2-METHYL-5-NITRO-2H-INDAZOLE Chemical Properties

Melting point:

129-131°C

storage temp. 

Sealed in dry,Room Temperature

form 

powder

color 

Yellow

BRN 

167044

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:ALFA

2-METHYL-5-NITRO-2H-INDAZOLE Usage And Synthesis

Synthesis

GENERAL METHOD: Cesium carbonate (12.26 mmol) was added to a tetrahydrofuran (THF; 25 mL) solution of 5-nitroindazole (6.13 mmol) cooled at 0 °C. After stirring for 15 min at 0 °C, iodomethane or allyl bromide (6.13 mmol) was added dropwise. The reaction was monitored by thin layer chromatography (TLC) until the starting material disappeared. Subsequently, the reaction mixture was concentrated by evaporation. The crude product was dissolved in ethyl acetate (EtOAc; 50 mL), washed sequentially with water and brine, and dried over anhydrous magnesium sulfate (MgSO?). After removal of the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography with ethyl acetate/hexane (3:7, v/v) as eluent to afford 1-alkyl-5-nitroindazole and 2-alkyl-5-nitroindazole, respectively.

References

[1] Synthetic Communications, 2015, vol. 45, # 17, p. 2005 - 2013
[2] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[3] Patent: US2014/371219, 2014, A1. Location in patent: Paragraph 0659; 0660; 0661
[4] Patent: WO2016/57834, 2016, A1. Location in patent: Paragraph 000406

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