2-(4-broMophenyl)propanenitrile

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2-(4-broMophenyl)propanenitrile Basic information
Product Name:2-(4-broMophenyl)propanenitrile
Synonyms:2-(4-broMophenyl)propanenitrile;2-(4-BroMo-phenyl)-propionitrile;Benzeneacetonitrile, 4-bromo-α-methyl-
CAS:42186-06-1
MF:C9H8BrN
MW:210.07
EINECS:
Product Categories:
Mol File:42186-06-1.mol
2-(4-broMophenyl)propanenitrile Structure
2-(4-broMophenyl)propanenitrile Chemical Properties
Boiling point 293.3±15.0 °C(Predicted)
density 1.409±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
Appearancecolorless to light yellow liquid
Safety Information
MSDS Information
2-(4-broMophenyl)propanenitrile Usage And Synthesis
Synthesis Reference(s)The Journal of Organic Chemistry, 42, p. 3114, 1977 DOI: 10.1021/jo00439a002
Synthesis
4-Bromophenylacetonitrile

16532-79-9

Iodomethane

74-88-4

2-(4-broMophenyl)propanenitrile

42186-06-1

Example 649 Synthesis of 2-(4-bromophenyl)propionitrile: 2-(4-bromophenyl)acetonitrile (5.0 g, 25.5 mmol) was dissolved in anhydrous THF (70 mL) and cooled to 0°C. Sodium hydride (60 wt%, 1.5 g, 38.3 mmol) was added batchwise under stirring. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, methyl iodide (1.8 mL, 28.1 mmol) was added and stirring was continued for 14 hours. Upon completion of the reaction, the reaction was carefully quenched with water at 0 °C and diluted with ethyl acetate (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, 0-30% ethyl acetate/heptane gradient elution) to afford the target product, 2-(4-bromophenyl)propionitrile (3.8 g, 72%), as a yellow oil.ESI MS m/z 210 [C9H8BrN + H]+.

References[1] Journal of the American Chemical Society, 2015, vol. 137, # 19, p. 6156 - 6159
[2] Patent: WO2011/123419, 2011, A1. Location in patent: Page/Page column 386
[3] Patent: WO2017/139778, 2017, A1. Location in patent: Paragraph 00487
[4] Patent: US2013/331375, 2013, A1. Location in patent: Paragraph 0178
[5] Patent: WO2018/140876, 2018, A1. Location in patent: Page/Page column 113; 115
2-(4-broMophenyl)propanenitrile Preparation Products And Raw materials
Raw materials4-Bromophenylacetonitrile-->Iodomethane-->Tetrahydrofuran-->Sodium hydride
Preparation Products2-(4-broMophenyl)propan-1-aMine
Tag:2-(4-broMophenyl)propanenitrile(42186-06-1) Related Product Information
2-(4-broMophenyl)propanoic acid 2-(4-Bromophenyl)-2-methylpropanenitrile 4-Bromophenylacetonitrile 2-(4-Bromophenyl)propanamide Benzeneacetic acid, 4-bromo-α-methyl-, (αR)- (S)-2-(4-bromophenyl)propanoic acid