1-Bromo-4-iodobenzene

1-Bromo-4-iodobenzene
Names
Preferred IUPAC name
1-Bromo-4-iodobenzene
Other names
p-Bromoiodobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.785 Edit this at Wikidata
EC Number
  • 209-662-7
UNII
  • InChI=InChI = 1S/C6H4BrI/c7-5-1-3-6(8)4-2-5/h1-4H checkY
    Key: UCCUXODGPMAHRL-UHFFFAOYSA-N checkY
  • C1=CC(=CC=C1Br)I
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]

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]

Symmetrical Sonogashira coupling of 1-bromo-4-iodobenzene with trimethylsilylacetylene with in situ TMSA deprotection.

See also

References

  1. ^ "1-Bromo-4-iodobenzene". ChemSpider. Retrieved 21 October 2023.
  2. ^ PubChem. "1-Bromo-4-iodobenzene". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-22.
  3. ^ Banerjee, M.; Shukla, R.; Rathore, R. (15 January 2009). "Synthesis, Optical, and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires". Journal of the American Chemical Society. 131 (5): 1780–1786. doi:10.1021/ja805102d. PMID 19146375.
  4. ^ Chinchilla, R.; Nájera, C. (2007), "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry", Chem. Rev., 107 (3): 874–922, doi:10.1021/cr050992x, PMID 17305399
  5. ^ Mio, Matthew J.; Kopel, Lucas C.; Braun, Julia B.; Gadzikwa, Tendai L.; Hull, Kami L.; Brisbois, Ronald G.; Markworth, Christopher J.; Grieco, Paul A. (2002). "One-Pot Synthesis of Symmetrical and Unsymmetrical Bisarylethynes by a Modification of the Sonogashira Coupling Reaction". Organic Letters. 4 (19): 3199–3202. doi:10.1021/ol026266n. PMID 12227748.