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Hexachloropropene

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Hexachloropropene
Names
Preferred IUPAC name 1,1,2,3,3,3-Hexachloroprop-1-ene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.965 Edit this at Wikidata
EC Number
  • 217-560-9
PubChem CID
UNII
UN number 3382 3082
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3Cl6/c4-1(2(5)6)3(7,8)9Key: VFDYKPARTDCDCU-UHFFFAOYSA-N
  • InChI=1/C3Cl6/c4-1(2(5)6)3(7,8)9Key: VFDYKPARTDCDCU-UHFFFAOYAH
SMILES
  • C(=C(Cl)Cl)(C(Cl)(Cl)Cl)Cl
Properties
Chemical formula C3Cl6
Molar mass 248.75 g/mol
Appearance colourless liquid
Density 1.765 g/cm (at 25 °C)
Melting point −73 °C (−99 °F; 200 K)
Boiling point 209–210 °C (408–410 °F; 482–483 K)
Solubility in water 0.25 g/L
Solubility soluble in carbon tetrachloride, ethanol and diethyl ether
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H315, H319, H330, H332, H335
Precautionary statements P260, P261, P264, P271, P280, P284, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P320, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hexachloropropene is a compound of chlorine and carbon with the linear formula CCl3CCl=CCl2. It is a colourless liquid at room temperature. It is toxic for humans.

Hexachloropropene can be produced by the dehydrochlorination reaction of 1,1,1,2,2,3,3-heptachloropropane by potassium hydroxide in methanol solution. 1,1,1,2,2,3,3-Heptachloropropane is produced by the reaction of chloroform and tetrachloroethylene:

CHCl 3 + C 2 Cl 4 ⟶ C 3 HCl 7 {\displaystyle {\ce {CHCl3 + C2Cl4 -> C3HCl7}}}
C 3 HCl 7 + KOH ⟶ C 3 Cl 6 + KCl + H 2 O {\displaystyle {\ce {C3HCl7 + KOH -> C3Cl6 + KCl + H2O}}}

Hexachloropropene can be used to produce other compounds such as uranium tetrachloride, anhydrous niobium pentachloride and tungsten hexachloride.

References

  1. ^ Hexachlorpropen
  2. Gangolli, S.; Royal Society of Chemistry (1999). The dictionary of substances and their effects. Cambridge, UK. p. 607. ISBN 0-85404-803-0. OCLC 41660040.{{cite book}}: CS1 maint: location missing publisher (link)
  3. "Hexachloropropene96%". Sigma Aldrich. Retrieved Nov 27, 2013.
  4. Friedrich Boberg (1964-11-16). "Über 1.2-Dithia-cyclopentene, V. 4.5-Dichlor-1.2-dithia-cyclopentenon-(3)". Justus Liebigs Annalen der Chemie (in German). 679 (1): 109–118. doi:10.1002/jlac.19646790115. Retrieved 2022-03-08.
  5. W. W. Porterfield and S. Y. Tyree, Jr. (1967), S. Young Tyree, Jr. (ed.), Anhydrous metal chlorides, McGraw-Hill Book Company, Inc., pp. 133–136
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