficient and mild protocol for the synthesis of 2-aminiobenzthiazole using NaICl Georg Thieme Verlag Stuttgart ? New York.

Design, synthesis and activity of benzothiazole-based inhibitors of NO production in LPS-activated macrophages

Series of benzothiazoles were synthesized and evaluated their inhibitory activities for NO production in lipopolysaccharide-activated macrophages. The most potent compound was the indole-containing benzothiazole 3c with 4.18 μM of IC50. The mec