ContaminantDB: Benzonitrile

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 19:45:57 UTC

Accession Number

CHEM001447

Identification

Common Name

Benzonitrile

Class

Small Molecule

Description

Benzonitrile is a chemical compound of cyanide. It is a useful solvent and a versatile precursor to many derivatives, thus it is often used in organic chemistry. (3)

Contaminant Sources

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

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzenenitrile	ChEBI
Benzoic acid nitrile	ChEBI
C6H5-CN	ChEBI
Cyanobenzene	ChEBI
Phenyl cyanide	ChEBI
Benzoate nitrile	Generator

Chemical Formula

C₇H₅N

Average Molecular Mass

103.121 g/mol

Monoisotopic Mass

103.042 g/mol

CAS Registry Number

100-47-0

IUPAC Name

benzonitrile

Traditional Name

benzonitrile

SMILES

N#CC1=CC=CC=C1

InChI Identifier

InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H

InChI Key

JFDZBHWFFUWGJE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzonitriles

Direct Parent

Benzonitriles

Alternative Parents

Substituents

Benzonitrile
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:27991 )
benzenes (CHEBI:27991 )

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

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-12.7°C
Boiling Point	Not Available
Solubility	2 mg/mL at 25°C [RIDDICK,JA et al. (1986)]

Predicted Properties

Property	Value	Source
Water Solubility	9.25 g/L	ALOGPS
logP	1.55	ALOGPS
logP	1.83	ChemAxon
logS	-1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.78 m³·mol⁻¹	ChemAxon
Polarizability	10.83 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)	splash10-0udi-8900000000-cdfb666a4d4749562a5c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003s-9000000000-06fca1d207820656ef9a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-9700000000-8050afa6cc9ac952013b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-3900000000-b00c11fc42a8a2563124	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-9300000000-1a24ace18d57f2a6713b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5900000000-1ff23906521d255176e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00di-9000000000-6ac90d455cfdec9115d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-0900000000-d4c7faab0f209a8c6868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-0900000000-d061e3e41fc5107b4784	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-0900000000-c9d7c714bcf4f5579ef3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-0900000000-3bc83aa336bbe0a8257e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-2900000000-aa9b10960fb2a03111f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0udi-4900000000-e16f8bb3ab535d3b789c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0fb9-9800000000-7f2b946f7845f493e509	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-004i-9200000000-e7d5990807c1201b2896	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-004i-9000000000-695edf453363a989236b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-0900000000-d4c7faab0f209a8c6868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-0900000000-d4c7faab0f209a8c6868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-0900000000-d4c7faab0f209a8c6868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-0900000000-d4c7faab0f209a8c6868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-0900000000-74a1a056fd484876efd2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0udi-3900000000-791150ed0a88f9408388	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0ufr-7900000000-6f7f76ee17b8d8954eaa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-004i-9000000000-4a8521698aeff106f7ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-004i-9000000000-f9f30a66e3bafd25e8e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-bb01802d46102f9d59a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-6ac03bb6e19f3dd5223b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-7900000000-286e50d353aa02c699b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-786ecf8ab3f999b67a71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-786ecf8ab3f999b67a71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-4900000000-3133a956d40baf5f1667	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-9800000000-d5c0241728a7745a7702	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

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. (2)

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. (1)

Toxicity Values

LD50: 971 mg/kg (Oral, Rat) (4) LD50: 740 mg/kg (Intraperitoneal, Rat) (4) LD50: 180 mg/kg (Subcutaneous, Mouse) (4) LD50: 1200 mg/kg (Dermal, Rat) (6)

Lethal Dose

207 to 300 milligrams for an adult human (cyanide salts). (5)

Carcinogenicity (IARC Classification)

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

Uses/Sources

Benzonitrile is a useful solvent and a versatile precursor to many derivatives, thus it is often used in organic chemistry. (3)

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. (1, 2)

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. (1, 2)

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. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0062085

FooDB ID

FDB029710

Phenol Explorer ID

Not Available

KNApSAcK ID