1,4-Dichlorobutane

1,4-Dichlorobutane
Names
	Preferred IUPAC name 1,2-Dichlorobutane
Identifiers
CAS Number	110-56-5 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.003.436
PubChem CID	8059;
UNII	8326YNM2B3 ;
CompTox Dashboard (EPA)	DTXSID5021918 ;
	InChI InChI=1S/C4H8Cl2/c5-3-1-2-4-6/h1-4H2 Key: KJDRSWPQXHESDQ-UHFFFAOYSA-N;
	SMILES C(CCCl)CCl;
Properties
Chemical formula	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	1,2-Dichlorobut-2-ene; 4-Fluorobutanol; 1,2-Butanediol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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

^ ^a ^b ^c Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 3527306730.
^ J. Keith Lawson; William K. Easley; William S. Wagner (1956). "Tetrahydrothiophene". Organic Syntheses. 36: 89. doi:10.15227/orgsyn.036.0089.
^ 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.
^ Mark S. M. Alger (1997). Polymer Science Dictionary. Springer. p. 241. ISBN 0-412-60870-7. Retrieved August 28, 2008.

[Ullmann-1] Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 3527306730.

[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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