3-Fluoro-4-Bromoobenzyl Cyanide Chemical Properties

Boiling point:

279℃

Density 

1.573

Flash point:

122℃

storage temp. 

2-8°C

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C8H5BrFN/c9-7-2-1-6(3-4-11)5-8(7)10/h1-2,5H,3H2

InChIKey

CGDCFGJXTOGEGD-UHFFFAOYSA-N

SMILES

C1(CC#N)=CC=C(Br)C(F)=C1

Safety Information

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2926907090

3-Fluoro-4-Bromoobenzyl Cyanide Usage And Synthesis

Uses

3-Fluoro-4-bromophenylacetonitrile is a commonly used chemical intermediate, prepared by cyanidation.

Chemical Properties

Off-white powder

Synthesis

A mixture of 3-fluoro-4-bromobenzyl bromide (27 mmol) and sodium cyanide (2.38 g, 54 mmol, 2.0 eq.) in ethanol (100 mL) was heated and reacted at 80 °C for 2 hours. Upon completion of the reaction, the mixture was concentrated to dryness under vacuum, followed by suspension of the residue in water and extraction with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product as a heavy oil. Purification by silica gel column chromatography (eluent gradient: 2%→12% ethyl acetate/hexane) resulted in 3-fluoro-4-bromophenylacetonitrile as white acicular crystals (1.96 g, 35% overall yield in two steps).

References

[1] Patent: WO2011/15287, 2011, A2. Location in patent: Page/Page column 13; 14
[2] Patent: US2011/39934, 2011, A1. Location in patent: Page/Page column 5
[3] Patent: EP2700643, 2014, A1. Location in patent: Paragraph 0235
[4] Patent: US2015/368278, 2015, A1. Location in patent: Paragraph 1263
[5] Patent: WO2017/98440, 2017, A1. Location in patent: Page/Page column 184

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