1,4-Dichlorobut-2-ene

Chemical compound From Wikipedia, the free encyclopedia

1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH=CHCH2Cl. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene.[2]

Quick facts Names, Identifiers ...
1,4-Dichlorobut-2-ene
1,4-Dichlorobut-2-ene molecule
Names
IUPAC name
1,4-Dichlorobut-2-ene
Other names
trans-1,4-Dichlorobutene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.437 Edit this at Wikidata
EC Number
  • 203-779-7
KEGG
UNII
UN number 2920 2927 2922
  • InChI=1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 checkY
    Key: FQDIANVAWVHZIR-UHFFFAOYSA-N checkY
  • 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
  • ClC/C=C/CCl
  • ClCC=CCCl
Properties
C4H6Cl2
Molar mass 124.99 g·mol−1
Appearance Colorless liquid
Density 1.13 g/mL
Melting point 1 Â°C (34 Â°F; 274 K)
Boiling point 125.5 Â°C (257.9 Â°F; 398.6 K)
Hazards[1]
GHS labelling:
GHS06: Toxic GHS08: Health hazard
GHS05: Corrosive GHS09: Environmental hazard
Danger
H301, H311, H314, H330, H350, H410
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Synthesis and reactions

1,4-Dichlorobut-2-ene (both isomers) are produced by chlorination of butadiene:

CH2=CHCH=CH2 + Cl2 → ClCH2CH=CHCH2Cl

It is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 Â°C in the presence of a catalyst:

ClCH2CH=CHCH2Cl → ClCH2CHClCH=CH2

The resulting 3,4-dichlorobut-1-ene is a precursor to chloroprene, the monomer for the synthetic rubber neoprene.[3]

1,4-Dichlorobut-2-ene is a precursor to various heterocycles.[4] The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin.[5]

References

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