(Bis(trifluoroacetoxy)iodo)benzene

(Bis(trifluoroacetoxy)iodo)benzene

Names
Other names Phenyliodine bis(trifluoroacetate); PIFA
Identifiers
CAS Number	2712-78-9 N
ChemSpider	92428 Y
Jmol 3D model	Interactive image
PubChem	102317
InChI InChI=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 Y Key: PEZNEXFPRSOYPL-UHFFFAOYSA-N Y InChI=1/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H Key: PEZNEXFPRSOYPL-UHFFFAOYAA
SMILES FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1
Properties
Chemical formula	C10H5F6IO4
Molar mass	430.04 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

(Bis(trifluoroacetoxy)iodo)benzene, C₁₀H₅F₆IO₄, is a hypervalent iodine compound used as a reagent in organic chemistry. The reagent is used in an acidic modification of the Hofmann rearrangement. One example is the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride. 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.

Preparation

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. The method is analogous to the synthesis of diacetoxyiodobenzene (C₆H₅I(OAc)₂) which uses a mixture of peracetic acid and acetic acid.