4-bromo-1H-indazol-3-amine

Base Information

• Chemical Name: 4-bromo-1H-indazol-3-amine
• CAS No.: 914311-50-5
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.049
• Hs Code.: 29339980
• DSSTox Substance ID: DTXSID90475006
• Nikkaji Number: J2.390.684H
• Wikidata: Q72457204
• Mol file: 914311-50-5.mol

Synonyms:4-bromo-1H-indazol-3-amine;914311-50-5;3-AMINO-4-BROMO-1H-INDAZOLE;4-BROMO-1H-INDAZOL-3-YLAMINE;MFCD09909580;4-Bromo-2H-indazol-3-ylamine;SCHEMBL760018;4-Bromo-1H-indazole-3-amine;DTXSID90475006;IXXXOIXGQFPLIH-UHFFFAOYSA-N;BCP27097;AKOS005073920;AM90157;CS-W009221;N-Benzoyl-(3S,2R)-3-phenylisoserine;PB13089;4-bromo-1H-indazol-3-amine, AldrichCPR;AC-27137;SY027742;TS-03023;FT-0650453;EN300-318226;AS-813/43501668;J-514544;Z1269220695;3-Amino-4-bromo-1H-indazole

Chemical Property of 4-bromo-1H-indazol-3-amine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 142-144℃
• Refractive Index: 1.8
• Boiling Point: 431.342 °C at 760 mmHg
• PKA: 13.68±0.40(Predicted)
• Flash Point: 214.668 °C
• PSA: 54.70000
• Density: 1.867 g/cm³
• LogP: 2.48880
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Slightly soluble.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 210.97451
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Amino-4-bromo-1H-indazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)C(=NN2)N
• Uses: Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160°C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160°C, 10 min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones.

Technology Process of 4-bromo-1H-indazol-3-amine

There total 2 articles about 4-bromo-1H-indazol-3-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-bromo-6-fluorobenzaldehyde O-methyloxime → 4-bromo-3-amino-1H-indazole (914311-50-5) + 4-bromoindazole (186407-74-9)

Guidance literature:

With hydrazine; In 1,2-dimethoxyethane; Heating;

DOI:10.1021/jo0613784

Reference yield:

2-bromo-6-fluorobenzonitrile (79544-27-7) → 4-bromo-3-amino-1H-indazole (914311-50-5)

Guidance literature:

With hydrazine hydrate; In butan-1-ol; for 5h; Reflux;

DOI:10.1016/j.bmc.2010.11.020

Reference yield:

4-bromo-3-amino-1H-indazole (914311-50-5) → tert-butyl 4-[2-oxo-10-(2-oxo-1,3-oxazolidin-3-yl)-1,2-dihydropyrimido[1,2-b]indazol-4-yl]piperidine-1-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: potassium phosphate / 0.25 h / 180 °C / Microwave irradiation

2: dimethylaminoacetic acid; copper(l) iodide; potassium phosphate / N,N-dimethyl-formamide / 264 h / 100 °C / Inert atmosphere

With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid; In N,N-dimethyl-formamide;

upstream raw materials:

2-bromo-6-fluorobenzonitrile

Refernces

• 1、 -. "COMBINATION OF KINASE INHIBITORS AND USES THEREOF". Page/Page column 75. . Retrieved 2015/02/19.
• 2、 Sczewski, Franciszek,Kornicka, Anita,Hudson, Alan L.,Laird, Shayna,Scheinin, Mika,Laurila, Jonne M.,Rybczyńska, Apolonia,Boblewski, Konrad,Lehmann, Artur,Gdaniec, Maria. "3-[(Imidazolidin-2-yl)imino]indazole ligands with selectivity for the α2-adrenoceptor compared to the imidazoline I1 receptor". scheme or table. p. 321 - 329. Retrieved 2011/02/26.