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]
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| Names | |
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| Preferred IUPAC name
1,2-Dichlorobutane | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.003.436 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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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).
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Preparation and reactions
edit1,4-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
edit- ^ 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.