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87-68-3
???:
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???(??):
?????-1,3-????;?????????;?????-1,3-????;????????
???:
Hexachloro-1,3-butadiene
???(??):
HEXACHLOROBUTADIENE;HCBD;hexachlorobuta-1,3-diene;c46;Dolen-pur;Hexachlor-1,3-butadien;Butadiene, hexachloro-;C 46;Tripene;HexachL
CBNumber:
CB6854522
???:
C4Cl6
??? ??:
260.76
MOL ??:
87-68-3.mol
MSDS ??:
SDS

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???
-19 °C
?? ?
210-220 °C(lit.)
??
1.68
???
0.2 mm Hg ( 20 °C)
???
n20/D 1.555(lit.)
???
210-220°C
?? ??
+4°C
???
???? ???? ???(US EPA, 1985)
??? ??
??, ??
??
??? ???? ??
???
(mg/L):
4.78 at 25 °C (shake flask-LSC, Banerjee et al., 1980)
4 at 20–25 °C (Geyer et al., 1980)
Merck
14,4678
BRN
1766570
Henry's Law Constant
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)
Dielectric constant
2.6(Ambient)
?? ??
PC-TWA:0.2 mg/m3
???
????. ??, ???? ???? ????.
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
????
36mN/m at 20°C
CAS ??????
87-68-3(CAS DataBase Reference)
IARC
3 (Vol. 73) 1999
EPA
Hexachlorobutadiene (87-68-3)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? T,N,F
?? ???? ?? 24/25-34-40-50/53-39/23/24/25-23/24/25-11
????? 26-36/37/39-45-61-60-36/37-16-7
OEB C
OEL TWA: 0.02 ppm (0.24 mg/m3) [skin]
????(UN No.) UN 2279
WGK ?? 3
RTECS ?? EJ0700000
TSCA TSCA listed
?? ?? 6.1
???? III
HS ?? 29032990
???? ??? 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard Classifications Acute Tox. 2 Dermal
Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
Carc. 2
Eye Irrit. 2
Skin Irrit. 2
?? ?? ??? 87-68-3(Hazardous Substances Data)
?? LD50 in male, female mice, rats (mg/kg): 105, 76, 216, 175 i.p.; 80, 65, 250, 270 orally (Gradiski)
???? ?? KE-05-0685
?????? ??? ??2-23
????(GHS): Exclamation Mark (GHS07)Environment (GHS09)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H302 ??? ??? ?? ?? ?? - ?? ?? 4 ?? P264, P270, P301+P312, P330, P501
H312 ??? ???? ??? ?? ?? ?? - ?? ?? 4 ?? P280,P302+P352, P312, P322, P363,P501
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? P264, P280, P302+P352, P321,P332+P313, P362
H317 ????? ?? ??? ??? ? ?? ?? ??? ?? ?? 1 ?? P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H332 ???? ??? ?? ?? ?? ?? ?? 4 ?? P261, P271, P304+P340, P312
H400 ????? ?? ??? ?? ????? ?? - ?? ?? 1 ?? P273, P391, P501
??????:
P261 ??·?·??·???·??·...·????? ??? ????.
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P270 ? ??? ??? ??? ???, ???? ???? ???.
P271 ?? ?? ??? ? ?? ???? ?????.
P272 ??? ??? ??? ??? ???? ???.
P273 ???? ???? ???.
P280 ????/???/???/?????? ?????.
P301+P312 ??? ???? ??? ????(??)? ??? ????.
P302+P352 ??? ??? ??? ?? ????.
P304+P340 ???? ??? ??? ?? ??? ??? ???? ?? ??? ??? ????.
P312 ???? ??? ????(??)? ??? ????.
P330 ?? ?????.
P332+P313 ?? ??? ??? ???? ??· ??? ????.
P333+P313 ????? ?? ??? ???? ???? ??·??? ????.
P391 ???? ????.
P501 ...? ??? / ??? ?? ???.
NFPA 704
1
3 0

????????? C??? ??, ??, ??

??

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

??? ??

colourless liquid (typical odour recognition threshold:

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Clear, yellowish-green liquid with a mild to pungent, turpentine-like odor. Odor threshold concentration is 6 ppb (quoted, Keith and Walters, 1992).

??

Hexachloro-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.

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A 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.

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Insoluble in water.

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Hexachloro-1,3-butadiene rapidly decomposes rubber on contact. Can react vigorously with oxidizing materials. Reacts to form an explosive product with bromine perchlorate. . Gives highly toxic and irritating chloride fumes when burned.

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Toxic by ingestion and inhalation, a questionable carcinogen.

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Poisonous; may be fatal if inhaled, swallowed or absorbed through the skin. Inhalation causes repiratory difficulty and irritation of mucous membranes. Skin and eye irritant; may cause burns.

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Hexachlorobutadiene is used as a sol vent; heat-transfer fluid; transformer fluid; hydraulic fluid; as a solvent for elastomers; as a wash liquor for removing higher hydrocarbons.

Carcinogenicity

In rats given oral administration, it produced benign and malignant tumors in the kidneys in both sexes. The IARC then concluded that there is limited evidence that HCBD is carcinogenic in rats.
Nakagawa et al. reported that HCBD is a potent nephrotoxicant that selectively damaged the straight portion (pars recta) of the proximal tubule in the rat. They also reported administering 0.1% HCBD for 30 weeks to male Wistar rats previously given 0.1% N-ethyl-N-hydroxyethylnitrosamine (EHEN) in their drinking water for 2 weeks and that the combined treatment resulted in a significantly higher incidence of renal cell tumors than when EHEN was administered alone.

????

Chemical/Physical. Hexachlorobutadiene will not hydrolyze to any reasonable extent (Kollig, 1993).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 258, 91, 21, and 11 mg/g, respectively (Dobbs and Cohen, 1980).

?? ?? ??

In the presence of glutathione (GSH), mouse liver microsomes and cytosol transform 14C-hexachloro- 1,3-butadiene (HCBD) to S- (pentachlorobutadienyl)glutathione (PCBG). PCBG formation in subcellular fractions from a mouse kidney is very limited. After an oral dose of HCBD to mice, PCBG in feces, and S-(pentachlorobutadienyl)-L- cysteine, N-acetyl-S-(pentachlorobutadienyl)-L- cysteine, and 1,1,2,3-tetrachlorobutenoic acid in the urine are identified as the metabolites.

?? ??

UN2279 Hexachlorobutadiene, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Wash the diene with four or five 1/10th volumes of MeOH (or until the yellow colour has been extracted), then stir it for 2hours with H2SO4, wash it with distilled water until neutral and filter it through a column of P2O5. Distil it under reduced pressure through a packed column. [Rytner & Bauer J Am Chem Soc 82 298 1960, Beilstein 1 IV 998.]

? ???

Strong reaction with oxidizers, aluminum powder. Attacks aluminum; some plastics, rubber and coatings

??? ??

High temperature incineration with flue gas scrubbing. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal.

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