4-Nitro-1H-indazole Chemical Properties

Melting point:

199-203°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

11.08±0.40(Predicted)

Appearance

White to yellow Solid

InChI

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

InChIKey

WBTVZVUYPVQEIF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2942-40-7(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

Toxicity

mouse,LD50,intravenous,320mg/kg (320mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03515,

4-Nitro-1H-indazole Usage And Synthesis

Uses

4-Nitro-1H-indazole is a useful research chemical.

Chemical Properties

light yellow powder

Synthesis

General procedure for the synthesis of 4-nitroindazole from 2-methyl-3-nitroaniline: A. Preparation of 4-nitroindazole An aqueous sodium nitrite solution was prepared by dissolving sodium nitrite (20 g, 0.29 mol) in 50 mL of water. This aqueous sodium nitrite solution was added at once to a glacial acetic acid solution containing 2-methyl-3-nitroaniline (20 g, 0.13 mol) at 0 °C. The reaction system was vigorously stirred using an overhead stirrer. Immediately after the addition of sodium nitrite solution, precipitation generation was observed. Subsequently, the reaction mixture was gradually warmed up to room temperature and stirring was continued overnight. Upon completion of the reaction, the precipitate was separated by filtration and the filtrate was concentrated under vacuum. The resulting dark orange solid was suspended in water, filtered again and dried to give 14-21 g of dark orange solid product in 99% yield.

References

[1] Patent: US6534504, 2003, B1
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2752 - 2757
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2339 - 2352
[4] Organic Process Research and Development, 2007, vol. 11, # 3, p. 578 - 584
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 649 - 659

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