1,4-Dichlorobutane

1,4-Dichlorobutane is a chloroalkane with the molecular formula (CH2CH2Cl)2. It is one of several structural isomers of dichlorobutane. They are all colorless liquids of low flammabiltity and of interest for specialized synthetic uses.[1]

1,4-Dichlorobutane
Names
Preferred IUPAC name
1,4-Dichlorobutane
Identifiers
3D model (JSmol)
ECHA InfoCard 100.003.436
UNII
  • InChI=1S/C4H8Cl2/c5-3-1-2-4-6/h1-4H2
    Key: KJDRSWPQXHESDQ-UHFFFAOYSA-N
  • C(CCCl)CCl
Properties
C4H8Cl2
Molar mass 127.01 g·mol−1
Density 1.16 g.mL−1
Boiling point 161–163 °C (322–325 °F; 434–436 K)
Related compounds
Related compounds
 1,4-Dichlorobut-2-ene
4-Fluorobutanol
1,4-Butanediol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation and reactions

1,4-Dichlorobutane can be obtained from 1,4-butanediol as well as from tetrahydrofuran.[1]

1,4-Dihalobutanes are well suited for the synthesis of 5-membered ring heterocyces. For example, treatment with sodium sulfide gives tetrahydrothiophene.[2] Treatment with lithium wire gives 1,4-dilithiobutane.[3]

1,4-Dichlorobutane can be used, among others, as a precursor for nylon 6,6 (via adiponitrile).[4][1]

References
  1. Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2.
  2. J. Keith Lawson; William K. Easley; William S. Wagner (1956). "Tetrahydrothiophene". Organic Syntheses. 36: 89. doi:10.15227/orgsyn.036.0089.
  3. Paul A. Wender; Alan W. White; Frank E. McDonald (1992). "Spiroannelation Via Organobis(Cuprates): 9,9-Dimethylspiro[4.5]Decan-7-One". Organic Syntheses. 70: 204. doi:10.15227/orgsyn.070.0204.
  4. Mark S. M. Alger (1997). Polymer Science Dictionary. Springer. p. 241. ISBN 0-412-60870-7. Retrieved August 28, 2008.
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