Record Information
Version1.0
Creation date2011-09-21 00:05:07 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021917
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetrahydrofuran
DescriptionTetrahydrofuran (THF) is a contaminant of exposure and appears in human biofluids. The Food and Drug Administration (FDA) has announced recommendations to revise the permitted daily exposures for THF, and so has the International Conference on Harmonisation. THF oxidizes readily, which can lead to instability and result in cytotoxicity. It is a colourless low-viscosity liquid with a smell similar to diethyl ether and is one of the most polar ethers. Tetrahydrofuran is essentially considered in occupational toxicology, and acute poisoning cases are extremely rare. THF is often used for hydroborations used to synthesize primary alcohols. THF is often used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides). THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF tends to form peroxides on storage in air. (wikipedia, PMID: 16999122, 12742700, 14619948) [HMDB]
CAS Number109-99-9
Structure
Thumb
Synonyms
SynonymSource
1,4-EpoxybutaneChEBI
Butane alpha,delta-oxideChEBI
Butylene oxideChEBI
FuranidineChEBI
Tetramethylene oxideChEBI
THFChEBI
Butane a,delta-oxideGenerator
Butane α,δ-oxideGenerator
Butane a,δ-oxideHMDB
1,4-Epoxy-butaneHMDB
Butane a,D-oxideHMDB
CyclotetramethyleneHMDB
Cyclotetramethylene oxideHMDB
Diethylene oxideHMDB
HydrofuranHMDB
OxacyclopentaneHMDB
OxolaneHMDB
PolytetrahydrofuranHMDB
TetrahydrofuraanHMDB
TetrahydrofuraneHMDB
TetrahydrofuranneHMDB
TetraidrofuranoHMDB
TetrahydrofuranChEBI
1,4-epoxy-butanehmdb
Butane a,d-oxidehmdb
THF?manual
Predicted Properties
PropertyValueSource
Water Solubility69.7 g/LALOGPS
logP0.35ALOGPS
logP0.53ChemAxon
logS-0.01ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.55 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H8O
IUPAC nameoxolane
InChI IdentifierInChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
InChI KeyWYURNTSHIVDZCO-UHFFFAOYSA-N
Isomeric SMILESC1CCOC1
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
Classification
Description Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
GC-MSTetrahydrofuran, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
Predicted GC-MSTetrahydrofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9000000000-3a492c8c5b590a04fe86Spectrum
Predicted GC-MSTetrahydrofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-66253634d3f27573c6e6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0abc-9000000000-49362212e0db0e39a608Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-f307a5446840a5333e4fSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-15e25f01aff47ab7faccSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-5fecd52ae1047ea6ca80Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-a72cdfa78bc1624af6eeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-57b4553c011e61c13302Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-633756c4cb26edc87875Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-f7f21b58e32e3bbdc8e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3191fdff289240be2d93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-53ae58b025cd88229a02Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-e2c11950e59178898ca9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-6f602d2adfd99a361876Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-db869489a53547fd0e9aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-e32b752db8542e7e4c7eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-41ba71baeb0e935332bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-4ffb3617277fb64e8592Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-4e009d20cbcc725a95e3Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID7737
ChEMBL IDCHEMBL276521
KEGG Compound IDNot Available
Pubchem Compound ID8028
Pubchem Substance IDNot Available
ChEBI ID26911
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00246
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDFU1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTetrahydrofuran
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference