Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (CHEM001454)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (39)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:28 UTC
Update Date2026-04-04 18:48:31 UTC
Accession NumberCHEM001454
Identification
Common NameCarbonyl cyanide-p-trifluoromethoxyphenylhydrazone
ClassSmall Molecule
DescriptionCarbonyl cyanide-p-trifluoromethoxyphenylhydrazone is a chemical compound of cyanide.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Cyanide Compound
  • Ether
  • Hydrazine
  • Industrial/Workplace Toxin
  • Nitrile
  • Organic Compound
  • Organofluoride
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Carbonyl cyanide 4-trifluoromethoxyphenylhydrazoneChEBI
Carbonylcyanide-p-trifluoromethoxyphenylhydrazoneChEBI
FCCPChEBI
(4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrileMeSH
Carbonyl cyanide p trifluoromethoxyphenylhydrazoneMeSH
Carbonyl cyanide p-trifluoromethoxyphenylhydrazoneMeSH
Carbonyl cyanide para trifluoromethoxyphenylhydrazoneMeSH
Carbonyl cyanide para-trifluoromethoxyphenylhydrazoneMeSH
Cyanide p-trifluoromethoxyphenylhydrazone, carbonylMeSH
Cyanide para-trifluoromethoxyphenylhydrazone, carbonylMeSH
p-Trifluoromethoxyphenylhydrazone, carbonyl cyanideMeSH
Para-trifluoromethoxyphenylhydrazone, carbonyl cyanideMeSH
Chemical FormulaC10H5F3N4O
Average Molecular Mass254.168 g/mol
Monoisotopic Mass254.042 g/mol
CAS Registry Number370-86-5
IUPAC Name1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide
Traditional Name1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide
SMILESFC(F)(F)OC1=CC=C(NN=C(C#N)C#N)C=C1
InChI IdentifierInChI=1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H
InChI KeyBMZRVOVNUMQTIN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylhydrazines
Direct ParentPhenylhydrazines
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Phenylhydrazine
  • Trihalomethane
  • Hydrazone
  • Carbonitrile
  • Nitrile
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Halomethane
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • 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 Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point174°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.23ALOGPS
logP4.02ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.2ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.55 m³·mol⁻¹ChemAxon
Polarizability20.41 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2920000000-cfb16fdfcc44d7812a2aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-77a333a583432590c9d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-89aa39a0bba6618e950fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-5900000000-1679ff5b81d2b8d12c87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-22240f4c6e8a7634382fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-0812fbc453d99d7a0ca7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-01b372bb866969c75d30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-1cf59e0d8451bd5948fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-9351ca87a2ea0477633aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-7910000000-ee04bcbade3c4265a638Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d16410e4d37928d9fd34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-e122b3230b37f579ffe4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-3900000000-e6ce98afba1096512079Spectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide 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)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed 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 ValuesNot Available
Lethal Dose214 to 300 milligrams for an adult human (cyanide salts). (3)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
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)
TreatmentAntidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0252179
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-10715
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarbonyl_cyanide-p-trifluoromethoxyphenylhydrazone
Chemspider ID3213
ChEBI ID75458
PubChem Compound ID3330
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=18221415
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20445170
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21308897
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22343009
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23376234
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23376829
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23529126
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23626747
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23645464
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23830853
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23832656
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23851285
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23876326
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23891695