Diphenylchlorarsine (CHEM001127)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (71)XML
Record Information
Version1.0
Creation Date2009-06-19 21:58:35 UTC
Update Date2026-08-18 15:26:29 UTC
Accession NumberCHEM001127
Identification
Common NameDiphenylchlorarsine
ClassSmall Molecule
DescriptionDiphenylchlorarsine is an exogenous organic compound with the formula C12H10AsCl and an average molecular weight of 264.58 g/mol. It exists as a solid at room temperature. Diphenylchlorarsine belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. This compound is recorded as being found in or released from electrical and electronic equipment, specifically magnets, discharge lamps, and coils. The compound interacts with various protein targets. Arsenic binds to hemoglobin subunits alpha (HBA1) and beta (HBB), as well as the glucocorticoid receptor (NR3C1), haptoglobin, and actin variants including ACTA1, ACTA2, ACTB, and ACTG1. It causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor (ESR1 and ESR2). Additionally, arsenic binds glutathione reductase (GSR), resulting in the inhibition of essential biochemical reactions, alteration of cellular redox status, and eventual cytotoxicity. Arsenic disrupts ATP production through several mechanisms. It inhibits pyruvate dehydrogenase (DLAT, PDHA1, PDHA2, and PDHB) at the level of the citric acid cycle and uncouples oxidative phosphorylation by competing with phosphate, which inhibits ATP synthesis, mitochondrial respiration, and energy-linked reduction of NAD+. This process also increases hydrogen peroxide production, potentially forming oxidative stress and reactive oxygen species. Furthermore, arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diphenyl arsine chlorideMeSH
Clark 1MeSH
Chemical FormulaC12H10AsCl
Average Molecular Mass264.582 g/mol
Monoisotopic Mass263.969 g/mol
CAS Registry Number712-48-1
IUPAC Namechloro(diphenyl)arsane
Traditional Namediphenylchloroarsine
SMILESCl[As](C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C12H10AsCl/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
InChI KeyYHHKGKCOLGRKKB-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
  • Trivalent organic arsenic compound
  • Organic metalloid salt
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organoarsenic compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point44°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP4.13ALOGPS
logP4.34ChemAxon
logS-4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.08 m³·mol⁻¹ChemAxon
Polarizability23.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-ce1e7042066fb4ef50e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0290000000-ce73d53764d20190fc11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-3190000000-7d6297d5f7dc8cb71170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-bbd0b5c2afe9caa5ca4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-40a9c3b05a8f24403d3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9880000000-006c911f60dff6e2dc1dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-1910000000-d027ab248c2990efc44cSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityArsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (9, 1)
MetabolismArsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesDiphenylchloroarsine belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases. Due to its toxicity, it is nowadays considered obsolete. (7)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (5) Chronic Oral: 0.0003 mg/kg/day (5) Chronic Inhalation: 0.01 mg/m3 (5)
Health EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (9, 3)
SymptomsExposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of
TreatmentArsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (3)
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 LinkDiphenylchlorarsine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID12836
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available