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1,4-Dichlorobut-2-ene

Chemical compound


Chemical compound

1,4-Dichlorobut-2-ene are organochlorine compounds with the formula . Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene.

Synthesis and reactions

1,4-Dichlorobut-2-ene (both isomers) are produced by chlorination of butadiene: : It is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst: : The resulting 3,4-dichlorobut-1-ene is a precursor to chloroprene, the monomer for the synthetic rubber neoprene.

1,4-Dichlorobut-2-ene is a precursor to various heterocycles. The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin.

References

References

  1. Index no. 602-073-00-X of Annex VI, Part 3, to [http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:353:0001:1355:EN:PDF Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006]. ''OJEU'' L353, 31.12.2008, pp 1–1355 at p 473.
  2. (1999). "Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide". International Agency for Research on Cancer.
  3. Stewart, C. A. Jr.. (15 July 2006). "Chlorinated Hydrocarbons". John Wiley.
  4. Albert I. Meyers, Joseph S. Warmus, Garrett J. Dilley. (1996). "3-Pyrroline". Organic Syntheses.
  5. (2004). "Synthesis of Sceptrin Alkaloids". Org. Lett..
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