(Bis(trifluoroacetoxy)iodo)benzene
Names | |
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Preferred IUPAC name
Phenyl-λ3-iodanediyl bis(trifluoroacetate) | |
Other names
Phenyliodine bis(trifluoroacetate); PIFA
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.018.462 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H5F6IO4 | |
Molar mass | 430.041 g·mol−1 |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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(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.[1]
Preparation
The syntheses of all aryl
(diacetoxyiodo)benzene:[1]
It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid:[2]
Uses
It also brings around the conversion of a
carbonyl
compounds.
Hofmann rearrangement
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.
References
- ^ ISBN 9780080977430.
- ^ ; Collected Volumes, vol. 8, p. 132.
- .
- ISBN 9781483258683.