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1192004-62-8

1192004-62-8 Structure

1192004-62-8 Structure
IdentificationBack Directory
[Name]

4-broMo-5-Methoxy-1H-indazole
[CAS]

1192004-62-8
[Synonyms]

4-broMo-5-Methoxy-1H-indazole
1H-Indazole, 4-bromo-5-methoxy-
[Molecular Formula]

C8H7BrN2O
[MDL Number]

MFCD17676852
[MOL File]

1192004-62-8.mol
[Molecular Weight]

227.06
Chemical PropertiesBack Directory
[Boiling point ]

363.4±22.0 °C(Predicted)
[density ]

1.678±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

12.39±0.40(Predicted)
[Appearance]

Light yellow to yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

4-broMo-5-Methoxy-1H-indazole(1192004-62-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

3-broMo-4-Methoxy-2-Methylaniline

29237-10-3

4-broMo-5-Methoxy-1H-indazole

1192004-62-8

General procedure for the synthesis of 4-bromo-5-methoxy-1H-indazole from 3-bromo-4-methoxy-2-methylaniline: 1. 3-Bromo-4-methoxy-2-methylaniline (19.06 g) was dissolved in acetonitrile (250 mL), acetic anhydride (18.9 mL) was added slowly, and the reaction mixture was stirred for 1 hour at room temperature. 2. Potassium acetate (2.60 g) and amyl nitrite (22.3 g) were added to the reaction mixture and heated to reflux for 8 hours. 3. After completion of the reaction, the reaction mixture was concentrated and 6 M hydrochloric acid (200 mL) was added to the residue and heated to reflux overnight. 4. The reaction mixture was neutralized with 8 M sodium hydroxide and subsequently extracted with ethyl acetate. 5. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. 6. The residue was dissolved in tetrahydrofuran, treated with activated charcoal, filtered to remove the activated charcoal and the filtrate was concentrated. 7. The residue was crystallized with diisopropyl ether, the crystals were collected by filtration, washed with diisopropyl ether and dried to obtain the target compound 4-bromo-5-methoxy-1H-indazole (10.42 g, yield 52%) as yellow crystals. Melting point: 178-180°C. Mass spectrum (MS): 229 (MH+).

[References]

[1] Patent: EP2266983, 2010, A1. Location in patent: Page/Page column 48
[2] Patent: US2009/286800, 2009, A1. Location in patent: Page/Page column 109; 111
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