Tetrabromoethylene

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Tetrabromoethylene
Tetrabromoethylene.png
Names
Preferred IUPAC name
Tetrabromoethene
Other names
Perbromoethene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.084 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-192-0
PubChem CID
UNII
  • InChI=1S/C2Br4/c3-1(4)2(5)6 X mark.svgN
    Key: OVRRJBSHBOXFQE-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C2Br4/c3-1(4)2(5)6
    Key: OVRRJBSHBOXFQE-UHFFFAOYAE
  • Br(Br)C=CBr(Br)
Properties
C2Br4
Molar mass 343.638 g·mol−1
AppearanceColorless crystal
Melting point 50 °C (122 °F; 323 K)
Boiling point 226 °C (439 °F; 499 K)
−114.8·10−6 cm3/mol
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrabromoethylene is an organobromine compound with the chemical formula C2Br4. Its structure is Br2C=CBr2. Under standard conditions, it exists in a form of colorless crystals. It is a brominated derivative of ethylene. Tetrabromoethylene is a potential fungicide and bactericide on fruits. [1] It was used in mineral separation. [2] It is an irritant. [3]

It is prepared from acetylene and bromine in multiple steps. [1] [4] One method involves dehydrobromination of pentabromoethane, other method involves bromination of dibromoethylene in chloroform. [1] Reaction of mercuric acetylide and bromine also gives tetrabromoethylene. [5] It can be produced by oxybrominating butane with free oxygen and bromine. [6]

Tetrabromoethylene gives tribromoacetyl bromide upon treatment with fuming nitric acid. [7]

See also

References

  1. 1 2 3 Miller, S. A. (1965). Acetylene: Its Properties, Manufacture, and Uses. UK Academic Press.
  2. Chemical and Rubber Industry Report. (1959). U.S. Department. of Commerce, Business and Defense Services Administration, [Chemical and Rubber Division].
  3. https://pubchem.ncbi.nlm.nih.gov/compound/Ethene_-1_1_2_2-tetrabromo
  4. Acetylene, Kroschwitz, J. I. (2004). Kirk-Othmer Encyclopedia of Chemical Technology, Volume 1.
  5. Matyáš, R., Pachman, J. (2013). Primary Explosives. page 319
  6. US 4167528,Uriarte, Anthony K.&Vaughan, James H.,"Process for the production of tetrabromoethylene",published 1979-09-11, assigned to Monsanto Co.
  7. Perekalin, V. V. (1964). Unsaturated Nitro Compounds.