Phenylacetonitrile

Structural formula
General
Surname	Phenylacetonitrile
other names	Benzyl cyanide; α-tolunitrile;
Molecular formula	C 8 H 7 N
Brief description	colorless oily liquid with an aromatic odor
External identifiers / databases
EC number	205-410-5
ECHA InfoCard	100.004.919
PubChem	8794
Wikidata	Q425620
properties
Molar mass	117.15 g mol −1
Physical state	liquid
density	1.02 g cm −3
Melting point	−24 ° C
boiling point	234 ° C
Vapor pressure	0.07 h Pa (20 ° C)
solubility	heavy in water (0.1 g l −1 at 20 ° C)
Refractive index	1.5211 (25 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301 + 311-330
	P: 280-302 + 352-304 + 340-308 + 310
Toxicological data	270 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Phenylacetonitrile is a colorless (chemically pure, but mostly yellowish) liquid that is present at room temperature and is very toxic chemical compound.

Occurrence in nature

Desert locust ( Schistocerca gregaria )

In nature, phenylacetonitrile is found in garden cress. It is contained in the secretion of the desert locust and is used by insects as a fragrance ( pheromone ).

presentation

Phenylacetonitrile 2 can be synthesized by chlorination of toluene 1 to benzyl chloride and subsequent reaction with sodium cyanide in ethanol according to the Kolbe nitrile synthesis.

use

Phenylacetonitrile is used as an intermediate in the chemical industry and as a fragrance . The compound is the starting material for the production of phenylacetic acid .

Individual evidence

↑ ^a ^b ^c Entry on phenylacetonitrile. In: Römpp Online . Georg Thieme Verlag, accessed on June 15, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g Entry on phenylacetonitrile in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-32.
↑ Benzyl cyanide data sheet (PDF) from Merck , accessed on January 28, 2018.
↑ Ulrike Knoll: Behavioral research: scent spies . In: Spektrum.de, February 17, 2005, accessed on January 28, 2018.
^ S. Hauptmann, J. Gräfe, H. Remane: Textbook of Organic Chemistry, Deutscher Verlag der Grundstoffindustrie Leipzig 1980, p. 378.
^ Roger Adams, AF Thal: Benzyl Cyanide In: Organic Syntheses . 2, 1922, p. 9, doi : 10.15227 / orgsyn.002.0009 ; Coll. Vol. 1, 1941, p. 107 ( PDF ).

[Römpp-1] Entry on phenylacetonitrile. In: Römpp Online . Georg Thieme Verlag, accessed on June 15, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on phenylacetonitrile in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[CRC90_3_32-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-32.

[4] Benzyl cyanide data sheet (PDF) from Merck , accessed on January 28, 2018.

[5] Ulrike Knoll: Behavioral research: scent spies . In: Spektrum.de, February 17, 2005, accessed on January 28, 2018.

[6] S. Hauptmann, J. Gräfe, H. Remane: Textbook of Organic Chemistry, Deutscher Verlag der Grundstoffindustrie Leipzig 1980, p. 378.

[7] Roger Adams, AF Thal: Benzyl Cyanide In: Organic Syntheses . 2, 1922, p. 9, doi : 10.15227 / orgsyn.002.0009 ; Coll. Vol. 1, 1941, p. 107 ( PDF ).