5-Nitroindazole

Base Information

• Chemical Name: 5-Nitroindazole
• CAS No.: 5401-94-5
• Molecular Formula: C7H5N3O2
• Molecular Weight: 163.136
• Hs Code.: 29339990
• European Community (EC) Number: 226-451-5
• NSC Number: 5032
• UNII: 235Y7P37ZD
• DSSTox Substance ID: DTXSID5049316
• Nikkaji Number: J2.232B
• Wikidata: Q27253724
• Metabolomics Workbench ID: 148978
• ChEMBL ID: CHEMBL165372
• Mol file: 5401-94-5.mol

Synonyms:5-nitro-1H-indazole;5-nitroindazole

Chemical Property of 5-Nitroindazole

Chemical Property:

• Appearance/Colour: light yellow crystal
• Vapor Pressure: 9.79E-06mmHg at 25°C
• Melting Point: 207 °C
• Refractive Index: 1.74
• Boiling Point: 383.3 °C at 760 mmHg
• PKA: 11.71±0.40(Predicted)
• Flash Point: 185.6 °C
• PSA: 74.50000
• Density: 1.525 g/cm³
• LogP: 1.99430
• Storage Temp.: Store below +30°C.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 163.038176411
• Heavy Atom Count: 12
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

5-Nitroindazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-68-36-20/21/22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C=NN2
• Uses: 5-Nitroindazole inhibits citrulline formation by Ca2+-calmodulin (CaM)-dependent nitric oxide synthase from bovine brain. Nitration of 5-nitroindazole with nitric acid and acetic anhydride yields 3,5-dintroindazole and 2,5-dinitroindazole.

Technology Process of 5-Nitroindazole

There total 14 articles about 5-Nitroindazole 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: 100.0%

2-methyl-4-nitro-benzenamine (99-52-5) → 5-nitroindazole (5401-94-5)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 0 - 20 ℃; for 72h;

Reference yield: 99.0%

5-nitro-indazole-1-carboxylic acid tert-butyl ester (129488-09-1) → 5-nitroindazole (5401-94-5)

Guidance literature:

In methanol; at 120 ℃; for 0.333333h; under 5171.62 Torr; Microwave irradiation;

DOI:10.1016/j.tetlet.2008.12.074

Reference yield: 90.0%

2-fluoro-5-nitrobenzaldehye (27996-87-8) → 5-nitroindazole (5401-94-5)

Guidance literature:

With hydrazine hydrate; In N,N-dimethyl-formamide; at 23 ℃; for 2h; Inert atmosphere;

DOI:10.3390/molecules23030674

upstream raw materials:

benzimidazole

2-methyl-4-nitro-benzenamine

nitric acid

5-nitro-indazole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

C₁₆H₉N₃O₄

1-ethyl-5-nitro-1H-indazole

5-Nitro-indazole-1-carboxylic acid (2-fluoro-phenyl)-amide

Refernces

• 1、 Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei. "A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides". supporting information. . Retrieved 2020/10/05.
• 2、 Elsayed, Nevine M.Y.,Serya, Rabah A.T.,Tolba, Mai F.,Ahmed, Marawan,Barakat, Khaled,Abou El Ella, Dalal A.,Abouzid, Khaled A.M.. "Design, synthesis, biological evaluation and dynamics simulation of indazole derivatives with antiangiogenic and antiproliferative anticancer activity". . p. 340 - 359. Retrieved 2018/11/23.