5-Nitroindazole Chemical Properties

Melting point:

207 °C

Boiling point:

383.3±15.0 °C(Predicted)

Density 

1.525±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.71±0.40(Predicted)

form 

powder to crystal

color 

White to Light red to Green

BRN 

7936

InChI

InChI=1S/C7H5N3O2/c11-10(12)6-1-2-7-5(3-6)4-8-9-7/h1-4H,(H,8,9)

InChIKey

WSGURAYTCUVDQL-UHFFFAOYSA-N

SMILES

N1C2=C(C=C([N+]([O-])=O)C=C2)C=N1

CAS DataBase Reference

5401-94-5(CAS DataBase Reference)

EPA Substance Registry System

5-Nitroindazole (5401-94-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-68-36-20/21/22

Safety Statements 

26-36/37/39

WGK Germany 

2

RTECS 

NK7962000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339990

MSDS

• Language:English Provider:5-Nitroindazole
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Nitroindazole Usage And Synthesis

Chemical Properties

light yellow crystal

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.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 21, p. 1063, 1984 DOI: 10.1002/jhet.5570210428
Organic Syntheses, Coll. Vol. 3, p. 660, 1955

Synthesis

General procedure: hydrazine hydrate (NH2NH2-H2O, 3.0 mmol) was added dropwise to a stirred solution of 2-fluoro-5-nitrobenzaldehyde (1.0 mmol) in DMF (5 mL) at 23 °C. The reaction mixture was stirred continuously at the same temperature for 2 h. The progress of the reaction was monitored by thin-layer chromatography (TLC, unfolding agent: 20% ethyl acetate in hexane solution) to confirm the complete conversion of the starting material 2-fluoro-5-nitrobenzaldehyde. Upon completion of the reaction, the crude reaction mixture was poured into water and extracted with ethyl acetate (2 x 15 mL). The organic phases were combined, washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give pure 5-nitroindazole.

References

[1] Molecules, 2018, vol. 23, # 3,
[2] Organic Process Research and Development, 2011, vol. 15, # 3, p. 565 - 569

5-Nitroindazole(5401-94-5)Related Product Information

• 4-Nitrobenzoic acid
• 3-Nitroacetophenone
• Nitroethane
• NITROGEN DIOXIDE
• 1-METHYL-5-NITROINDAZOLE
• 2-METHYL-5-NITRO-2H-INDAZOLE
• 3-Amino-5-nitroindazole
• 3-CHLORO-5-NITRO-1H-INDAZOLE
• Nitrobenzene
• TRITON
• 4-Nitrophenol
• Nitromethane
• 5-NITROINDAZOLE-3-CARBOXYLIC ACID
• 2,3-DIMETHYL-6-NITRO-2H-INDAZOLE
• 6-Nitroindazole
• 3-BROMO-7-NITROINDAZOLE
• 3-IODO-6-NITROINDAZOLE
• 3-BROMO-5-NITROINDAZOLE