Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2020-09-17 15:34:49 UTC
Primary IDFDB012457
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzeneacetonitrile
DescriptionBenzyl 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 Number140-29-4
Structure
Thumb
Synonyms
SynonymSource
(Cyanomethyl)benzeneChEBI
2-PhenylacetonitrileChEBI
alpha-CyanotolueneChEBI
alpha-TolunitrileChEBI
Benzyl cyanideChEBI
Benzyl nitrileChEBI
a-CyanotolueneGenerator
Α-cyanotolueneGenerator
a-TolunitrileGenerator
Α-tolunitrileGenerator
.omega.-cyanotolueneHMDB
Acetic acid, phenyl-nitrileHMDB
alpha -CyanotolueneHMDB
alpha -TolunitrileHMDB
alpha-cyano-TolueneHMDB
Benzeneacetonitrile, 9ciHMDB
BenzylkyanidHMDB
BenzylnitrileHMDB
CyanophenylmethaneHMDB
EnzylcyanideHMDB
laquo omegaraquo -CyanotolueneHMDB
Omega-cyanotolueneHMDB
PhenacetonitrileHMDB
Phenyl acetyl nitrileHMDB
Phenyl-acetonitrileHMDB
PhenylacetonitrileHMDB
Phenylacetonitrile, liquidHMDB
BenzeneacetonitrileChEBI
α-cyano-biospider
α-cyanotoluenebiospider
α-tolunitrilebiospider
«omega»-cyanotoluenebiospider
Acetonitrile, phenyl-biospider
alpha-Cyano-tolueneHMDB
Alpha-cyanotoluenebiospider
Alpha-tolunitrilebiospider
Benzeneacetonitrile, 9CIdb_source
Laquo omegaraquo -cyanotolueneHMDB
Phenylacetonitrile, liquid [UN2470] [Poison]biospider
Toluene, α-cyano-biospider
Toluene, alpha-cyano-biospider
α-cyanotolueneGenerator
α-tolunitrileGenerator
Predicted Properties
PropertyValueSource
Water Solubility6.85 g/LALOGPS
logP1.42ALOGPS
logP1.67ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.34 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H7N
IUPAC name2-phenylacetonitrile
InChI IdentifierInChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeySUSQOBVLVYHIEX-UHFFFAOYSA-N
Isomeric SMILESN#CCC1=CC=CC=C1
Average Molecular Weight117.1479
Monoisotopic Molecular Weight117.057849229
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl cyanides
Direct ParentBenzyl cyanides
Alternative Parents
Substituents
  • Benzyl-cyanide
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 82.02%; H 6.02%; N 11.96%DFC
Melting Point-23.8 oC
Boiling PointBp12 107°DFC
Experimental Water Solubility0.1 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP1.56HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd1515 1.02DFC
Refractive Indexn25D 1.5211DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9600000000-bacbbfee69800587e876Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-aa951610ae3086079fc3Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-6900000000-9fa568274538519d6221Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-7fb420e2a4693843bcc6Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-44dc07c52f713661d49dSpectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-aa951610ae3086079fc3Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-6900000000-9fa568274538519d6221Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-7fb420e2a4693843bcc6Spectrum
GC-MSBenzeneacetonitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-44dc07c52f713661d49dSpectrum
Predicted GC-MSBenzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9600000000-3ff8c2a019af8041ccf5Spectrum
Predicted GC-MSBenzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-26618186da25d2fb36a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-36bcc9666d8d6f02be93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-e64aaf4670bfdd42e5ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c300e5c9a5a8fd9efed7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-62ae29742c669f0cbb48Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9400000000-a31fa80a0b41e8872dfdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-89c3f30c8225ba6d5d62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-89c3f30c8225ba6d5d62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-7900000000-a5d53547c4ff1f8c5b08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9600000000-37eae74477faef6aa26eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-0ed055b02df43a8a2055Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c6037f271472539420c4Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID13839308
ChEMBL IDNot Available
KEGG Compound IDC16074
Pubchem Compound ID8794
Pubchem Substance IDNot Available
ChEBI ID25979
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34171
CRC / DFC (Dictionary of Food Compounds) IDFDG02-B:HHB12-D
EAFUS IDNot Available
Dr. Duke IDBENZYL-CYANIDE|PHENYLACETONITRILE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).