ContaminantDB: Benzeneacetonitrile

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (39)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:27 UTC

Update Date

2026-03-31 18:10:08 UTC

Accession Number

CHEM001448

Identification

Common Name

Benzeneacetonitrile

Class

Small Molecule

Description

Benzeneacetonitrile is found in garden cress. Benzeneacetonitrile is isolated from oil of garden cress (Lepidium sativum) and other plant oils.

Contaminant Sources

Clean Air Act Chemicals
DEA Chemicals
FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cyanide Compound
Food Toxin
Industrial/Workplace Toxin
Metabolite
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₈H₇N

Average Molecular Mass

117.148 g/mol

Monoisotopic Mass

117.058 g/mol

CAS Registry Number

140-29-4

IUPAC Name

2-phenylacetonitrile

Traditional Name

phenylacetonitrile

SMILES

N#CCC1=CC=CC=C1

InChI Identifier

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

InChI Key

SUSQOBVLVYHIEX-UHFFFAOYSA-N

Chemical Taxonomy

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-23.8°C
Boiling Point	Not Available
Solubility	0.1 mg/mL at 25°C

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9700000000-aa951610ae3086079fc3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-9fa568274538519d6221	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-4900000000-7fb420e2a4693843bcc6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9700000000-44dc07c52f713661d49d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9700000000-aa951610ae3086079fc3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-6900000000-9fa568274538519d6221	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-4900000000-7fb420e2a4693843bcc6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9700000000-44dc07c52f713661d49d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9600000000-3ff8c2a019af8041ccf5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-26618186da25d2fb36a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-36bcc9666d8d6f02be93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-e64aaf4670bfdd42e5ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-c300e5c9a5a8fd9efed7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-62ae29742c669f0cbb48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-9400000000-a31fa80a0b41e8872dfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-89c3f30c8225ba6d5d62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-89c3f30c8225ba6d5d62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-7900000000-a5d53547c4ff1f8c5b08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9600000000-37eae74477faef6aa26e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-0ed055b02df43a8a2055	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-c6037f271472539420c4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-9600000000-bacbbfee69800587e876	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (10) ; inhalation (10) ; dermal (10)

Mechanism of Toxicity

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (11)

Metabolism

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (10)

Toxicity Values

LD50: 270 mg/kg (Dermal, Rabbit) (15) LD50: 10 mg/kg (Intraperitoneal, Mouse) (13) LD50: 45.5 mg/kg (Oral, Mouse) (13) LD50: 0.05 mg/L over 4 hours (Inhalation, Mouse) (15)

Lethal Dose

208 to 300 milligrams for an adult human (cyanide salts). (14)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Benzyl cyanide is an intermediate to the production of phenobarbital, methylphenidate, and many amphetamines. (12)

Minimum Risk Level

Not Available

Health Effects

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (10, 11)

Symptoms

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (10, 11)

Treatment

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (11)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034171

FooDB ID

FDB012457

Phenol Explorer ID

Not Available

KNApSAcK ID