3-Amino-5-nitroindazole Chemical Properties

Melting point:

254-256°C

Boiling point:

485.2±25.0 °C(Predicted)

Density 

1.631±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

12.60±0.40(Predicted)

Appearance

Light brown to orange Solid

InChI

InChI=1S/C7H6N4O2/c8-7-5-3-4(11(12)13)1-2-6(5)9-10-7/h1-3H,(H3,8,9,10)

InChIKey

SWZRTDLKPZAFDT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

41339-17-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

3-Amino-5-nitroindazole Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-amino-5-nitroindazole from 2-fluoro-5-nitrobenzonitrile: 2-fluoro-5-nitrobenzonitrile (1.0 g, 6.02 mmol) was dissolved in n-butanol (20 mL). Subsequently, hydrazine hydrate (420 μL, 7.22 mmol) was added to this solution. The reaction mixture was stirred at 110 °C for 2 h and then cooled to room temperature. Dichloromethane (MC) was added to the reaction mixture and the precipitate precipitated was filtered to afford the target compound in 84% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.89 (d, 1H), 8.05 (dd, 1H), 7.34 (d, 2H), 5.98 (s, 2H). The molecular weight was measured as 178.15 by mass spectrometry.

References

[1] Patent: US2017/158642, 2017, A1. Location in patent: Paragraph 0075; 0076
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 23, p. 5293 - 5297
[3] Patent: US2004/9968, 2004, A1
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 550 - 554
[5] Patent: WO2013/55984, 2013, A1. Location in patent: Paragraph 00342

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