2,3-DIMETHYL-2H-INDAZOL-6-AMINE

Base Information

• Chemical Name: 2,3-DIMETHYL-2H-INDAZOL-6-AMINE
• CAS No.: 444731-72-0
• Molecular Formula: C9H11N3
• Molecular Weight: 161.206
• Hs Code.: 2922390090
• Mol file: 444731-72-0.mol

Synonyms:6-Amino-2,3-dimethyl-2H-indazole;

Chemical Property of 2,3-DIMETHYL-2H-INDAZOL-6-AMINE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Boiling Point: 366.91 °C at 760 mmHg
• PKA: 4.20±0.30(Predicted)
• Flash Point: 175.701 °C
• PSA: 43.84000
• Density: 1.232 g/cm³
• LogP: 2.04510

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dimethyl-6-amino-2H-indazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3-Dimethyl-6-amino-2H-indazole is an impurity in the synthesis of Pazopanib (P210925) hydrochloride, an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

Technology Process of 2,3-DIMETHYL-2H-INDAZOL-6-AMINE

There total 8 articles about 2,3-DIMETHYL-2H-INDAZOL-6-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: 96.7%

2,3?dimethyl?6?nitro?2H?indazole (444731-73-1) → 2,3-dimethyl-6-amino-2H-indazole (444731-72-0)

Guidance literature:

With ammonium formate; palladium 10% on activated carbon; In methanol; water; at 25 - 30 ℃; for 6h;

Reference yield: 96.7%

3-methyl-6-nitro-1H-indazole (6494-19-5) → 2,3-dimethyl-6-amino-2H-indazole (444731-72-0)

Guidance literature:

With ammonium formate; palladium 10% on activated carbon; In methanol; water; at 25 - 30 ℃; for 6h;

Reference yield:

2-ethyl-5-nitroaniline (20191-74-6) → 2,3-dimethyl-6-amino-2H-indazole (444731-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; sodium nitrite / water / 0.5 h / 35 °C

2: sulfuric acid / N,N-dimethyl-formamide; toluene / 3 h / Reflux

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol

With sulfuric acid; palladium 10% on activated carbon; hydrogen; acetic acid; sodium nitrite; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.2174/157017812800233714

upstream raw materials:

2,3?dimethyl?6?nitro?2H?indazole

3-methyl-6-nitro-1H-indazole

2-ethyl-5-nitroaniline

ortho-ethylaniline

Downstream raw materials:

N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine

pazopanib

N,2,3-trimethyl-2H-indazole-6-amine

N-carbamimidoyl-4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)benzenesulfonamide

Refernces

• 1、 Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.. "High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates". supporting information. p. 8114 - 8118. Retrieved 2021/10/25.
• 2、 -. "Method for synthesizing 2,3-dimethyl-6-amino-2H-indazole by microchannel hydrogenation". Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031; 0032. . Retrieved 2019/03/10.