Benzofuran (CHEM003170)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:53:12 UTC
Update Date2026-04-17 16:29:48 UTC
Accession NumberCHEM003170
Identification
Common NameBenzofuran
ClassSmall Molecule
DescriptionBenzofuran is found in alcoholic beverages. Benzofuran is maillard produced present in roasted coffee aroma. Benzofuran is a constituent of Coix lachryma-jobi (Job's tears) and Gentiana lutea (yellow gentian) Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. It is the parent of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofuran has been shown to exhibit anti-microbial function (1).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Benzo[b]furanChEBI
CoumaronChEBI
CoumaroneChEBI
CumaroneChEBI
1-BenzofuranHMDB
1-OxaindeneHMDB
1-OxideneHMDB
1-OxindeneHMDB
2,3-BenzofuranHMDB, MeSH
benzo(b)FuranHMDB, MeSH
BenzofurfuranHMDB, MeSH
BZFHMDB
CumaronHMDB
BenzofuranChEBI
Chemical FormulaC8H6O
Average Molecular Mass118.133 g/mol
Monoisotopic Mass118.042 g/mol
CAS Registry Number271-89-6
IUPAC Name1-benzofuran
Traditional Namebenzofuran
SMILESO1C=CC2=C1C=CC=C2
InChI IdentifierInChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChI KeyIANQTJSKSUMEQM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< -18°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.75ALOGPS
logP2.13ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.9 m³·mol⁻¹ChemAxon
Polarizability12.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9500000000-3d2e5f26beb578276710Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9500000000-3d2e5f26beb578276710Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-efdcea5ed8b525799ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-bb3695060acd0d637949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7900000000-9b6327284d187ad5caacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-20b4b4e88a2b2a09c04eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-f6b69baead38b400da70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9600000000-9853e0fb4ec328aab100Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-86dbc8125a6459f35443Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-86dbc8125a6459f35443Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-86dbc8125a6459f35443Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-2c459a5a01556d862777Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-d4accbc7d32bf7e04587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9000000000-5c6f3768e856876b51efSpectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9700000000-e2e60a740f22f28eaf54Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04179
HMDB IDHMDB0032929
FooDB IDFDB010914
Phenol Explorer IDNot Available
KNApSAcK IDC00054105
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1-benzofuran
Chemspider ID8868
ChEBI ID35260
PubChem Compound ID9223
Kegg Compound IDC14512
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Wilhelm Kaupmann, Klaus-Wolf VON Eickstedt, Salah-Eldin Rahman, “Amino carbonyl derivatives of benzofurans, processes for their production, and pharmaceutical compositions containing the same 2-phenyl-3-[3-dialkylaminopropanoyl]benzofuran compounds.” U.S. Patent US4009184, issued October, 1968.

MSDSNot Available
General References
1. Wahab Khan M, Jahangir Alam M, Rashid MA, Chowdhury R: A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem. 2005 Aug 15;13(16):4796-805.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.