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1,4-Dichlorobutane

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1,4-Dichlorobutane
Names
Preferred IUPAC name 1,2-Dichlorobutane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.436 Edit this at Wikidata
EC Number
  • 203-778-1
PubChem CID
UNII
UN number 1993
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8Cl2/c5-3-1-2-4-6/h1-4H2Key: KJDRSWPQXHESDQ-UHFFFAOYSA-N
SMILES
  • C(CCCl)CCl
Properties
Chemical formula C4H8Cl2
Molar mass 127.01 g·mol
Density 1.16 g.mL
Boiling point 161–163 °C (322–325 °F; 434–436 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H315, H319, H335, H412
Precautionary statements P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
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 , 100 kPa). Infobox references
Chemical compound

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.

Preparation and reactions

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

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

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

References

  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-DimethylspiroDecan-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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