(bis(trifluoroacetoxy)iodo)benzene

(Bis(trifluoroacetoxy)iodo)benzene

Names
Other names Phenyliodine bis(trifluoroacetate); PIFA
Identifiers
CAS Number	2712-78-9 N
3D model (JSmol)	Interactive image
ChemSpider	92428 Y
ECHA InfoCard	100.018.462
PubChem CID	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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

(Bis(trifluoroacetoxy)iodo)benzene, C
6H
5I(OCOCF
3)
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.

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:

It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid:

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.

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.