1H-INDAZOLE-5-CARBONITRILE Chemical Properties

Boiling point:

370.3±15.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

Solid

pka

12.19±0.40(Predicted)

Appearance

Pink to red Solid

CAS DataBase Reference

74626-47-4

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29339900

1H-INDAZOLE-5-CARBONITRILE Usage And Synthesis

Chemical Properties

White solid

Synthesis

General procedure for the synthesis of indazole-5-carbonitrile from 4-fluoro-3-formylbenzonitrile: 4-fluoro-3-formylbenzonitrile (25 g, 16.78 mmol) was dissolved in 100 mL of 85% hydrazine hydrate. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the product was purified by column chromatography to afford 1H-indazole-5-carbonitrile (2.1 g, 87% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (ESI): 1H NMR δ 13.60 (s, 1H), 8.42 (s, 1H), 8.27 (s, 1H), 7.73 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 8.6 Hz, 1H); MS m/z (ESI): 144 [M + H]+.

References

[1] Patent: EP3205650, 2017, A1. Location in patent: Paragraph 0106; 0345
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4191 - 4195
[3] Synthetic Communications, 1997, vol. 27, # 7, p. 1199 - 1207
[4] Patent: US6376499, 2002, B1
[5] Patent: US6610692, 2003, B1

1H-INDAZOLE-5-CARBONITRILE(74626-47-4)Related Product Information

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• 6-INDAZOLYBORONIC ACID
• Ethyl indole-2-carboxylate
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