1-METHYL-5-NITRO-1H-INDAZOLE Chemical Properties

Melting point:

161-162°C

Boiling point:

332.9±15.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-0.82±0.30(Predicted)

color 

yellow

BRN 

168080

CAS DataBase Reference

5228-49-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/22-68

Safety Statements 

22-36/37

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

II

HS Code 

2933998090

MSDS

• Language:English Provider:ALFA

1-METHYL-5-NITRO-1H-INDAZOLE Usage And Synthesis

Synthesis

GENERAL METHOD: Cesium carbonate (12.26 mmol) was added to a solution of 5-nitroindazole (6.13 mmol) in tetrahydrofuran (THF; 25 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 15 min before iodomethane or allyl bromide (6.13 mmol) was added dropwise. The progress of the reaction was monitored by thin layer chromatography (TLC) until the starting material completely disappeared. After completion of the reaction, the mixture was concentrated. The crude product was dissolved in ethyl acetate (EtOAc; 50 mL), washed sequentially with water and brine, and the organic phase was dried over anhydrous magnesium sulfate (MgSO?). The solvent was removed by evaporation under reduced pressure, and 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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