1-(1H-INDAZOL-3-YL)ETHANONE Chemical Properties

Melting point:

182 °C

Boiling point:

348.8±15.0 °C(Predicted)

Density 

1.264±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.87±0.40(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

1-(1H-INDAZOL-3-YL)ETHANONE Usage And Synthesis

Synthesis Reference(s)

Synthesis, p. 937, 1992 DOI: 10.1055/s-1992-26268

Synthesis

GENERAL STEPS: To an anhydrous THF solution of N-methoxy-N-methyl-1H-indazole-3-carboxamide (950 mg, 4.63 mmol, 1.1 eq.), the mixture was cooled to 0 °C. Methylmagnesium bromide (7.7 mL, 23.17 mmol, 5.0 eq.) was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of NH4Cl solution (5 mL). Subsequently, the solvent was removed by distillation under reduced pressure and the obtained residue was purified by column chromatography (eluent: ethyl acetate/petroleum ether = 1/2) to afford 1-(1H-indazol-3-yl)ethanone (610 mg, 82.3% yield) as a yellow solid.

References

[1] Tetrahedron, 2007, vol. 63, # 2, p. 419 - 428
[2] Patent: WO2018/15818, 2018, A2. Location in patent: Paragraph 00237
[3] Patent: WO2018/64135, 2018, A1. Location in patent: Paragraph 0275-0278
[4] Patent: US2011/65700, 2011, A1. Location in patent: Page/Page column 17
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5138 - 5145

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