1-(1H-Indazol-3-yl)ethanone

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1-(1H-Indazol-3-yl)ethanone Basic information
Product Name:1-(1H-Indazol-3-yl)ethanone
Synonyms:Ethanone, 1-(1H-indazol-3-yl)- (9CI);3-ACETYLINDAZOLE;1-(1H-Indazole-3-yl)ethanone;3-Acetyl-1H-indazole;1-(indazol-3-yl)ethan-1-one;Ethanone, 1-(1H-indazol-3-yl)-;3-Acetylindazole(WX626026);1-(1H-indazol-3-yl)ethan-1-one
CAS:4498-72-0
MF:C9H8N2O
MW:160.17
EINECS:
Product Categories:ACETYLGROUP
Mol File:4498-72-0.mol
1-(1H-Indazol-3-yl)ethanone Structure
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
pka11.87±0.40(Predicted)
AppearanceOff-white to light yellow Solid
Safety Information
Hazard Codes Xn
Risk Statements 22
MSDS Information
1-(1H-Indazol-3-yl)ethanone Usage And Synthesis
Synthesis Reference(s)Synthesis, p. 937, 1992 DOI: 10.1055/s-1992-26268
Synthesis
1H-INDAZOLE-3-(N-METHOXY-METHYL)CARBAMIDE

351457-12-0

Methylmagnesium Bromide

75-16-1

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

4498-72-0

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
1-(1H-Indazol-3-yl)ethanone Preparation Products And Raw materials
Raw materials1H-Indazole-3-(N-methoxy-methyl)carbamide-->Methylmagnesium Bromide
Tag:1-(1H-Indazol-3-yl)ethanone(4498-72-0) Related Product Information
4-Fluoro-1-methylindazole 1H-Indazole-7-carboxamide(9CI) 6-Bromo-1H-indazol-3-ol 5-Bromo-3-hydroxy (1H)indazole 3-Bromo-4-fluoro (1H)indazole 1-Methyl-5-nitro-1H-indazole 3-(1H-Indazol-3-yl)-3-oxo-propionic acid ethyl ester 1-(6-Methoxy-1H-indazol-3-yl)-ethanone 1-(1H-Indazol-3-yl)ethanone 1-(6-Methoxy-1H-indazol-3-yl)-2-methylpropan-1-one 3-Benzoyl-1-methyl-1H-naphtho[2,3-g]indazole-6,11-dione 3-(2-Oxo-2-phenylacetyl)-1H-naphtho[2,3-g]indazole-6,11-dione 3-Benzoyl-1H-naphtho[2,3-g]indazole-6,11-dione 1-(6-Methoxy-1H-indazol-3-yl)-propan-1-one (6-Methoxy-1H-indazol-3-yl)(phenyl)methanone 1H-Indazole-3-ylphenyl methanone SINOVA SL-02763 CHEMPACIFIC 39982