1,4-Dichlorobut-2-ene

Chemical compound changed changed 477206209 trans-1,4-Dichlorobutene.svg 1,4-Dichlorobut-2-ene-3D-balls.png 1,4-Dichlorobut-2-ene molecule 1,4-Dichlorobut-2-ene trans-1,4-Dichlorobutene 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+ correct chemspider 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 FQDIANVAWVHZIR-OWOJBTEDBY correct chemspider FQDIANVAWVHZIR-UHFFFAOYSA-N correct chemspider 557415 ClC/C=C/CCl 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 FQDIANVAWVHZIR-UHFFFAOYSA-N ClCC=CCCl changed ?? 110-57-6 203-779-7 642197 2920 2927 2922 92HZ946H7Y 82446 C19398 468582 4 6 2 1.13 g/mL 1 125.5 Colorless liquid 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. skull and crossbones health hazardcorrosion environment DANGER 350 330 311 301 314 410 201 202 210 233 240 241 242 243 260 264 270 271 273 280 281 284 301+310 301+330+331 302+352 303+361+353 304+340 305+351+338 307+311 308+313 310 312 314 320 321 322 330 361 363 370+378 391 403+233 403+235 405 501 1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH\dCHCH2Cl. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene. 227–50 http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-9.pdf IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 71 International Agency for Research on Cancer Lyon, France Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide 1999 92-832-1271-1. Synthesis and reactions 1,4-Dichlorobut-2-ene (both isomers) are produced by chlorination of butadiene: CH2\dCHCH\dCH2 + Cl2 -> ClCH2CH\dCHCH2Cl It is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst: ClCH2CH\dCHCH2Cl -> ClCH2CHClCH\dCH2 The resulting 3,4-dichlorobut-1-ene is a precursor to chloroprene, the monomer for the synthetic rubber neoprene.Rossberg M. Lendle W. Pfleiderer G. Tögel A. Dreher E.-L. Langer E. Rassaerts H. Kleinschmidt P. Strack H. Cook R. Beck U. Lipper K.-A. Torkelson T. R. Löser E. Beutel K.K. Mann T. Chlorinated Hydrocarbons 15 July 2006 10.1002/14356007.a06_233.pub2 Stewart C. A. Jr. 1993 Chlorocarbons, -hydrocarbons (chloroprene) Kroschwitz J. I. Howe-Grant M. Kirk-Othmer Encyclopedia of Chemical Technology 4th 6 New York John Wiley 70–78. 1,4-Dichlorobut-2-ene is a precursor to various heterocycles.10.15227/orgsyn.073.0246 free Albert I. Meyers, Joseph S. Warmus, Garrett J. Dilley 3-Pyrroline Organic Syntheses 1996 73 246 The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin. Birman Vladimir B. Jiang Xun-Tian Synthesis of Sceptrin Alkaloids Org. Lett. 2004 6 14 2369–71 10.1021/ol049283g 15228281. Baran Phil S. Zografos Alexandros L. O'Malley Daniel P. Phil S. Baran Short Total Synthesis of (±)-Sceptrin J. Am. Chem. Soc. 2004 126 12 3726–27 10.1021/ja049648s 15038721. References Category:Chloroalkenes