1-Bromo-4-iodobenzene

1-Bromo-4-iodobenzene p-Bromoiodobenzene 1-bromo-4-iodobenzene 2.png 200 1-bromo-4-iodobenzene 3D.png 200 1-bromo-4-iodobenzene sample.jpg 150 1-Bromo-4-iodobenzene 589-87-7 correct CAS correct chemspider 11038 209-662-7 11522 correct FDA R9LDG2XS7C C1=CC(=CC=C1Br)I correct chemspider InChI = 1S/C6H4BrI/c7-5-1-3-6(8)4-2-5/h1-4H correct chemspider UCCUXODGPMAHRL-UHFFFAOYSA-N C6H4BrI 282.90 g/mol colorless solid 91 https://www.chemspider.com/Chemical-Structure.11038.html 1-Bromo-4-iodobenzene ChemSpider 21 October 2023 1,4-Dibromobenzene 1-Bromo-4-iodobenzene is a mixed aryl halide (aryl bromide and aryl iodide) with the formula BrC6H4I.PubChem 1-Bromo-4-iodobenzene https://pubchem.ncbi.nlm.nih.gov/compound/1-Bromo-4-iodobenzene 2023-10-22 pubchem.ncbi.nlm.nih.gov en 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.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 10.1021/ja805102d 19146375 Reactions Since aryl iodides are more reactive than aryl bromides in the Sonogashira coupling,Chinchilla, R. Nájera, C. Chem. Rev. The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry 2007 107 3 874–922 10.1021/cr050992x 17305399 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.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 10.1021/ol026266n 12227748 600px|Symmetrical Sonogashira coupling of 1-bromo-4-iodobenzene with trimethylsilylacetylene with in situ TMSA deprotection. See also Bromobenzene Iodobenzene Bromochlorobenzene References Category:Bromobenzene derivatives Category:Iodobenzene derivatives Category:Mixed halobenzenes