(Bis (trifluoroacetoxy) iodine) benzene

Structural formula
General
Surname	[Bis (trifluoroacetoxy) iodine] benzene
other names	Phenyl iodine (III) bis (trifluoroacetate); PIFA; BTI;
Molecular formula	C 10 H 5 F 6 IO 4
Brief description	colorless solid
External identifiers / databases
EC number	220-308-0
ECHA InfoCard	100.018.462
PubChem	102317
Wikidata	Q158535
properties
Molar mass	430.04 g mol −1
Physical state	firmly
Melting point	121-124 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 302 + 352-304 + 340-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

[Bis (trifluoroacetoxy) iodine] benzene or phenyl iodine (III) bis (trifluoroacetate) (abbreviated PIFA ) is a hypervalent iodobenzene compound. It is used as reagent in the Hofmann rearrangement in the production of amines from amides with loss of a carbon - atom used.

The reagent can also be used to prepare diazo compounds from hydrazones .

Manufacturing

As with all hypervalent iodobenzenes, the starting compound for the synthesis is iodobenzene . PIFA is made by reacting iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid.

Individual evidence

↑ Data sheet [Bis (trifluoroacetoxy) iodo] benzene 97% Template: Linktext-Check / Escaped from Sigma-Aldrich , accessed on January 22, 2012 ( PDF ).
↑ ^a ^b ^c data sheet bis (trifluoroacetoxy) iodobenzene (PDF) from Merck , accessed on August 31, 2011.
↑ Almond, MR; Stimmel, JB; Thompson, EA; Loudon, GM: Hofmann Rearrangement under mildly acidic Conditions using (I, I-bis (Trifluoroacetoxy)) iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide In: Organic Syntheses . 66, 1988, p. 132, doi : 10.15227 / orgsyn.066.0132 ; Coll. Vol. 8, 1993, p. 132 ( PDF ).

[Aldrich-1] Data sheet [Bis (trifluoroacetoxy) iodo] benzene 97% Template: Linktext-Check / Escaped from Sigma-Aldrich , accessed on January 22, 2012 ( PDF ).

[Merck-2] ta sheet bis (trifluoroacetoxy) iodobenzene (PDF) from Merck , accessed on August 31, 2011.

[3] Almond, MR; Stimmel, JB; Thompson, EA; Loudon, GM: Hofmann Rearrangement under mildly acidic Conditions using (I, I-bis (Trifluoroacetoxy)) iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide In: Organic Syntheses . 66, 1988, p. 132, doi : 10.15227 / orgsyn.066.0132 ; Coll. Vol. 8, 1993, p. 132 ( PDF ).