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2712-78-9 - [Bis(trifluoroacetoxy)iodo]benzene, 97% - BTI - Iodosobenzene bis(trifluoroacetate) - L15141 - Alfa Aesar

L15141 [Bis(trifluoroacetoxy)iodo]benzene, 97%

Numéro CAS
2712-78-9
Synonymes
BTI
Iodosobenzene bis(trifluoroacetate)

Dimensions Prix ($) Quantité Disponibilité
5g 34,00
25g 91,60
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[Bis(trifluoroacetoxy)iodo]benzene, 97%

MDL
MFCD00009672
EINECS
220-308-0

Propriétés chimiques

Formule
C10H5F6IO4
Poids formulaire
430.04
Point de fusion
122-125°
Sensibilité
Moisture & Light Sensitive
Solubilité
Insoluble in water.

Applications

[Bis(trifluoroacetoxy)iodo]benzene acts as a reagent in Pummerer-like reactions. It plays an important role in the direct alfa-hydroxylation of ketones under acidic conditions. It is involved in the cyclization of styryl amines to N-alkyl or N-aryl indoles. It serves as a reagent for the chemoselective deprotection of dimethoxybenzyl ethers and tosyloxylation of anilides. Further, it is used in the synthesis of 1,3,4-oxadiazoles by the oxidation of N-acylhydrazones. In addition to this, it is employed in the Hofmann rearrangement for the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.

Notes

Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases.

Références bibliographiques

Hypervalent iodine oxidizing agent, cf Iodosobenzene diacetate, B24531. PIFA oxidizes hydroquinones and catechols to benzoquinones. In the presence of a nucleophile, 4-substituted phenols give the corresponding 4,4-disubstituted cyclohexadienone: J. Chem. Soc., Perkin 1, 1891 (1993); 2047 (1994), and refs. therein. In water, 1,4-dimethoxy aromatics undergo oxidative demethylation to p-quinones: Tetrahedron Lett., 42, 6899 (2001). In TFA, acetanilides can be hydroxylated in the p-position: J. Org. Chem., 67, 7424 (2002).

Terminal alkynes are oxidized by PIFA to ɑ-hydroxy ketones: Tetrahedron Lett., 26, 3837 (1985).

Primary amides undergo a Hofmann-like rearrangement to amines, avoiding the harsh conditions often required for the classical method: J. Org. Chem., 49, 4272, 4277 (1984); Synth. Commun., 18, 1615 (1988); Org. Synth. Coll., 8, 132 (1993). Promotes the azidation of alkyl groups of p-alkylanisoles with TMS azide: Tetrahedron Lett., 32, 4321 (1991); J. Am. Chem. Soc., 116, 3684 (1994); Synlett, 427 (1994), and also the direct nucleophilic sulfenylation and thiocyanation of phenol ethers with thiols and TMS isothiocyanate respectively: Synlett, 211 (1995); J. Org. Chem., 60, 7144 (1995).

Mediates the selective cyanation of electron-rich aromatics with Trimethyl­silyl­ cyanide, A19598, e.g. indoles to 2-cyanoindoles: Org. Lett., 7, 537 (2005).

For a brief feature on uses of this reagent in synthesis, see: Synlett, 2851 (2006). For a comprehensive review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).

Chatterjee, N.; Bhatt, D.; Goswami, A. A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids. Org. Biomol. Chem. 2015, 13 (17), 4828-4832.

Chatterjee, N.; Goswami, A. Metal and base free synthesis of primary amines via ipso amination of organoboronic acids mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). Org. Biomol. Chem. 2015, 13 (29), 7940-7945.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
764767
Code tarifaire harmonisé
2915.90
TSCA
No

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