Showing Compound Benzeneacetonitrile (FDB012457)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2020-09-17 15:34:49 UTC

Primary ID

FDB012457

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Benzeneacetonitrile

Description

Benzyl nitrile or Benzeneacetonitrile, also known as benzyl cyanide or alpha-cyanotoluene, belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. Benzeneacetonitrile is found, on average, in the highest concentration within kohlrabis and peppermints. Benzeneacetonitrile has also been detected, but not quantified, in several different foods, such as cabbages, cauliflowers, garden and cherry tomato. Benzeneacetonitrile has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Benzeneacetonitrile is a potentially toxic compound. Benzyl nitrile is a colorless oily aromatic liquid and an important precursor to numerous compounds in organic chemistry. Benzyl nitrile is a useful precursor to numerous drugs with recreational use potential. Benzyl nitrile can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.

CAS Number

140-29-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(Cyanomethyl)benzene	ChEBI
2-Phenylacetonitrile	ChEBI
alpha-Cyanotoluene	ChEBI
alpha-Tolunitrile	ChEBI
Benzyl cyanide	ChEBI
Benzyl nitrile	ChEBI
a-Cyanotoluene	Generator
Α-cyanotoluene	Generator
a-Tolunitrile	Generator
Α-tolunitrile	Generator
.omega.-cyanotoluene	HMDB
Acetic acid, phenyl-nitrile	HMDB
alpha -Cyanotoluene	HMDB
alpha -Tolunitrile	HMDB
alpha-cyano-Toluene	HMDB
Benzeneacetonitrile, 9ci	HMDB
Benzylkyanid	HMDB
Benzylnitrile	HMDB
Cyanophenylmethane	HMDB
Enzylcyanide	HMDB
laquo omegaraquo -Cyanotoluene	HMDB
Omega-cyanotoluene	HMDB
Phenacetonitrile	HMDB
Phenyl acetyl nitrile	HMDB
Phenyl-acetonitrile	HMDB
Phenylacetonitrile	HMDB
Phenylacetonitrile, liquid	HMDB
Benzeneacetonitrile	ChEBI
α-cyano-	biospider
α-cyanotoluene	biospider
α-tolunitrile	biospider
«omega»-cyanotoluene	biospider
Acetonitrile, phenyl-	biospider
alpha-Cyano-toluene	HMDB
Alpha-cyanotoluene	biospider
Alpha-tolunitrile	biospider
Benzeneacetonitrile, 9CI	db_source
Laquo omegaraquo -cyanotoluene	HMDB
Phenylacetonitrile, liquid [UN2470] [Poison]	biospider
Toluene, α-cyano-	biospider
Toluene, alpha-cyano-	biospider
α-cyanotoluene	Generator
α-tolunitrile	Generator

Predicted Properties

Property	Value	Source
Water Solubility	6.85 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.67	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.34 m³·mol⁻¹	ChemAxon
Polarizability	12.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H7N

IUPAC name

2-phenylacetonitrile

InChI Identifier

InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2

InChI Key

SUSQOBVLVYHIEX-UHFFFAOYSA-N

Isomeric SMILES

N#CCC1=CC=CC=C1

Average Molecular Weight

117.1479

Monoisotopic Molecular Weight

117.057849229

Classification

Description

Belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl cyanides

Direct Parent

Benzyl cyanides

Alternative Parents

Substituents

Benzyl-cyanide
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:25979 )
benzenes (CHEBI:25979 )
a small molecule (PHENYLACETONITRILE )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Respiratory, thoracic and mediastinal disorders:

Apnea

Nervous system disorders:

Seizure

Psychiatric disorders:

Confusion

Ear and labyrinth disorders:

Vertigo

General disorders and administration site conditions:

Pain

Cardiac disorders:

Cardiac arrest

Gastrointestinal disorders:

Vomiting

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Environmental role:

Air pollutant

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 82.02%; H 6.02%; N 11.96%	DFC
Melting Point	-23.8 oC
Boiling Point	Bp12 107°	DFC
Experimental Water Solubility	0.1 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP	1.56	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d1515 1.02	DFC
Refractive Index	n25D 1.5211	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014i-9600000000-bacbbfee69800587e876	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-9700000000-aa951610ae3086079fc3	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-6900000000-9fa568274538519d6221	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-4900000000-7fb420e2a4693843bcc6	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-9700000000-44dc07c52f713661d49d	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-9700000000-aa951610ae3086079fc3	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-6900000000-9fa568274538519d6221	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-4900000000-7fb420e2a4693843bcc6	Spectrum
GC-MS	Benzeneacetonitrile, non-derivatized, GC-MS Spectrum	splash10-014i-9700000000-44dc07c52f713661d49d	Spectrum
Predicted GC-MS	Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-9600000000-3ff8c2a019af8041ccf5	Spectrum
Predicted GC-MS	Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-26618186da25d2fb36a3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-36bcc9666d8d6f02be93	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-e64aaf4670bfdd42e5ec	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-c300e5c9a5a8fd9efed7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-62ae29742c669f0cbb48	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-9400000000-a31fa80a0b41e8872dfd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-89c3f30c8225ba6d5d62	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-89c3f30c8225ba6d5d62	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-7900000000-a5d53547c4ff1f8c5b08	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9600000000-37eae74477faef6aa26e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-0ed055b02df43a8a2055	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-c6037f271472539420c4	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum