3-PHENYLPROPIONITRILE Property

Melting point:

−2-−1 °C(lit.)

Boiling point:

113 °C9 mm Hg(lit.)

Density 

1.001 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.521(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

1.68g/l (calculated)

form 

Liquid

Specific Gravity

1

color 

Clear colorless to light yellow

Odor

powerful nasturtium

BRN 

636348

Exposure limits

NIOSH: IDLH 25 mg/m3

CAS DataBase Reference

645-59-0(CAS DataBase Reference)

EPA Substance Registry System

Benzenepropanenitrile (645-59-0)

Safety

Hazard Codes 

T,C

Risk Statements 

23/24/25-36-34

Safety Statements 

36/37/39-45-27-26

RIDADR 

UN 3276 6.1/PG 3

WGK Germany 

3

RTECS 

MW5604750

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29269095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

3-PHENYLPROPIONITRILE Chemical Properties,Usage,Production

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.

Definition

ChEBI: A nitrile that is propionitrile in which one of the methyl hydrogens has been replaced by a phenyl group.

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).

Synthesis Reference(s)

Journal of the American Chemical Society, 98, p. 4685, 1976 DOI: 10.1021/ja00431a078
Chemical 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.