Showing Compound Card for Benzonitrile (CDB000563)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:43:55 UTC
Updated at2020-11-18 16:35:16 UTC
CannabisDB IDCDB000563
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzonitrile
DescriptionBenzonitrile, also known as cyanobenzene or phenyl cyanide, belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine. Benzonitrile is a rancid tasting compound and it has been detected, but not quantified, in a few different foods, such as cherry and garden tomato. Benzonitrile is a potentially toxic compound to humans. Benzonitrile is a useful solvent and a versatile precursor to many derivatives such as benzamides and Diphenylketimine. It is produced by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F) (doi:10.1002/14356007.a03_555). Benzonitrile has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ) and is a constituent of marijuana smoke ( Ref:DOI ). Benzonitrile is volatilized during the combustion of cannabis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BenzenenitrileChEBI
Benzoic acid nitrileChEBI
C6H5-CNChEBI
CyanobenzeneChEBI
Phenyl cyanideChEBI
Benzoate nitrileGenerator
Chemical FormulaC7H5N
Average Molecular Weight103.12
Monoisotopic Molecular Weight103.0422
IUPAC Namebenzonitrile
Traditional Namebenzonitrile
CAS Registry Number100-47-0
SMILES
N#CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
InChI KeyJFDZBHWFFUWGJE-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzonitriles
Direct ParentBenzonitriles
Alternative Parents
Substituents
  • Benzonitrile
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point−13 °CWikipedia
Boiling Point188 to 191 °CWikipedia
Water Solubility0 g/100 mL at 22 °CWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.55ALOGPS
logP1.83ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.78 m³·mol⁻¹ChemAxon
Polarizability10.83 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)splash10-0udi-9800000000-d5c0241728a7745a77022014-09-20View Spectrum
GC-MSBenzonitrile, non-derivatized, GC-MS Spectrumsplash10-0udi-8900000000-cdfb666a4d4749562a5cSpectrum
GC-MSBenzonitrile, non-derivatized, GC-MS Spectrumsplash10-003s-9000000000-06fca1d207820656ef9aSpectrum
GC-MSBenzonitrile, non-derivatized, GC-MS Spectrumsplash10-0ufr-9700000000-8050afa6cc9ac952013bSpectrum
GC-MSBenzonitrile, non-derivatized, GC-MS Spectrumsplash10-0udi-3900000000-b00c11fc42a8a2563124Spectrum
GC-MSBenzonitrile, non-derivatized, GC-MS Spectrumsplash10-0udi-9300000000-1a24ace18d57f2a6713bSpectrum
Predicted GC-MSBenzonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-5900000000-1ff23906521d255176e0Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-9000000000-6ac90d455cfdec9115d82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-0900000000-d4c7faab0f209a8c68682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-0900000000-d061e3e41fc5107b47842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-0900000000-c9d7c714bcf4f5579ef32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-0900000000-3bc83aa336bbe0a8257e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-2900000000-aa9b10960fb2a03111f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0udi-4900000000-e16f8bb3ab535d3b789c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fb9-9800000000-7f2b946f7845f493e5092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-004i-9200000000-e7d5990807c1201b28962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-004i-9000000000-695edf453363a989236b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-0900000000-d4c7faab0f209a8c68682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-0900000000-d4c7faab0f209a8c68682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-0900000000-d4c7faab0f209a8c68682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-0900000000-d4c7faab0f209a8c68682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-0900000000-74a1a056fd484876efd22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0udi-3900000000-791150ed0a88f94083882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0ufr-7900000000-6f7f76ee17b8d8954eaa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-004i-9000000000-4a8521698aeff106f7ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-004i-9000000000-f9f30a66e3bafd25e8e22017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-bb01802d46102f9d59a42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6ac03bb6e19f3dd5223b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7900000000-286e50d353aa02c699b72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-786ecf8ab3f999b67a712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-786ecf8ab3f999b67a712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4900000000-3133a956d40baf5f16672016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0062085
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029710
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC09814
BioCyc IDCPD-15582
BiGG IDNot Available
Wikipedia LinkBenzonitrile
METLIN IDNot Available
PubChem Compound7505
PDB IDNot Available
ChEBI ID27991
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 ]