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1,4-Dichlorobut-2-ene

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Chemical compound
1,4-Dichlorobut-2-ene
1,4-Dichlorobut-2-ene molecule
Names
IUPAC name 1,4-Dichlorobut-2-ene
Other names trans-1,4-Dichlorobutene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.437 Edit this at Wikidata
EC Number
  • 203-779-7
KEGG
PubChem CID
UNII
UN number 2920 2927 2922
CompTox Dashboard (EPA)
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 124.99 g·mol
Appearance Colorless liquid
Density 1.13 g/mL
Melting point 1 °C (34 °F; 274 K)
Boiling point 125.5 °C (257.9 °F; 398.6 K)
Hazards
GHS labelling:
Pictograms GHS06: Toxic GHS08: Health hazard
GHS05: Corrosive GHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H311, H314, H330, H350, H410
Precautionary statements P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH=CHCH2Cl. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene.

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 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.

Other reactions

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

  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.
  3. 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.
  4. Albert I. Meyers, Joseph S. Warmus, Garrett J. Dilley (1996). "3-Pyrroline". Organic Syntheses. 73: 246. doi:10.15227/orgsyn.073.0246.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. 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.
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