[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki19\/bistrifluoroacetoxyiodobenzene-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki19\/bistrifluoroacetoxyiodobenzene-wikipedia\/","headline":"(Bis(trifluoroacetoxy)iodo)benzene – Wikipedia","name":"(Bis(trifluoroacetoxy)iodo)benzene – Wikipedia","description":"From Wikipedia, the free encyclopedia (Bis(trifluoroacetoxy)iodo)\u00adbenzene Names Preferred IUPAC name Phenyl-\u03bb3-iodanediyl bis(trifluoroacetate) Other names Phenyliodine bis(trifluoroacetate); PIFA Identifiers ChemSpider ECHA","datePublished":"2014-04-09","dateModified":"2014-04-09","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki19\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki19\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/4\/42\/%28bis%28trifluoroacetoxy%29iodo%29benzene.png\/150px-%28bis%28trifluoroacetoxy%29iodo%29benzene.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/4\/42\/%28bis%28trifluoroacetoxy%29iodo%29benzene.png\/150px-%28bis%28trifluoroacetoxy%29iodo%29benzene.png","height":"80","width":"150"},"url":"https:\/\/wiki.edu.vn\/en\/wiki19\/bistrifluoroacetoxyiodobenzene-wikipedia\/","wordCount":3142,"articleBody":"From Wikipedia, the free encyclopedia(Bis(trifluoroacetoxy)iodo)\u00adbenzeneNamesPreferred IUPAC namePhenyl-\u03bb3-iodanediyl bis(trifluoroacetate)Other namesPhenyliodine bis(trifluoroacetate); PIFAIdentifiersChemSpiderECHA InfoCard100.018.462 EC NumberUNIIInChI=1S\/C10H5F6IO4\/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16\/h1-5H\u00a0YKey:\u00a0PEZNEXFPRSOYPL-UHFFFAOYSA-N\u00a0YInChI=1\/C10H5F6IO4\/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16\/h1-5HKey:\u00a0PEZNEXFPRSOYPL-UHFFFAOYAAFC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1PropertiesC10H5F6IO4Molar mass430.041\u00a0g\u00b7mol\u22121HazardsGHS labelling:WarningH315, H319, H335P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compound(Bis(trifluoroacetoxy)iodo)benzene, C6H5I(OCOCF3)2, is a hypervalent iodine compound used as a reagent in organic chemistry.  It can be used to carry out the Hofmann rearrangement under acidic conditions.[1]Preparation[edit]The syntheses of all aryl hypervalent iodine compounds start from iodobenzene. The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid in a method analogous to the synthesis of (diacetoxyiodo)benzene:[1]It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid:[2]It also brings around the conversion of a hydrazone to a diazo compound, for example in the diazo-thioketone coupling. It also converts thioacetals to their parent carbonyl compounds.Hofmann rearrangement[edit]The Hofmann rearrangement is a decarbonylation reaction whereby an amide is converted to an amine by way of an isocyanate intermediate. It is usually carried out under strongly basic conditions.[3][4]The reaction can also be carried out under mildly acidic conditions by way of the same intermediate using a hypervalent iodine compound in aqueous solution.[1]  An example published in Organic Syntheses is the conversion of cyclobutanecarboxamide, easily synthesized from cyclobutylcarboxylic acid, to cyclobutylamine.[2] The primary amine is initially present as its trifluoroacetate salt, which can be converted to the hydrochloride salt to facilitate product purification.[1][2]References[edit]^ a b c d Aub\u00e9, Jeffrey; Fehl, Charlie; Liu, Ruzhang; McLeod, Michael C.; Motiwala, Hashim F. (1993). “6.15 Hofmann, Curtius, Schmidt, Lossen, and Related Reactions”. Heteroatom Manipulations. Comprehensive Organic Synthesis II. Vol.\u00a06. pp.\u00a0598\u2013635. doi:10.1016\/B978-0-08-097742-3.00623-6. ISBN\u00a09780080977430.^ a b c Almond, M. R.; Stimmel, J. B.; Thompson, E. A.; Loudon, G. M. (1988). “Hofmann Rearrangement Under Mildly Acidic Conditions Using [I,I-Bis(Trifluoroacetoxy)]Iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide”. Organic Syntheses. 66: 132. doi:10.15227\/orgsyn.066.0132.; Collective Volume, vol.\u00a08, p.\u00a0132^ Wallis, Everett S.; Lane, John F. (1946). “The Hofmann Reaction”. Organic Reactions. 3 (7): 267\u2013306. doi:10.1002\/0471264180.or003.07.^ Surrey, Alexander R. (1961). “Hofmann Reaction”. Name Reactions in Organic Chemistry (2nd\u00a0ed.). Academic Press. pp.\u00a0134\u2013136. ISBN\u00a09781483258683.  "},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki19\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki19\/bistrifluoroacetoxyiodobenzene-wikipedia\/#breadcrumbitem","name":"(Bis(trifluoroacetoxy)iodo)benzene – Wikipedia"}}]}]