Hexachlorobutadiene

HCID 6901CAS 87-68-3

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Basic information

Standard SMILES: ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl
InChIKey: RWNKSTSCBHKHTB-UHFFFAOYSA-N
Molecular formula: C4Cl6
Average molar mass: 260.8 g/mol
Monoisotopic mass: 257.813116

Names & identifiers

Preferred name: Hexachlorobutadiene
IUPAC: 1,1,2,3,4,4-hexachlorobuta-1,3-diene
English name: Hexachloro-1,3-butadiene
Molecular formula: C4Cl6
Molecular weight: 260.76

Names & synonyms

HEXACHLORO-1,3-BUTADIENEHexachlorobutadiene87-68-3PerchlorobutadieneHexachlorobuta-1,3-dieneHCBD1,1,2,3,4,4-hexachlorobuta-1,3-dieneDolen-purHexachlorbutadiene1,3-Butadiene, 1,1,2,3,4,4-hexachloro-1,3-HexachlorobutadieneHexachlor-1,3-butadien

Show more names

c46Butadiene, hexachloro-C 46TripeneHexachL

RCRA waste number U1281,1,2,3,4,4-Hexachloro-1,3-butadienePerchloro-1,3-butadieneDTXSID7020683GP-40-66:120CQ8AAO9MO1NSC-3701DTXCID10683

Database identifiers

CAS: 87-68-3
PubChem CID: 6901
DTXSID: DTXSID7020683
ChEMBL: CHEMBL389950
ChEBI: CHEBI:5691
UNII: CQ8AAO9MO1
EC Number: 201-765-5
Nikkaji: J3.541F

Properties

Computed structural properties

XLogP: 4.8
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 1
Heavy atoms: 10
Formal charge: 0
Complexity: 160

Physicochemical properties

Melting point: -19 °C · -19 °C
Boiling point: 210 · 210-220 °C(lit.)
Density: 1.68 · 1.68
vapor pressure: 0.2 mm · 0.2 mm Hg ( 20 °C)
refractive index: 20 · n20/D 1.555(lit.)
Flash point: 210 · 210-220°C
storage temp.: 4 °C · +4°C
solubility: Soluble in ethanol and ether (U.S. EPA, 1985)
form: liquid, clear
Odor: faint turpentine odor
Water Solubility: 4.78 at · (mg/L):4.78 at 25 °C (shake flask-LSC, Banerjee et al., 1980) 4 at 20–25 °C (Geyer et al., 1980)
Merck: 14 · 14,4678
BRN: 1766570 · 1766570
Henry's Law Constant: 3.55 · 3.55, 5.87, 6.90, 10.5, and 15.3 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)
Exposure limits: 0.2 mg/m3 · PC-TWA:0.2 mg/m3
Dielectric constant: 2.6 · 2.6(Ambient)
Stability: Stable. Incompatible with rubber, oxidizing agents.
InChI: 1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10
InChIKey: RWNKSTSCBHKHTB-UHFFFAOYSA-N
SMILES: Cl\C(Cl)=C(Cl)/C(Cl)=C(\Cl)Cl
Surface tension: 36 mN/m · 36mN/m at 20°C
CAS DataBase Reference: 87 · 87-68-3(CAS DataBase Reference)
EWG's Food Scores: 3 · 3
FDA UNII: 8 AAO9MO1 · CQ8AAO9MO1
Proposition 65 List: Hexachlorobutadiene
IARC: 3 · 3 (Vol. 73) 1999
EPA Substance Registry System: Hexachlorobutadiene (87-68-3)
Toxicological Profile|ATSDR: -1 · Hexachloro-1,3-butadiene|Toxicological Profile|ATSDR
UNSPSC Code: 77101502 · 77101502
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302-H312-H315-H317-H332-H400
Precautionary statements: 264 · P264-P270-P280-P261-P272-P271-P273-P301+P312-P330-P302+P352-P312-P362+P364-P332+P313-P333+P313-P304+P340-P391-P501
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: T,N,F
Risk Statements: 24 · 24/25-34-40-50/53-39/23/24/25-23/24/25-11
Safety Statements: 26 · 26-36/37/39-45-61-60-36/37-16-7
OEB: C
OEL: 0.02 ppm · TWA: 0.02 ppm (0.24 mg/m3) [skin]
RIDADR: 2279 · UN 2279
WGK Germany: 3 · 3
RTECS: 700000 · EJ0700000
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29032990 · 29032990
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 2 DermalAcute · Acute Tox. 2 DermalAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Eye Irrit. 2Skin Irrit. 2
Hazardous Substances Data: 87 · 87-68-3(Hazardous Substances Data)
Toxicity: 50 in · LD50 in male, female mice, rats (mg/kg): 105, 76, 216, 175 i.p.; 80, 65, 250, 270 orally (Gradiski)
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

Safety data

OEB: C
OEL: TWA: 0.02 ppm (0.24 mg/m3) [skin]
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: EJ0700000
ridadr: UN 2279
hs_code: 29032990
Toxicity: LD50 in male, female mice, rats (mg/kg): 105, 76, 216, 175 i.p.; 80, 65, 250, 270 orally (Gradiski)
risk_code: 24/25-34-40-50/53-39/23/24/25-23/24/25-11
Signal word: Warning
Symbol(GHS): GHS07,GHS09
hazard_code: T,N,F
safety_code: 26-36/37/39-45-61-60-36/37-16-7
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
Hazard statements: H302-H312-H315-H317-H332-H400
Limited Quantities: 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Acute Tox. 2 DermalAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P264-P270-P280-P261-P272-P271-P273-P301+P312-P330-P302+P352-P312-P362+P364-P332+P313-P333+P313-P304+P340-P391-P501
Hazardous Substances Data: 87-68-3(Hazardous Substances Data)

Chemistry & industry

Applications · 5 items

DescriptionHexachlorobutadiene was first synthesized in 1877 by chlorination of hexyl iodide. It is an industrial by-product of tetrachloroethylene, trichloroethylene, and perchloroethylene production.

UsesHexachloro-1,3-butadiene is used as an urinary biomarker as a tool for early screening of potential kidney toxicity. Hexachloro-1,3-butadiene (HCBD) causes kidney injury.

UsesIntermediate in the manufacture of rubber Compounds, chlorofluorocarbons, and lubricants. Hydraulic fluid, fluid for gyroscopes, heat transfer fluid, solvent, laboratory reagent. Soil fumigant for vineyards.

UsesProduced as an unwanted by-product during the production of tetrachloroethylene, trichloroethylene, carbon tetrachloride, and chlorine; formerly used as a pesticide in other countries

General DescriptionA colorless liquid with a mild odor. Insoluble in water and denser than water. Nonflammable. May be toxic by ingestion or inhalation. Used as a solvent and heat transfer fluid.