4-METHYL (1H)INDAZOLE Chemical Properties

Melting point:

114-116℃

Boiling point:

285.1±9.0 °C(Predicted)

Density 

1.186±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

14.47±0.40(Predicted)

Appearance

White to light yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

4-METHYL (1H)INDAZOLE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-methyl-1H-indazole from 2,3-dimethylaniline: Step A: Synthesis of 4-methyl-1H-indazole Tert-butyl nitrite (30 mL, 248 mmol) was slowly added to a solution of commercially available 2,3-dimethylaniline (20 mL, 165 mmol) in chloroform (600 mL) at room temperature and under nitrogen protection and the reaction mixture was stirred for 15 min. Subsequently, 18-crown-6 (4.3 g, 16.5 mmol) and potassium acetate (32 g, 333 mmol) were added and stirring was continued for 45 minutes. The reaction mixture was heated to reflux for 1 hour, then tert-butyl nitrite (10 mL, 82 mmol) was added and heating and refluxing was continued for 1 hour. After completion of the reaction, the mixture was cooled, the solid precipitate was removed by filtration, and the solids were washed with chloroform (3 x 200 mL). The filtrates were combined, washed with deionized water (400 mL) and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by fast column chromatography on silica gel with the eluent of petroleum ether/ethyl acetate (9:1, v/v) to afford 4-methyl-1H-indazole as an off-white solid (5.4 g, 25% yield). Product characterization data: 1H NMR (CDCl3) δ 2.7 (s, 3H), 6.90 (d, 1H), 7.50 (m, 2H), 8.10 (s, 1H).

References

[1] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 104-105
[2] Journal of Organic Chemistry, 1941, vol. 6, p. 427,431
[3] Helvetica Chimica Acta, 1979, vol. 62, p. 234,254
[4] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270

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