2,3-Dichlorobutadiene

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.

2,3-Dichlorobutadiene
Names
Preferred IUPAC name
2,3-Dichlorobuta-1,3-diene
Other names
2,3-Dichloro-1,3-butadiene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.202
EC Number
  • 216-721-0
UNII
  • InChI=1S/C4H4Cl2/c1-3(5)4(2)6/h1-2H2
    Key: LIFLRQVHKGGNSG-UHFFFAOYSA-N
  • C=C(C(=C)Cl)Cl
Properties
C4H4Cl2
Molar mass 122.98 g·mol−1
Appearance Colorless liquid
Density 1.1829 g/cm3
Boiling point 98 °C (208 °F; 371 K)
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H301, H302, H304, H315, H319, H330, H335, H411
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 [77 °F], 100 kPa).
Infobox references

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

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.[2]

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.
  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: 498–500. doi:10.1246/bcsj.79.498.
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