2,3-Dichlorobutadiene

2,3-Dichlorobutadiene
Names
	Preferred IUPAC name 2,3-Dichlorobuta-1,3-diene
	Other names 2,3-Dichloro-1,3-butadiene
Identifiers
CAS Number	1653-19-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	14699;
ECHA InfoCard	100.015.202
EC Number	216-721-0;
PubChem CID	15447;
UNII	SG9RMT8EAJ ;
CompTox Dashboard (EPA)	DTXSID1027423 ;
	InChI InChI=1S/C4H4Cl2/c1-3(5)4(2)6/h1-2H2 Key: LIFLRQVHKGGNSG-UHFFFAOYSA-N;
	SMILES C=C(C(=C)Cl)Cl;
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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:^[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

^ 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.
^ 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.

[Ullmann-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.

[1]

[2]