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1,2-Dibromotetrachloroethane

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1,2-Dibromotetrachloroethane
Names
IUPAC name 1,2-dibromo-1,1,2,2-tetrachloroethane
Other names dibromotetrachloroethane, sym-Dibromotetrachloroethane, DBTCE, Bromure de chloréthose ("bromide of chlorethose")
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.125 Edit this at Wikidata
EC Number
  • 211-136-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2Br2Cl4/c3-1(5,6)2(4,7)8Key: WJUKOGPNGRUXMG-UHFFFAOYSA-N
SMILES
  • ClC(Cl)(Br)C(Cl)(Cl)Br
Properties
Chemical formula C2Br2Cl4
Molar mass 325.63 g·mol
Appearance Crystalline solid
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,2-Dibromotetrachloroethane (DBTCE) is an organohalide with the chemical formula C2Br2Cl4. It is a crystalline solid that emits lachrymatory (tear-producing) vapours. Dibromotetrachloroethane can be used as a fungicide, flame retardant and a source for bromine in the laboratory. Because the 1,1-dibromotetrachloroethane isomer is rare, 1,2-dibromotetrachloroethane is frequently referred to as simply dibromotetrachloroethane.

Reactions and synthesis

Dibromotetrachloroethane decomposes to Tetrachloroethylene and bromine when heated. Reacted with potassium sulphide, it gives tetrachloroethylene, potassium bromide and sulphur:

C2Br2Cl4 + K2S → C2Cl4 + S + 2 KBr

Dibromotetrachloroethane, when reacted with aniline at 140 to 150 °C, gives pure tetrachloroethylene.

When reacted with compounds like cyclohexene, 2,2,4-trimethylpentl-ene, 1-hexene, 1-octene, 2-methyl-1-butene and 2,2,4-trimethyl-2-pentene, it yields allylic monobromides via bromination. Dibromotetrachloroethane loses both of its bromine atoms, leaving tetrachloroethylene and hydrogen bromide.

Dibromotetrachloroethane was discovered by the Italian chemist Faustino Malaguti in 1846. Malaguti exposed a mixture of Tetrachloroethylene (then known as chloréthose) and bromine to sunlight. It was named Bromure de chloréthose ("bromide of chlorethose") after its synthesis method. Similar to Malaguti's method, modern synthesis of dibromotetrachloroethane uses bromine dissolved in carbon tetrachloride.

References

  1. "1,2-Dibromotetrachloroethane". pubchem.ncbi.nlm.nih.gov.
  2. ^ Dewayne Torgeson, Agricultural and Industrial Applications Environmental Interactions: An Advanced Treatise (2012), p. 333
  3. Richard Montgomery Stephenson, Stanisław Malanowski, Handbook of the Thermodynamics of Organic Compounds (2012), p.20
  4. B. Iddon, Basil John Wakefield, D. Price, Bromine Compounds: Chemistry and Applications (1988)
  5. ^ Edmond Frémy, Paul Louis Chastain, Encyclopédie Chimique (1883) p. 235
  6. E. Burgoin, Preparation of Perchlorethylene (1870)
  7. G. H. Williams Advances in Free-radical Chemistry (1972), p. 186
  8. Faustino Malaguti, Recherches sur Éthers Chlorés, Annales de Chimie et de Physique, 16-3, p. 24
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