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2,3-Dichlorobutadiene

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2,3-Dichlorobutadiene
Names
Preferred IUPAC name 2,3-Dichlorobuta-1,3-diene
Other names 2,3-Dichloro-1,3-butadiene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.202 Edit this at Wikidata
EC Number
  • 216-721-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4Cl2/c1-3(5)4(2)6/h1-2H2Key: LIFLRQVHKGGNSG-UHFFFAOYSA-N
SMILES
  • C=C(C(=C)Cl)Cl
Properties
Chemical formula C4H4Cl2
Molar mass 122.98 g·mol
Appearance Colorless liquid
Density 1.1829 g/cm
Boiling point 98 °C (208 °F; 371 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H225, H301, H302, H304, H315, H319, H330, H335, H411
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P331, P332+P313, P337+P313, P362, 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). Infobox references
Chemical compound

2,3-Dichlorobutadiene is a chlorinated derivative of butadiene. This colorless liquid is prone to polymerization, more so than 2-chlorobutadiene. It is used to produce specialized neoprene rubbers.

It can be prepared by the copper-catalyzed isomerization of dichlorobutynes. Alternatively dehydrochlorination of 2,3,4-trichloro-1-butene:

CH2=C(Cl)CH(Cl)CH2Cl + NaOH → CH2=C(Cl)C(Cl)=CH2 + NaCl + H2O

2,3-Dichlorobutadiene is a precursor to 2,3-diarylbutadienes.

References

  1. M. Rossberg; et al. (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3527306732.
  2. Yamamoto Takakazu; Yasuda Takuma; Kobayashi Kazuaki; et al. (2006). "Utilization of Industrially Available 2,3-Dichloro-1,3-butadiene for Direct Synthesis of 2,3-Diaryl-1,3-butadienes". Bulletin of the Chemical Society of Japan. 79 (3): 498–500. doi:10.1246/bcsj.79.498.
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