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475039-81-7

475039-81-7 Structure

475039-81-7 Structure
IdentificationBack Directory
[Name]

4-Bromo-3-methyl-indole
[CAS]

475039-81-7
[Synonyms]

4-Bromo-3-methyl-indole
4-bromo-3-methyl-1H-indole
1H-INDOLE,4-BROMO-3-METHYL-
[Molecular Formula]

C9H8BrN
[MDL Number]

MFCD15144591
[MOL File]

475039-81-7.mol
[Molecular Weight]

210.07
Chemical PropertiesBack Directory
[Melting point ]

ca. 25-30℃
[Boiling point ]

325.1±22.0 °C(Predicted)
[density ]

1.563±0.06 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[form ]

powder
[pka]

16.37±0.30(Predicted)
[color ]

White
[Sensitive ]

Light Sensitive
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

4-Bromo-3-methyl-indole(475039-81-7)1HNMR
Hazard InformationBack Directory
[Synthesis]

4-Bromoindole-3-carboxaldehyde

98600-34-1

4-Bromo-3-methyl-indole

475039-81-7

General procedure for the synthesis of 4-bromo-3-methyl-1H-indole from 4-bromoindole-3-carboxaldehyde: Lithium aluminum hydride (LAH, 1.0 M tetrahydrofuran (THF) solution, 5.75 mL, 5.75 mmol) was added slowly and dropwise to refluxed 4-bromo-1H-indole-3-carboxaldehyde (644 mg, 2.87 mmol) in anhydrous THF (20 mL); Intermediate 27) solution. The reaction mixture was refluxed for 1 h and cooled to room temperature. The reaction was quenched sequentially by the addition of water (220 μL), 15% aqueous sodium hydroxide solution (220 μL) and water (650 μL). The resulting precipitate was collected by filtration, the filtrate was concentrated, and the residue was extracted with aqueous sodium hydroxide (10 mL) and dichloromethane (2 x 10 mL). The organic layer was combined with a previous batch (from 4-bromo-1H-indole-3-carboxaldehyde, 100 mg, 0.45 mmol; starting with Intermediate 27) of this intermediate, dried and concentrated to give the title compound (556 mg, 80% yield) as a light brown oil. Mass spectrometry (ESI+) analysis showed the molecular ion peak m/z 210 (M+H)+ for C9H8BrN.

[References]

[1] Patent: WO2008/3703, 2008, A1. Location in patent: Page/Page column 85-86
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 160
[3] Patent: WO2013/16197, 2013, A1. Location in patent: Page/Page column 80-81
[4] Patent: WO2015/66344, 2015, A1. Location in patent: Page/Page column 223
[5] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
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