Chemical Properties
clear colorless to light yellow liquid
Uses
3-Phenylpropionitrile was used to study the free enzyme activity of nitrilase AtNIT1.
Uses
A glucosinolate enzymic hydrolosis product with potential antibacterial activities against plant pathogenic bacteria. 3-Phenylpropionitrile is occasionally used in
perfume compositions, mainly as a minor
ingredient in artificial flower absolutes, etc. The material can also be used in certain
types of exotic or very heavy floral fragrance,
e. g. Stephanotis, Pikake, Keora, Ginger Lily,
Tiare, Coffee flower, etc. Its warm and piquant, vegetable pungency
is utilized in flavor compositions for seasonings, etc. and in various spice blends. Normal use concentration is equivalent to
about 1 to 3 ppm in the finished product.
Preparation
To a stirred solution of 3-phenylpropanamide (50 mg, 0.34 mmol) in acetonitrile (0.8 mL) at room temperature were successively added formic acid (0.2 mL) and paraformaldehyde (50 mg, 1.67 mmol). The reaction mixture was then refluxed for 12 h, and the solution obtained was cooled to room temperature.
Work-up A: The crude mixture was concentrated under reduced pressure, and the residue was subjected to flash chromatography on silica gel (230–240 mesh) eluting with hexane/ethyl acetate (7:3) to yield 3-phenylpropanonitrile (37 mg, 85%).
Work-up B: The reaction mixture was diluted with ethyl acetate (10 mL) and washed successively with saturated sodium hydrogen carbonate solution (5 mL) and water (5 mL). The combined aqueous layers were extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude 3-phenylpropanonitrile was purified as described above (Work-up A).
Definition
ChEBI: A nitrile that is propionitrile in which one of the methyl hydrogens has been replaced by a phenyl group.
Synthesis Reference(s)
Journal of the American Chemical Society, 98, p. 4685, 1976
DOI: 10.1021/ja00431a078Chemical and Pharmaceutical Bulletin, 10, p. 427, 1962
DOI: 10.1248/cpb.10.427
General Description
The effect of 3-Phenylpropionitrile on the growth and survival of woodlouse Porcellio scaber has been studied.
