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Showing Compound Benzenethiol (FDB011878)

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2015-07-20 22:44:17 UTC
Primary IDFDB011878
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzenethiol
DescriptionFlavouring agent Thiophenol is a chemical compound with the formula C6H5SH, and sometimes abbreviated as PhSH. The foul-smelling liquid is the principal aromatic thiol. The chemical structures of thiophenols are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, thio- commonly means that the oxygen atom is replaced by a sulfur atom.; Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in medicine merthiolate is a thiophenol.
CAS Number108-98-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
MercaptobenzeneChEBI
Phenyl mercaptanChEBI
PhenylthiolChEBI
FEMA 3616HMDB
mercapto-BenzeneHMDB
PhenylmercaptanHMDB
Sodium benzenethiolateHMDB
thio-PhenolHMDB
ThiofenolHMDB
ThiophenateHMDB, MeSH
ThiophenolHMDB, MeSH
Thiophenol, potassium saltMeSH, HMDB
Thiophenol, sodium saltMeSH, HMDB
Thiophenol, copper (+1) saltMeSH, HMDB
BenzenethiolMeSH
Benzene, mercapto-biospider
Mercapto-benzeneHMDB
Phenol, thio-biospider
Phenyl mercaptan [UN2337] [Poison]biospider
Thio-phenolHMDB
Predicted Properties
PropertyValueSource
Water Solubility1.17 g/LALOGPS
logP2.26ALOGPS
logP2.07ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.07 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6S
IUPAC namebenzenethiol
InChI IdentifierInChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyRMVRSNDYEFQCLF-UHFFFAOYSA-N
Isomeric SMILESSC1=CC=CC=C1
Average Molecular Weight110.177
Monoisotopic Molecular Weight110.019020882
Classification
Description Belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
KingdomOrganic compounds
Super ClassBenzenoids
ClassThiophenols
Sub ClassNot Available
Direct ParentThiophenols
Alternative Parents
Substituents
  • Thiophenol
  • Monocyclic benzene moiety
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 65.41%; H 5.49%; S 29.10%DFC
Melting PointFp -14.8°DFC
Boiling PointBp30 77°DFC
Experimental Water Solubility0.835 mg/mL at 25 oCWAKITA,K et al. (1986)
Experimental logP2.52HANSCH,C ET AL. (1995)
Experimental pKa6.62
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd254 1.97DFC
Refractive Indexn20D 1.5893DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBenzenethiol, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-f00b12d067160b203ec9Spectrum
GC-MSBenzenethiol, non-derivatized, GC-MS Spectrumsplash10-03xr-9400000000-963c74e11e0fee28cdedSpectrum
GC-MSBenzenethiol, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-f00b12d067160b203ec9Spectrum
GC-MSBenzenethiol, non-derivatized, GC-MS Spectrumsplash10-03xr-9400000000-963c74e11e0fee28cdedSpectrum
Predicted GC-MSBenzenethiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9500000000-39461b1b5833a05c75b9Spectrum
Predicted GC-MSBenzenethiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzenethiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-902e432c58a5b48af6d92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-d103552d249a6486076c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-73bb0429feae5d758aaf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-08819ed59079e9d5777a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-cf3fe95c00ee01bcc7402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-0744499c38c462f823352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-c97d421ad73111f833c12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9300000000-1e8a6992b5b9f0c1bf072021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-bbfc0b211357cbad29c72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9604afb1cae23bc5502c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-9604afb1cae23bc5502c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-51cfb1d93a171cc439c02021-09-25View Spectrum
NMRNot Available
ChemSpider ID7681
ChEMBL IDCHEMBL119405
KEGG Compound IDNot Available
Pubchem Compound ID7969
Pubchem Substance IDNot Available
ChEBI ID48498
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33746
CRC / DFC (Dictionary of Food Compounds) IDHBK74-A:HBK74-A
EAFUS ID301
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDBT6
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1007501
SuperScent IDNot Available
Wikipedia IDBenzenethiol
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
Flavours
FlavorCitations
repulsive
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
penetrating
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
garlic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference