1-Bromo-4-iodobenzene
Chemical compound
From Wikipedia, the free encyclopedia
1-Bromo-4-iodobenzene is a mixed aryl halide (aryl bromide and aryl iodide) with the formula BrC6H4I.[2]
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| Names | |
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| Preferred IUPAC name
1-Bromo-4-iodobenzene | |
| Other names
p-Bromoiodobenzene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.008.785 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H4BrI | |
| Molar mass | 282.90 g/mol |
| Appearance | colorless solid |
| Melting point | 91 °C (196 °F; 364 K)[1] |
| Related compounds | |
Related compounds |
1,4-Dibromobenzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
In one laboratory route to 1-bromo-4-iodobenzene, 4-bromoaniline is treated with concentrated sulfuric acid and sodium nitrite to form the diazonium salt, which is then treated with potassium iodide to form 1-bromo-4-iodobenzene.[3]
Reactions
Since aryl iodides are more reactive than aryl bromides in the Sonogashira coupling,[4] the iodine end of 1-bromo-4-iodobenzene can be selectively coupled to a terminal acetylene while leaving the bromine end unreacted, by running the reaction at room temperature. For example, two equivalents of 1-bromo-4-iodobenzene can couple to trimethylsilylacetylene in a room temperature symmetrical Sonogashira coupling (with TMSA being deprotected to acetylene in-situ) to form bis(4-bromophenyl)acetylene.[5]
