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1,4-Dichlorobut-2-ene

Identifiers
CAS Number	110-57-6
3D model (JSmol)	Interactive image Interactive image
ChemSpider	14394
ECHA InfoCard	100.003.437
CompTox Dashboard (EPA)	DTXSID6020434
InChI InChI=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2Key: FQDIANVAWVHZIR-UHFFFAOYSA-N InChI=1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+Key: FQDIANVAWVHZIR-OWOJBTEDBY InChI=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2Key: FQDIANVAWVHZIR-UHFFFAOYSA-N
SMILES ClC/C=C/CCl ClCC=CCCl
Properties
Chemical formula	C4H6Cl2
Molar mass	125.00 g/mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H314, H330, H350, H410
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

1,4-Dichlorobut-2-ene is a chlorinated butene. It is an intermediate in the industrial production of chloroprene, and the main impurity in technical grade chloroprene. The (E)-isomer is also one of the starting materials for Birman's total synthesis of the poriferic natural product sceptrin.

Production of chloroprene

Chloroprene is a monomer for the production of synthetic rubbers such as Neoprene. It is produced from butadiene in a three-step process. The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to pure 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst. Finally, dehydrochlorination (elimination of hydrogen chloride) of 3,4-dichlorobut-1-ene with dilute sodium hydroxide solution in the presence of polymerization inhibitors gives crude chloroprene.

References

1. Index no. 602-073-00-X of Annex VI, Part 3, to 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. , Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (PDF), IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 71, Lyon, France: International Agency for Research on Cancer, 1999, pp. 227–50, ISBN 92-832-1271-1 {{citation}}: |chapter-url= missing title (help); Check |chapter-url= value (help).
3. Birman, Vladimir B.; Jiang, Xun-Tian (2004), "Synthesis of Sceptrin Alkaloids", Org. Lett., 6 (14): 2369–71, doi:10.1021/ol049283g, PMID 15228281. Baran, Phil S.; Zografos, Alexandros L.; O'Malley, Daniel P. (2004), "Short Total Synthesis of (±)-Sceptrin", J. Am. Chem. Soc., 126 (12): 3726–27, doi:10.1021/ja049648s, PMID 15038721.
4. Kleinschmidt, P. (1986), "Chlorinated hydrocarbons. 6.4. 2-Chloro-1,3-butadiene", in Gerhartz, W.; Yamamoto, Y. S. (eds.), Ullmann’s Encyclopedia of Industrial Chemistry, vol. A6 (5th ed.), Weinheim: VCH, pp. 315–18. Stewart, C. A., Jr. (1993), "Chlorocarbons, -hydrocarbons (chloroprene)", in Kroschwitz, J. I.; Howe-Grant, M. (eds.), Kirk-Othmer Encyclopedia of Chemical Technology, vol. 6 (4th ed.), New York: John Wiley, pp. 70–78{{citation}}: CS1 maint: multiple names: authors list (link).

• Orphaned articles from January 2010
• Alkenes
• Organochlorides