156454-43-2

Basic information

• Product Name: 5-BROMO-7-METHYL-1H-INDAZOLE
• Synonyms: 5-BROMO-7-METHYL-1H-INDAZOLE;TIMTEC-BB SBB002553;1H-Indazole, 5-bromo-7-methyl-
• CAS NO: 156454-43-2
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.06
• Product Categories: Halogenated Heterocycles;Heterocyclic Building Blocks;Indazoles
• Mol File: 156454-43-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 184-185°C
• Boiling Point: 346.22 °C at 760 mmHg
• Flash Point: 163.188 °C
• Appearance: /
• Density: 1.655 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.13±0.40(Predicted)
• CAS DataBase Reference: 5-BROMO-7-METHYL-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-7-METHYL-1H-INDAZOLE(156454-43-2)
• EPA Substance Registry System: 5-BROMO-7-METHYL-1H-INDAZOLE(156454-43-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 156454-43-2(Hazardous Substances Data)

Usage

General Description

5-bromo-7-methyl-1h-indazole is a chemical compound that belongs to the group of indazoles. Indazoles are organic compounds containing a bicyclic structural framework, which comprises a pyrazole ring fused with a benzene ring. In the case of 5-bromo-7-methyl-1h-indazole, it has a bromine atom at the 5th position and a methyl group at the 7th position of the indazole structure. This chemical is used as a building block in the synthesis of various advanced pharmaceutical and agrochemical compounds. The exact physical or chemical properties such as boiling point, melting point, toxicity or color can vary widely depending on its state, preparation method, or storage circumstances.

InChI:InChI=1/C8H7BrN2/c1-5-2-7(9)3-6-4-10-11-8(5)6/h2-4H,1H3,(H,10,11)

Upstream product

• 1424621-40-8 C₁₂H₁₇BrN₂ 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 943145-68-4 trans-4-bromo-2,6-dimethylphenyldiazo-tert-butyl sulfide 

Downstream Products

• 635712-41-3 C₂₀H₁₉N₃O₄ 
• 1146637-10-6 5-bromo-2,7-dimethyl-2H-indazole 
• 1613505-05-7 7-methyl-5-(2-(trifluoromethyl)phenyl)-1H-indazole 
• 1414976-17-2 methyl 2-benzamido-3-(7-methyl-1H-indazol-5-yl)-acrylate 
• 1414976-16-1 4-((7-methyl-1H-indazol-5-yl)methylene)-2-phenyloxazol-5(4H)-one 
• 1197938-68-3 2'-cyclohexyl-1-(7-methyl-1H-indazole-5-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one 
• 1197938-59-2 2'-benzyl-1-(7-methyl-1H-indazole-5-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one 
• 1031417-41-0 7-methyl-1H-indazole-5-carboxylic acid 
• 635712-40-2 7-methyl-1H-indazole-5-carbaldehyde 

Relevant articles and documents

A Novel Approach to 1H-Indazoles via Arylazosulfides

Treatment of variously substituted (o-alkylaryl)azosulfides 1a-n with potassium tert-butoxide in DMSO at room temperature smoothly furnishes 1H-indazoles 2a-n.

AUTOTAXIN INHIBITORS AND USES THEREOF

Described herein are methods and compositions for the treatment of conditions, diseases, or disorders associated with autotaxin activity. The methods and compositions disclosed herein include the use of at least one autotaxin inhibitor compound.

Discovery, optimization, and biological evaluation of 5-(2- (trifluoromethyl)phenyl)indazoles as a novel class of transient receptor potential A1 (TRPA1) antagonists

A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.