1,2-Dibromoethylene
Chemical compound
From Wikipedia, the free encyclopedia
1,2-Dibromoethylene, also known as 1,2-dibromoethene and acetylene dibromide, is a dihalogenated unsaturated compound with one bromine on each of the two carbon atoms. There are two isomers of this compound, cis and trans. Both isomers are colorless liquids.
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| Names | |||
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| Preferred IUPAC name
1,2-Dibromoethene | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.007.953 | ||
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C2H2Br2 | |||
| Molar mass | 185.846 g·mol−1 | ||
| Appearance | colorless liquid | ||
| Density | 2.246 g/cm3 | ||
| Boiling point | 110 °C (230 °F; 383 K) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards |
Toxic | ||
| GHS labelling:[1] | |||
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| Danger | |||
| H301, H315, H319, H335 | |||
| P261, P264, P270, P301+P310, P302+P352, P305+P351+P338 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
1,2-Dibromoethylene can be synthesized by halogenation of acetylene (C2H2) with bromine (Br2).[2] In order to prevent the formation of tetrahalogenated compounds, acetylene is used in excess, with Br2 as the limiting reagent.
Alternately, halogenation of this kind could also be achieved through the use of two equivalents of N-bromosuccinimide and lithium bromide (LiBr). N-Bromosuccinimide provides Br+ as an electrophile, which is followed by Br− from LiBr.[3]
