Hexachlorocyclopentadiene (CHEM000151)

Record Information
Version1.0
Creation Date2009-03-06 18:58:12 UTC
Update Date2026-08-22 19:40:01 UTC
Accession NumberCHEM000151
Identification
Common NameHexachlorocyclopentadiene
ClassSmall Molecule
Description
Hexachlorocyclopentadiene (HCCPD) is a light, lemon-yellow liquid that has a sharp, musty odor. It easily turns from a liquid to a vapor when exposed to air. The vapor looks like a blue haze. HCCPD is a manufactured chemical and does not occur naturally in the environment. It is made by adding chlorine to cyclopentadiene, or by removing chlorine from octachlorocyclopentane. HCCPD is used to make a group of related pesticides (aldrin, chlordane, dieldrin, endosulfan, endrin, heptachlor, isodrin, mirex, and pentac) referred to cyclodienes. Only two of these pesticides, endosulfan and pentac, are currently registered for use in the United States. (1)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC5Cl6
Average Molecular Mass272.772 g/mol
Monoisotopic Mass269.813 g/mol
CAS Registry Number77-47-4
IUPAC Namehexachlorocyclopenta-1,3-diene
Traditional Namehexachlorocyclopentadiene
SMILESClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl
InChI IdentifierInChI=1S/C5Cl6/c6-1-2(7)4(9)5(10,11)3(1)8
InChI KeyVUNCWTMEJYMOOR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-9°C
Boiling Point239°C
Solubility0.0018 mg/mL at 25 °C [CALLAHAN,MA et al. (1979)]
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP4.85ALOGPS
logP3.57ChemAxon
logS-5.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.01 m³·mol⁻¹ChemAxon
Polarizability20.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of Exposure Inhalation (2) ; oral (2) ; dermal (2) ; eye contact (2)
Mechanism of ToxicityHCCPD may interact with the microsomes that binds to secretory molecules and changes their ability to be transported from the cell. It can be postulated, that some of its toxic properties are a consequence of its reactivity in Diels-Alder reactions where a conjugated diene combines with a substituted or unsubstituted alkene (a dienophile) in a cycloaddition reaction. Biological tissues contain a large number of potential reactants for cycloaddition reactions. HCCPD can also undergo addition and substitution reactions or be oxidized by way of the mixed function oxidase system. Effects of HCCPD on the brain may also be a reflection of the reaction of either HCCPD or a metabolite with brain lipids. The effects of HCCPD on the adrenal glands may be a reflection of its ability to combine with the unsaturated carbons in sterols produced by this gland. The hydroxyl functional group of a sterol is on a carbon adjacent to the double bond and can activate that bond to cycloaddition reactions. Such reactions would require exposure to large doses of HCCPD so that reactive material would reach the adrenal gland. HCCPD is excreted in urine and feces. (1)
MetabolismHCCPD is rapidly metabolized and distributed to blood, liver, kidneys, and lungs before being distributed to the peripheral tissues. (1)
Toxicity ValuesLD50: 471 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesHCCPD is used to make a group of related pesticides (aldrin, chlordane, dieldrin, endosulfan, endrin, heptachlor, isodrin, mirex, and pentac) referred to cyclodienes. Exposure may result from eating contaminated food, drinking contaminated water, and exposing the skin or eye to hexachlorocyclopentadiene. (1)
Minimum Risk LevelIntermediate Inhalation: 0.01 ppm (Rat) (1) Chronic Inhalation 0.2 ppb (Rat) (1) Intermediate Oral: 0.1 mg/kg/day (Rat) (1)
Health EffectsPatients exposed to HCCPD may get a sore throat or have shortness of breath and chest discomfort. Bleeding, swelling, and fluid buildup can occur in the lungs. The linings of the respiratory passages and the lungs are very susceptible to damage from low concentrations of HCCPD following inhalation exposure. Inflammation of the tissues can be followed by necrosis, exfoliation, and hemorrhage. Tissue repair is often fibrous in appearance. Long-term exposure to very low levels of HCCPD can produce granular yellow-brown pigmentation of the epithelium of the nose, trachea, larynx, and lungs. High acute oral doses of HCCPD are associated with liver necrosis and tissue degeneration. The kidneys also appear to be a target tissue for HCCPD toxicity. Degenerative lesions in the tubules can result from small oral doses. (1)
SymptomsInhalation of HCCPD can cause cough, sore throat, headache, diarrhoea, dizziness, nausea, vomiting, and laboured breathing. Ingestion of HCCPD can cause abdominal pain,burning sensation, shock or collapse. Dermal exposure can cause redness, pain and skin burns. Eye exposure can cause redness, pain, blurred vision, and severe deep burns. (2)
TreatmentAfter oral exposure of HCCPD, gastric lavage is recommended. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact with the toxin, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (3)
Concentrations
Not Available
External Links
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 LinkHexachlorocyclopentadiene
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6478
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References