3-Methyl-6-nitro-1H-indazole

Base Information

• Chemical Name: 3-Methyl-6-nitro-1H-indazole
• CAS No.: 6494-19-5
• Molecular Formula: C8H7N3O2
• Molecular Weight: 177.162
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID30448355
• Nikkaji Number: J1.156.167E
• Wikidata: Q72493572
• Mol file: 6494-19-5.mol

Synonyms:3-Methyl-6-nitro-1H-indazole;6494-19-5;3-Methyl-6-nitroindazole;3-methyl-6-nitro-2H-indazole;1313372-75-6;3-methyl-6-nitro-indazole;1H-INDAZOLE, 3-METHYL-6-NITRO-;2h-indazole,3-methyl-6-nitro-;MFCD07082704;6-nitro-3-methylindazole;SCHEMBL588431;DTXSID30448355;FUNWSYKLFDLUIZ-UHFFFAOYSA-N;BCP18726;CS-M3238;AKOS006336244;AKOS015842681;AKOS034830315;GS-3590;PB24959;SY017482;A8841;AM20050454;CS-0166802;FT-0649105;M2358;EN300-120877;F20398;J-512882

Chemical Property of 3-Methyl-6-nitro-1H-indazole

Chemical Property:

• Vapor Pressure: 0.00684mmHg at 25°C
• Melting Point: 187-188 °C
• Refractive Index: 1.704
• Boiling Point: 225.226 °C at 760 mmHg
• PKA: 11.47±0.40(Predicted)
• Flash Point: 90.014 °C
• PSA: 74.50000
• Density: 1.438 g/cm³
• LogP: 2.30270
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 177.053826475
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-6-nitroindazole ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC(=CC2=NN1)[N+](=O)[O-]
• Uses: 3-Methyl-6-nitroindazole a reactant used in the preparation of Pazopanib (P210925), an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

Technology Process of 3-Methyl-6-nitro-1H-indazole

There total 6 articles about 3-Methyl-6-nitro-1H-indazole 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: 98.0%

2-ethyl-5-nitroaniline (20191-74-6) → 3-methyl-6-nitro-1H-indazole (6494-19-5)

Guidance literature:

With acetic acid; isopentyl nitrite; at 20 ℃; for 0.75h;

DOI:10.1021/jm800566m

Reference yield: 98.0%

2-ethyl-5-nitroaniline (20191-74-6) → 3?methyl?6?nitro?1H?indazole (1313372-75-6,6494-19-5)

Guidance literature:

With tert.-butylnitrite; acetic acid;

Reference yield:

ortho-ethylaniline (578-54-1) → 3-methyl-6-nitro-1H-indazole (6494-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; potassium nitrate / 1.5 h / 0 °C

2: acetic acid; isopentyl nitrite / 1.5 h / 20 °C / Inert atmosphere

With sulfuric acid; acetic acid; potassium nitrate; isopentyl nitrite;

DOI:10.1016/j.cclet.2014.06.010

upstream raw materials:

2-ethyl-5-nitroaniline

ortho-ethylaniline

2-nitro(ethylbenzene)

Downstream raw materials:

3-methyl-1H-indazol-6-amine

3-methyl-1-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole

3-methyl-1-(3-methyl-5-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole

1-[3-(2-chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole

Refernces

• 1、 -. "Method for synthesizing 3-methyl-6-nitro-1H-indazole by microchannel diazo reaction". Paragraph 0027; 0028; 0029; 0030; 0031-0034. . Retrieved 2019/03/10.
• 2、 -. "2,3-dimethyl-6-urea -2H-indazoles and its preparation method and application". Paragraph 0125-0126; 0130-0132. . Retrieved 2016/10/09.