61272-71-7

Basic information

• Product Name: 5-BROMO-1H-INDAZOL-3-AMINE
• Synonyms: 5-BROMO-1H-INDAZOL-3-AMINE;5-BROMO-1H-INDAZOL-3-YLAMINE;5-Bromo-1H-indazol-3-amine 95%;5-bromo-1H-indazol-3-amine (en);3-Amino-5-bromo-1H-indazole;3-Amino-5-bromoindazole;3-Amino-5-bromo-1H-indazole 95%;5-bromo-1H-indazol-3-amine(SALTDATA: FREE)
• CAS NO: 61272-71-7
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.05
• Product Categories: Amines;Fused Ring Systems
• Mol File: 61272-71-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 171-175
• Boiling Point: 431.3 °C at 760 mmHg
• Flash Point: 214.7 °C
• Appearance: Clear colorless/Liquid
• Density: 1.867g/cm³
• Vapor Pressure: 1.21E-07mmHg at 25°C
• Refractive Index: 1.8
• Storage Temp.: Room temperature.
• PKA: 13?+-.0.40(Predicted)
• CAS DataBase Reference: 5-BROMO-1H-INDAZOL-3-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-INDAZOL-3-AMINE(61272-71-7)
• EPA Substance Registry System: 5-BROMO-1H-INDAZOL-3-AMINE(61272-71-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-36/37/38-22
• Safety Statements: 45-36/37/39-26-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 61272-71-7(Hazardous Substances Data)

Usage

Description

5-BROMO-1H-INDAZOL-3-AMINE is an organic compound with the molecular formula C7H6BrN3. It is a derivative of indazole, a tricyclic aromatic compound, and features a bromine atom at the 5th position. 5-BROMO-1H-INDAZOL-3-AMINE is known for its potential applications in various chemical and pharmaceutical processes due to its unique chemical structure.

Uses

Used in Organic Synthesis:
5-BROMO-1H-INDAZOL-3-AMINE is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of advanced organic compounds.
Used in Pharmaceutical Industry:
5-BROMO-1H-INDAZOL-3-AMINE is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and therapeutic agents. Its chemical properties enable it to be incorporated into the structures of potential pharmaceutical compounds, contributing to their overall efficacy and function.
Used in Laboratory Research and Development:
5-BROMO-1H-INDAZOL-3-AMINE is utilized in laboratory research and development processes, where it serves as a key component in the exploration of new chemical reactions and the synthesis of novel compounds. Its presence in the lab allows researchers to study its reactivity and potential applications in various chemical and biological contexts.
Used in Chemical Production Process:
In the chemical production process, 5-BROMO-1H-INDAZOL-3-AMINE is employed as an intermediate to produce a range of chemical products. Its versatility and reactivity make it a valuable asset in the manufacturing of various chemicals, contributing to the overall efficiency and effectiveness of the production process.

Synthesis

Hydrazine hydrate (18 mL) was added to Example 62C (1.93 g, 6.94 mmol.) in ethanol (10 mL). The mixture was heated to 95°C. overnight. The mixture was diluted with ethyl acetate and washed with water. Some of the product precipitated in the separatory funnel and was filtered to afford the title compound. The ethyl acetate layer was concentrated under reduced pressure and the resulting solid was triturated with methanol. 5-bromo-1H-indazol-3-amine. The title compound was prepared according to the procedure outlined in Example 62D substituting 5-bromo-2-fluorobenzonitrile for Example 62C. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (s, 1H), 7.92 (d, J=1.87 Hz, 1H), 7.30 (dd, J=8.79, 1.89 Hz, 1H), 7.19 (d, J=8.78 Hz, 1H), 5.41 (s, 2H).

InChI:InChI=1/C7H6BrN3/c8-4-1-2-6-5(3-4)7(9)11-10-6/h1-3H,(H3,9,10,11)

Upstream product

• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 39263-32-6 2-amino-5-bromobenzonitrile 

Downstream Products

• 1093965-09-3 5-(1-methyl-1H-pyrazol-4-yl)-1H-indazol-3-amine 
• 1036380-75-2 3-amino-5-bromobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 1432912-73-6 tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)-(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1H-indazole-1-carboxylate 
• 1432912-66-7 tert-butyl 3-[bis(tert-butoxycarbonyl)amino]-5-(5-chloro-2-hydroxyphenyl)-1H-indazole-1-carboxylate 

Relevant articles and documents

SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE

The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

Fragment-based discovery of JAK-2 inhibitors

Fragment-based hit identification coupled with crystallographically enabled structure-based drug design was used to design potent inhibitors of JAK-2. After two iterations from fragment 1, we were able to increase potency by greater than 500-fold to provide sulfonamide 13, a 78-nM JAK-2 inhibitor.

5-HETEROARYL SUBSTITUTED INDAZOLES AS KINASE INHIBITORS

The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein A, R1, R2, R3 and m, are defined in the description. The present invention relates also to methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as Glycogen Synthase kinase 3 (GSK-3), Rho kinase (ROCK), Janus Kinases (JAK), AKT, PAK4, PLK, CK2, KDR, MK2, JNK1, aurora, pim 1 and nek 2.