3-CHLORO-6-NITRO (1H)INDAZOLE Chemical Properties

Melting point:

203-205

Boiling point:

415.2±25.0 °C(Predicted)

Density 

1.661±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.01±0.40(Predicted)

form 

solid

color 

Yellow

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

29339900

3-CHLORO-6-NITRO (1H)INDAZOLE Usage And Synthesis

Chemical Properties

Yellow solid

Synthesis

General procedure for the synthesis of 3-chloro-6-nitro-1H-indazole from 6-nitro-1H-indazole: 6-nitro-1H-indazole (5.0 g, 31 mmol) was added to an aqueous (150 mL) solution of sodium hydroxide (5.0 g), and the mixture was heated until a red color solution formed. The reaction mixture was cooled in an ice water bath for 15 minutes, followed by the slow addition of sodium hypochlorite solution (60 mL, 5.25%, 45 mmol). The reaction mixture was stirred continuously at 0 °C for 5 h. Upon completion of the reaction, the pH was adjusted with dilute hydrochloric acid to 7. The reaction mixture was extracted with ethyl acetate, the organic layers were combined and washed with distilled water, followed by concentration of the organic phase under reduced pressure. The residue was purified by fast column chromatography to afford the target product 3-chloro-6-nitro-1H-indazole (5.5 g, 92% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 7.93 (m, 1H), 8.02 (m, 1H), 8.50 (m, 1H), 14.01 (s, 1H); the mass spectrum (DCI/NH3) showed m/z 197 [M+H]+.

References

[1] Patent: US2005/277638, 2005, A1. Location in patent: Page/Page column 49
[2] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
[3] Heterocycles, 1995, vol. 41, # 3, p. 487 - 496
[4] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 285,302
[5] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 285,302

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