Benzenethiol (CHEM004144)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:35:50 UTC
Update Date2016-11-09 01:09:17 UTC
Accession NumberCHEM004144
Identification
Common NameBenzenethiol
ClassSmall Molecule
DescriptionA thiol in which the sulfanyl group is attached to a phenyl group.
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC6H6S
Average Molecular Mass110.177 g/mol
Monoisotopic Mass110.019 g/mol
CAS Registry Number108-98-5
IUPAC Namebenzenethiol
Traditional Namethiophenol
SMILESSC1=CC=CC=C1
InChI IdentifierInChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyRMVRSNDYEFQCLF-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
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)splash10-03di-8900000000-f00b12d067160b203ec9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cdedSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-f00b12d067160b203ec9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cdedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9500000000-39461b1b5833a05c75b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-902e432c58a5b48af6d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-d103552d249a6486076cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-73bb0429feae5d758aafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-08819ed59079e9d5777aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-cf3fe95c00ee01bcc740Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-0744499c38c462f82335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-c97d421ad73111f833c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9300000000-1e8a6992b5b9f0c1bf07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-bbfc0b211357cbad29c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9604afb1cae23bc5502cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-9604afb1cae23bc5502cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-51cfb1d93a171cc439c0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033746
FooDB IDFDB011878
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-8132
METLIN IDNot Available
PDB IDBT6
Wikipedia LinkThiophenol
Chemspider ID7681
ChEBI ID48498
PubChem Compound ID7969
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23902004
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23961762
3. Patil G, Rudolph R, Lange C: In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols. J Biotechnol. 2008 Apr 30;134(3-4):218-21. doi: 10.1016/j.jbiotec.2008.01.009. Epub 2008 Jan 18.
4. Park G, Lee KG, Lee SJ, Park TJ, Wi R, Wang KW, Kim DH: Ultrasound-aided formation of gold nanoparticles on multi-walled carbon nanotubes functionalized with mercaptobenzene moieties. J Nanosci Nanotechnol. 2011 Jul;11(7):6222-6.
5. Montanari L, Pavanetto F, Modena T, Mazza M: [Antifungal activity of diesters of 2-mercaptobenzene methanethiol]. Farmaco Sci. 1982 Nov;37(11):759-63.
6. Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK, Phillips E, Kiddle JJ, Tu C, Silverman DN, Govindasamy L, Agbandje-McKenna M, McKenna R, Tripp BC: Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry. 2008 Mar 11;47(10):3174-84. doi: 10.1021/bi702385k. Epub 2008 Feb 12.
7. SCHNITZER RJ, KELLY DR, SOO-HOO G, GRUNBERG E, UNGER C: Chemotherapeutic studies on a new stibonic acid, 2-carboxymethyl-mercaptobenzene stibonic acid, Ro 2-1160. Arch Int Pharmacodyn Ther. 1951 Jan;85(1-2):100-11.
8. Harnisch JA, Pris AD, Porter MD: Attachment of gold nanoparticles to glassy carbon electrodes via a mercaptobenzene film. J Am Chem Soc. 2001 Jun 20;123(24):5829-30.
9. WAGNER G, LENK C: [On the preparation and properties of amino-mercaptobenzene-N,S-bis-glycosides]. Arch Pharm. 1962 Jun;295/67:415-27.
10. Hochalter JB, Wattenberg LW, Coccia JB, Galbraith AR: Inhibition of beta-propiolactone-induced neoplasia of the forestomach and large bowel by 4-mercaptobenzene sulfonate in mice and rats. Cancer Res. 1988 May 15;48(10):2740-3.
11. Mirek J, Chojnacka-Wojcik E, Tatarzynska E, Wiczynska B: Synthesis of 3-phenyl-3-phenylthiopropionic acids, amides, amines and studies on their pharmacological properties. Farmaco Sci. 1985 Sep;40(9):701-8.
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.