Tetrabromoethylene

Tetrabromoethylene

Names
Preferred IUPAC name Tetrabromoethene
Other names Perbromoethene
Identifiers
CAS Number	79-28-7  Y
3D model (JSmol)	Interactive image
ChemSpider	59617  N
ECHA InfoCard	100.001.084
EC Number	201-192-0
PubChem CID	66232
UNII	T686675W6X  Y
CompTox Dashboard (EPA)	DTXSID8058821
InChI InChI=1S/C2Br4/c3-1(4)2(5)6 N Key: OVRRJBSHBOXFQE-UHFFFAOYSA-N N InChI=1/C2Br4/c3-1(4)2(5)6 Key: OVRRJBSHBOXFQE-UHFFFAOYAE
SMILES Br(Br)C=CBr(Br)
Properties
Chemical formula	C2Br4
Molar mass	343.638 g·mol−1
Appearance	Colorless crystals
Melting point	50 °C (122 °F; 323 K)
Boiling point	226 °C (439 °F; 499 K)
Magnetic susceptibility (χ)	−114.8·10−6 cm3/mol
Related compounds
Related compounds	Ethylene Bromoethylene 1,1-Dibromoethylene 1,2-Dibromoethylene Tribromoethylene Tetrafluoroethylene Tetrachloroethylene Tetraiodoethylene Tetrabromomethane Hexabromoethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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

• Tetrachloroethylene
• Tetrafluoroethylene
• Tetraiodoethylene
• Tetrabromoethane

References

1. 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.