Carbonyl cyanide m-chlorophenyl hydrazone (CHEM001453)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (39)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:28 UTC
Update Date2026-04-04 05:20:16 UTC
Accession NumberCHEM001453
Identification
Common NameCarbonyl cyanide m-chlorophenyl hydrazone
ClassSmall Molecule
DescriptionCarbonyl cyanide m-chlorophenyl hydrazone is a chemical compound of cyanide.
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cyanide Compound
  • Hydrazine
  • Industrial/Workplace Toxin
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3-Chlorophenyl)hydrazonomalononitrileChEBI
[(3-Chlorophenyl)hydrazono]malononitrileChEBI
[(3-Chlorophenyl)hydrazono]propanedinitrileChEBI
Carbonylcyanide-3-chlorophenylhydrazoneChEBI
Carbonyl cyanide m chlorophenyl hydrazoneMeSH
Carbonyl cyanide meta chlorophenyl hydrazoneMeSH
Carbonyl cyanide meta-chlorophenyl hydrazoneMeSH
Chemical FormulaC9H5ClN4
Average Molecular Mass204.616 g/mol
Monoisotopic Mass204.020 g/mol
CAS Registry Number555-60-2
IUPAC NameN-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide
Traditional NameCCCP
SMILESClC1=CC=CC(NN=C(C#N)C#N)=C1
InChI IdentifierInChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H
InChI KeyUGTJLJZQQFGTJD-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
  • Phenylhydrazine
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Nitrile
  • Carbonitrile
  • Hydrazone
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen 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
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point176°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP3.3ALOGPS
logP3.19ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)10.6ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.29 m³·mol⁻¹ChemAxon
Polarizability19.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-3930000000-5f979150543fd51a00e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0udi-2900000000-6e533ba339190c9b3f53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0udi-1900000000-72bc6c8b488e42481083Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udi-0690000000-42813bcf61f8d1e5a263Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-0950000000-1b4f03cb610cde16696eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03xr-9500000000-0bbb2a446a4d8cd609c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0j4i-6900000000-e1e0422b1267e4b7caeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-489f238039bb96ad5d8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-66e8ffe989761257bc9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3490000000-5070ebc12c9a2f315b5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-fe7a2300fdb2f99c70baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-3da66f4d708f96b39376Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4690000000-ac9ffc15a15fe15dda2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-15e0fcfc839c635e1c5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-b3b5ce448b9db35987d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-4900000000-e60f0a2c763074c35a79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-198134c69f22ff575879Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9040000000-43621f23ef9eca2bb6a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-28b6196d8b3508e4d1a7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 Dose213 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 IDHMDB0249720
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarbonyl_cyanide_m-chlorophenyl_hydrazone
Chemspider ID2504
ChEBI ID3259
PubChem Compound ID2603
Kegg Compound IDC11164
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19442682
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25557480
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26208452
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26351918
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29241732
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29277693
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29734380
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=30123191
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31346323
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31956228
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=32936131
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=33096791
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=33790590
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=33837631