1,4-Dichlorobut-2-ene

1,4-Dichlorobut-2-ene
Names
	IUPAC name 1,4-Dichlorobut-2-ene
	Other names trans-1,4-Dichlorobutene
Identifiers
CAS Number	110-57-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:82446;
ChEMBL	ChEMBL468582;
ChemSpider	557415 ;
ECHA InfoCard	100.003.437
EC Number	203-779-7;
KEGG	C19398;
PubChem CID	642197;
UNII	92HZ946H7Y;
UN number	2920 2927 2922
CompTox Dashboard (EPA)	DTXSID6020434 ;
	InChI InChI=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 Key: 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,3-4H2 Key: FQDIANVAWVHZIR-UHFFFAOYSA-N;
	SMILES ClC/C=C/CCl; ClCC=CCCl;
Properties
Chemical formula	C4H6Cl2
Molar mass	124.99 g·mol−1
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[1]
GHS pictograms	;
GHS Signal word	Danger
GHS hazard statements	H350, H330, H311, H301, H314, H410
GHS precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P307+311, P308+313, P310
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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.[2] The (E)-isomer is also one of the starting materials for Birman's total synthesis of the poriferic natural product sceptrin.[3]

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.[4]

References

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.
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.
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.
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, 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, 6 (4th ed.), New York: John Wiley, pp. 70–78.

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[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.

[sceptrin-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, 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, 6 (4th ed.), New York: John Wiley, pp. 70–78.