3-Nitro-1H-pyrazole Chemical Properties

Melting point:

173-175 °C

Boiling point:

334.0±15.0 °C(Predicted)

Density 

1.552±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.32±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C3H3N3O2/c7-6(8)3-1-2-4-5-3/h1-2H,(H,4,5)

InChIKey

MZRUFMBFIKGOAL-UHFFFAOYSA-N

SMILES

N1C=CC([N+]([O-])=O)=N1

CAS DataBase Reference

26621-44-3(CAS DataBase Reference)

NIST Chemistry Reference

3(5)-nitropyrazole(26621-44-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933199090

3-Nitro-1H-pyrazole Usage And Synthesis

Chemical Properties

light brown powder

Uses

3-Nitro-1H-pyrazole is a pyrazole compound with a nitro functional group, widely used in organic synthesis. The substance can be used in reaction systems such as substitution, nitration or condensation for the preparation of other heterocyclic compounds.

Synthesis

The general procedure for the synthesis of 3-nitro-1H-pyrazole from 1-nitropyrazole is as follows: Step A: 1-nitropyrazole (3.45 g, 30.5 mmol) was mixed with benzonitrile (33 mL) and heated with stirring at 180 °C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with hexane and stirring was continued for 20 min at room temperature. The precipitated solid was collected by filtration to afford 3-nitro-1H-pyrazole as a tan solid (3.16 g, 91% yield). Product characterization data: 1H NMR (300 MHz, DMSO-d6) δ 13.94 (br s, 1H), 8.03 (d, J = 2.4 Hz, 1H), 7.03 (t, J = 2.4 Hz, 1H).

References

[1] Archiv der Pharmazie, 1995, vol. 328, # 4, p. 349 - 358
[2] Patent: WO2010/29461, 2010, A1. Location in patent: Page/Page column 63-64
[3] Patent: WO2012/30944, 2012, A2. Location in patent: Page/Page column 97
[4] Patent: US2012/53174, 2012, A1. Location in patent: Page/Page column 45
[5] Patent: WO2012/30924, 2012, A1. Location in patent: Page/Page column 124

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