Phenyl isothiocyanate (CHEM000700)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (39)XML
Record Information
Version1.0
Creation Date2009-05-25 19:45:11 UTC
Update Date2026-04-03 07:32:41 UTC
Accession NumberCHEM000700
Identification
Common NamePhenyl isothiocyanate
ClassSmall Molecule
DescriptionPhenyl isothiocyanate is a chemical compound of cyanide. It is a reagent used in reversed phase high-performance liquid chromatography (HPLC). (3)
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cyanide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Benzene-1-isothiocyanateChEBI
Isothiocyanic acid phenyl esterChEBI
Phenyl mustard oilChEBI
PhenylsenfoelChEBI
PITCChEBI
Benzene-1-isothiocyanic acidGenerator
Isothiocyanate phenyl esterGenerator
Phenyl isothiocyanic acidGenerator
PhenylisothiocyanateMeSH
Chemical FormulaC7H5NS
Average Molecular Mass135.186 g/mol
Monoisotopic Mass135.014 g/mol
CAS Registry Number103-72-0
IUPAC Nameisothiocyanatobenzene
Traditional Namephenylisothiocyanate
SMILESS=C=NC1=CC=CC=C1
InChI IdentifierInChI=1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H
InChI KeyQKFJKGMPGYROCL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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-21°C
Boiling PointNot Available
Solubility0.0899 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.08ALOGPS
logP3ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)0.052ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.12 m³·mol⁻¹ChemAxon
Polarizability13.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5900000000-6b9056d45195c7fc337bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-12d2612691131ee796abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-2255176e7585035ef121Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4900000000-d0acbb025959e0ca7146Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ec1b3c4755f5d63fdb4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-ec1b3c4755f5d63fdb4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-5cbab75a9ed479d0e8beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-38280d1452daba11356aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d2da177cd0cbe52b1457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-357d8aff8a89c1194ac5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-b702b7172885d57f90b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-b702b7172885d57f90b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9700000000-581ad8cd00e36ebe2879Spectrum
MSMass Spectrum (Electron Ionization)splash10-002r-9600000000-7d50c10e649cd3a2553eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation (1) ; oral (1) ; dermal (1)
Mechanism of ToxicityCyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)
MetabolismCyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (1)
Toxicity ValuesLD50: 87 mg/kg (Oral, Mouse) (4) LD50: 250 mg/kg (Subcutaneous, Mouse) (4) LD50: 100 mg/kg (Intraperitoneal, Mouse) (4)
Lethal Dose200 to 300 milligrams for an adult human (cyanide salts). (5)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPhenyl isothiocyanate is a reagent used in reversed phase high-performance liquid chromatography (HPLC). (3)
Minimum Risk LevelNot Available
Health EffectsExposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (1, 2)
SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenyl_isothiocyanate
Chemspider IDNot Available
ChEBI ID85103
PubChem Compound ID7673
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=22974327
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24628280
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24852536
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25532938
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=28295200