4-BROMO-2-METHYL-2H-INDAZOLE Chemical Properties

Boiling point:

322.7±15.0 °C(Predicted)

Density 

1.60±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-0.02±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H7BrN2/c1-11-5-6-7(9)3-2-4-8(6)10-11/h2-5H,1H3

InChIKey

OFOZLGCQBJDWRJ-UHFFFAOYSA-N

SMILES

N1=C2C(C(Br)=CC=C2)=CN1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2933998090

4-BROMO-2-METHYL-2H-INDAZOLE Usage And Synthesis

Uses

4-Bromo-2-methyl-2H-indazole is mainly used as a chemical reagent and organic synthesis intermediate in the field of scientific research.

Synthesis

The general procedure for the synthesis of 4-bromo-2-methyl-2H-indazole from trimethoxonium tetrafluoroborate and 4-bromo-1H-indazole was as follows: with reference to Example 33, 4-bromo-1H-indazole (2.24 g, 11.4 mmol) was dissolved in ethyl acetate (110 mL) and trimethoxonium tetrafluoroborate (2.19 g, 14.8 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was diluted with ethyl acetate, washed sequentially with aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=10/90→40/60) to afford 4-bromo-2-methyl-2H-indazole (2.29 g, 95% yield). The product was characterized by 1H-NMR (CDCl3): δ 4.23 (3H, s), 7.13 (1H, dd, J=8.5,7.2 Hz), 7.23 (1H, dd, J=7.2,0.8 Hz), 7.60-7.44 (1H, m), 7.91 (1H, m). The mass spectrum (ESI+) showed the molecular ion peak m/z 211 (M+H).

References

[1] Patent: EP2141150, 2010, A1. Location in patent: Page/Page column 63-64

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