Names | |
---|---|
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 |
EC Number |
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PubChem
CID
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UNII | |
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).
|
1-Bromo-4-iodobenzene is a mixed aryl halide ( aryl bromide and aryl iodide) with the formula BrC6H4I. [2]
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]
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]
Names | |
---|---|
Preferred IUPAC name
1-Bromo-4-iodobenzene | |
Other names
p-Bromoiodobenzene
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.008.785 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
1-Bromo-4-iodobenzene is a mixed aryl halide ( aryl bromide and aryl iodide) with the formula BrC6H4I. [2]
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]
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]