Tetrabromoethylene

Tetrabromoethylene
Names
	Preferred IUPAC name Tetrabromoethene
	Other names Perbromoethene
Identifiers
CAS Number	79-28-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	59617 ;
ECHA InfoCard	100.001.084
EC Number	201-192-0;
PubChem CID	66232;
UNII	T686675W6X ;
CompTox Dashboard (EPA)	DTXSID8058821 ;
	InChI InChI=1S/C2Br4/c3-1(4)2(5)6 Key: OVRRJBSHBOXFQE-UHFFFAOYSA-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 crystal
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). verify (what is ?) 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]

References

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

[miller-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].

[pubchem-3] ttps://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.

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See also

References