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Names | |
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IUPAC name
1,2-dibromo-1,1,2,2-tetrachloroethane
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Other names
dibromotetrachloroethane, sym-Dibromotetrachloroethane, DBTCE, Bromure de chloréthose ("bromide of chlorethose")
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
ECHA InfoCard | 100.010.125 |
EC Number |
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PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C2Br2Cl4 | |
Molar mass | 325.63 g·mol−1 |
Appearance | Crystalline solid |
Hazards | |
GHS labelling: [1] | |
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Warning | |
H302, H315, H319, H335 | |
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 [77 °F], 100 kPa).
|
1,2-Dibromotetrachloroethane (DBTCE) is an organohalide with the chemical formula C2Br2Cl4. It is a crystalline solid that emits lachrymatory ( tear-producing) vapours. [2] Dibromotetrachloroethane can be used as a fungicide, [2] flame retardant [3] and a source for bromine in the laboratory. [4] Because the 1,1-dibromotetrachloroethane isomer is rare, 1,2-dibromotetrachloroethane is frequently referred to as simply dibromotetrachloroethane.
Dibromotetrachloroethane decomposes to Tetrachloroethylene and bromine when heated. Reacted with potassium sulphide, it gives tetrachloroethylene, potassium bromide and sulphur: [5]
Dibromotetrachloroethane, when reacted with aniline at 140 to 150 °C, gives pure tetrachloroethylene. [6]
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. [7]
Dibromotetrachloroethane was discovered by the Italian chemist Faustino Malaguti in 1846. [8] 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. [5] Similar to Malaguti's method, modern synthesis of dibromotetrachloroethane uses bromine dissolved in carbon tetrachloride.
![]() | |
Names | |
---|---|
IUPAC name
1,2-dibromo-1,1,2,2-tetrachloroethane
| |
Other names
dibromotetrachloroethane, sym-Dibromotetrachloroethane, DBTCE, Bromure de chloréthose ("bromide of chlorethose")
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.010.125 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C2Br2Cl4 | |
Molar mass | 325.63 g·mol−1 |
Appearance | Crystalline solid |
Hazards | |
GHS labelling: [1] | |
![]() | |
Warning | |
H302, H315, H319, H335 | |
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 [77 °F], 100 kPa).
|
1,2-Dibromotetrachloroethane (DBTCE) is an organohalide with the chemical formula C2Br2Cl4. It is a crystalline solid that emits lachrymatory ( tear-producing) vapours. [2] Dibromotetrachloroethane can be used as a fungicide, [2] flame retardant [3] and a source for bromine in the laboratory. [4] Because the 1,1-dibromotetrachloroethane isomer is rare, 1,2-dibromotetrachloroethane is frequently referred to as simply dibromotetrachloroethane.
Dibromotetrachloroethane decomposes to Tetrachloroethylene and bromine when heated. Reacted with potassium sulphide, it gives tetrachloroethylene, potassium bromide and sulphur: [5]
Dibromotetrachloroethane, when reacted with aniline at 140 to 150 °C, gives pure tetrachloroethylene. [6]
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. [7]
Dibromotetrachloroethane was discovered by the Italian chemist Faustino Malaguti in 1846. [8] 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. [5] Similar to Malaguti's method, modern synthesis of dibromotetrachloroethane uses bromine dissolved in carbon tetrachloride.