Showing Compound Card for Benzyl nitrile (CDB000568)

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Record Information
Version1.0
Created at2020-03-19 00:44:14 UTC
Updated at2020-12-07 19:07:32 UTC
CannabisDB IDCDB000568
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzyl nitrile
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 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC8H7N
Average Molecular Weight117.15
Monoisotopic Molecular Weight117.0578
IUPAC Name2-phenylacetonitrile
Traditional Namephenylacetonitrile
CAS Registry Number140-29-4
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 KeySUSQOBVLVYHIEX-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.
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-23.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 25 °CNot Available
logP1.56Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9600000000-bacbbfee69800587e8762014-09-20View Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-aa951610ae3086079fc3Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-6900000000-9fa568274538519d6221Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-7fb420e2a4693843bcc6Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-44dc07c52f713661d49dSpectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-aa951610ae3086079fc3Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-6900000000-9fa568274538519d6221Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-7fb420e2a4693843bcc6Spectrum
GC-MSBenzyl nitrile, non-derivatized, GC-MS Spectrumsplash10-014i-9700000000-44dc07c52f713661d49dSpectrum
Predicted GC-MSBenzyl nitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9600000000-3ff8c2a019af8041ccf5Spectrum
Predicted GC-MSBenzyl nitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzyl nitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-26618186da25d2fb36a32016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-36bcc9666d8d6f02be932016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-e64aaf4670bfdd42e5ec2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c300e5c9a5a8fd9efed72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-62ae29742c669f0cbb482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9400000000-a31fa80a0b41e8872dfd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-7900000000-a5d53547c4ff1f8c5b082021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9600000000-37eae74477faef6aa26e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-0ed055b02df43a8a20552021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c6037f271472539420c42021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034171
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012457
KNApSAcK IDC00007674
Chemspider ID13839308
KEGG Compound IDC16074
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8794
PDB IDNot Available
ChEBI ID25979
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]