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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
- 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.
- (1999). "Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide". International Agency for Research on Cancer.
- Stewart, C. A. Jr.. (15 July 2006). "Chlorinated Hydrocarbons". John Wiley.
- Albert I. Meyers, Joseph S. Warmus, Garrett J. Dilley. (1996). "3-Pyrroline". Organic Syntheses.
- (2004). "Synthesis of Sceptrin Alkaloids". Org. Lett..
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