Description

(Bis(trifluoroacetoxy)iodo)benzene (CAS No. 2712-78-9) is a highly reactive hypervalent iodine reagent with the molecular formula C₁₀H₅F₆IO₄. This compound, also known by its IUPAC name [phenyl-(2,2,2-trifluoroacetyl)oxy-lambda3-iodanyl] 2,2,2-trifluoroacetate, is a versatile oxidizing agent widely used in organic synthesis. It features two trifluoroacetoxy groups bound to a central iodine atom, which is further attached to a phenyl ring, providing exceptional reactivity in electrophilic substitutions and oxidative transformations. The trifluoroacetate groups enhance its stability and solubility in organic solvents, making it ideal for laboratory-scale reactions. This reagent is supplied as a high-purity crystalline solid, ensuring consistent performance in demanding synthetic applications. Store in a cool, dry place away from light and moisture to maintain its efficacy.

Properties

• CAS Number: 2712-78-9
• Complexity: 360
• IUPAC Name: [phenyl-(2,2,2-trifluoroacetyl)oxy-lambda3-iodanyl] 2,2,2-trifluoroacetate
• 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
• InChI Key: PEZNEXFPRSOYPL-UHFFFAOYSA-N
• Exact Mass: 429.91368
• Molecular Formula: C10H5F6IO4
• Molecular Weight: 430.04
• SMILES: C1=CC=C(C=C1)I(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F
• Topological: 52.6
• Monoisotopic Mass: 429.91368
• Synonyms: [Bis(trifluoroacetoxy)iodo]benzene, 2712-78-9, (Bis(trifluoroacetoxy)iodo)benzene, BIS(TRIFLUOROACETOXY)IODOBENZENE, Bis(I,I-trifluoroacetoxy)iodobenzene, UNII-659SFV27XS, 659SFV27XS, iodobenzene bis(trifluoroacetate), phenyliodine bis(trifluoroacetate), I,I-bis(trifluoroacetoxy)iodobenzene, EINECS 220-308-0, phenyliodine(III) bis(trifluoroacetate), DTXSID40181584, IODOBENZENE DI(TRIFLUOROACETATE), BIS(TRIFLUOROACETATO)PHENYL IODIDE, PHENYLIODOSO BIS(TRIFLUOROACETATE), BIS(TRIFLUOROACETATO)(PHENYL)IODINE, BENZENE, (BIS(TRIFLUOROACETOXY)IODO)-, PHENYLBIS(TRIFLUOROACETATO-.KAPPA.O)IODINE, PHENYLIODINE(III) BIS(TRIFLUOROACETATE) [MI], PHENYLBIS(2,2,2-TRIFLUOROACETATO-.KAPPA.O)IODINE, PIFA cpd, TAIB cpd, BIITFAIB, DTXCID80104075, PHENYLBIS(TRIFLUOROACETATO-KAPPAO)IODINE, PHENYLBIS(2,2,2-TRIFLUOROACETATO-KAPPAO)IODINE, 6-Iodonio-2,4-cyclohexadienylium bis(trifluoroacetate), 220-308-0, PIFA, MFCD00009672, Iodine, phenylbis(trifluoroacetato-O)-, [phenyl-(2,2,2-trifluoroacetyl)oxy-lambda3-iodanyl] 2,2,2-trifluoroacetate, Iodobenzene I,I-bis(trifluoroacetate), BTI, Phenylbis(trifluoroacetato-O)iodine, bis-trifluoroacetoxyiodobenzene, iodophenyl(2,2,2-trifluoroacetyloxy)methyl 2,2,2-trifluoroacetate, PhI(OCOCF3)2, Iodine, phenylbis(trifluoroacetato-.kappa.O)-, SCHEMBL57095, Bis(trifluoroacetoxy)phenyl iodine, [bis(trifluoroacetoxyl)iodo]benzene, [bis(trifluoro-acetoxy)iodo]benzene, [bis(trifluoroacetoxy) iodo]benzene, [bis(trifluoroacetoxy)-iodo]benzene, [bis(trifluoroacetoxy)iodo] benzene, [bis(trifluoroacetoxyl)-iodo]benzene, I,I-bis(trifluoroacetate)iodobenzene, [bis-(trifluoroacetoxy) iodo]benzene, SBB057936, I,I-bis-(trifluoroacetoxy)iodobenzene, AKOS005146009, AB00978, AC-3051, CS-W011628, FB49107, [Bis(trifluoroacetoxy)iodo]benzene, 97%, Phenylbis(trifluoroacetato-O)iodine; BTI, AS-14346, DB-005042, A5291, B1175, NS00124319, ST51007256, EN300-179189, I11501, Iodine, phenylbis[(2,2,2-trifluoroacetyl)oxy]-, Q158535, Phenyl[bis(2,2,2-trifluoroacetoxy)]-lambda3-iodane, [Bis(trifluoroacetoxy)iodo]benzene, purum, >=95.0% (AT), phenyl[(2,2,2-trifluoroacetyl)oxy]-lambda3-iodanyl 2,2,2-trifluoroacetate

Application

(Bis(trifluoroacetoxy)iodo)benzene is a powerful hypervalent iodine reagent used for oxidative functionalization of organic substrates, including the conversion of alcohols to carbonyl compounds and the oxidative coupling of phenols. It is particularly valuable in the synthesis of heterocyclic compounds and the introduction of trifluoroacetoxy groups into aromatic systems. Researchers also employ it for C-H activation and as a mild alternative to heavy metal oxidants in environmentally sensitive applications.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (98%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (98%)

If you are interested or have any questions, please contact us at support@atomfair.com

Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.