Available from stock

(Bis(trifluoroacetoxy)iodo)benzene

SKU: T0620

Category: Building Blocks, Intermediates, Reagents

Synonyms: BTIB, PIFA, Phenyliodine bis(trifluoroacetate); 2712-78-9
CAS-Number: C₁₀H₅F₆IO₄
Molecular Formula: 430.04
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (AT)
Appearance: Colorless ro whit powder or crystals

Properties

Solvents: Soluble in chloroform.
Melting Point: 121-125 °C (lit.)

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H315 - H319 - H335
Precautionary statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
GHS Symbol: GHS07
Signal word: Warning
Transportation: Not dangerous goods

Description: (Bis(trifluoroacetoxy)iodo)benzene (BTIB; PIFA) is a hypervalent iodine reagent widely used as a mild and selective oxidizing agent in organic synthesis. It facilitates oxidative transformations such as phenol coupling, dearomatization, α-oxygenation of carbonyl compounds, and heterocycle formation under mild conditions, often avoiding harsh metal-based oxidants. (Bis(trifluoroacetoxy)iodo)benzene is also employed in peptide and carbohydrate chemistry for oxidative cleavage and functionalization of sensitive substrates.
Smiles: O=C(C(F)(F)F)OI(OC(C(F)(F)F)=O)C1=CC=CC=C1
InChi Key: PEZNEXFPRSOYPL-UHFFFAOYSA-N
References: (1) P.V. Pallai, et al.; Int. J. Pept. Protein Res. 21, 84 (1983) , (2) P.V. Pallai, et al.; Biochemistry 24, 1933 (1985) , (3) M. Catir, et al.; J. Org. Chem. 74, 4560 (2009) , (4) D. Kumar, et al.; Bioorg. Med. Chem. Lett. 19, 4492 (2009) , (5) N. Chatterjee, et al.; Org. Biomol. Chem. 13, 4828 (2015) , (6) T. Imai, et al.; J. Org. Chem. 81, 3975 (2016) , (7) Y. Wan, et al.; J. Org. Chem. 84, 780 (2019) , (8) C. Mudithanapelli, et al.; Org. Lett. 21, 3098 (2019) , (9) C. Mudithanapelli & M.H. Kim; Org. Biomol. Chem. 18, 450 (2020) , (10) X.T. Sun, et al.; Molecules 27, 726 (2022) , (11) Y. Matsuo, et al.; Angew. Chem. Int. Ed. Engl. 62, e202314968 (2023)
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

(Bis(trifluoroacetoxy)iodo)benzene (BTIB; PIFA) is a hypervalent iodine reagent widely used as a mild and selective oxidizing agent in organic synthesis. It facilitates oxidative transformations such as phenol coupling, dearomatization, α-oxygenation of carbonyl compounds, and heterocycle formation under mild conditions, often avoiding harsh metal-based oxidants. (Bis(trifluoroacetoxy)iodo)benzene is also employed in peptide and carbohydrate chemistry for oxidative cleavage and functionalization of sensitive substrates.

SKU: T0620 Category: Building Blocks, Intermediates, Reagents

Additional information

Additional information

Synonyms	BTIB, PIFA, Phenyliodine bis(trifluoroacetate)
Purity	≥95% (AT)
Appearance	Colorless ro whit powder or crystals
CAS-Number	2712-78-9
Molecular Formula	C10H5F6IO4
Molecular Weight	430.04
Solvents	Soluble in chloroform.
Melting Point	121-125 °C (lit.)
Smiles	O=C(C(F)(F)F)OI(OC(C(F)(F)F)=O)C1=CC=CC=C1
InChi Key	PEZNEXFPRSOYPL-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H315 – H319 – H335
Precautionary statements	P261 – P264 – P271 – P280 – P302 + P352 – P305 + P351 + P338
GHS Symbol	GHS07
Signal word	Warning
Transportation	Not dangerous goods
References	(1) P.V. Pallai, et al.; Int. J. Pept. Protein Res. 21, 84 (1983), (2) P.V. Pallai, et al.; Biochemistry 24, 1933 (1985), (3) M. Catir, et al.; J. Org. Chem. 74, 4560 (2009), (4) D. Kumar, et al.; Bioorg. Med. Chem. Lett. 19, 4492 (2009), (5) N. Chatterjee, et al.; Org. Biomol. Chem. 13, 4828 (2015), (6) T. Imai, et al.; J. Org. Chem. 81, 3975 (2016), (7) Y. Wan, et al.; J. Org. Chem. 84, 780 (2019), (8) C. Mudithanapelli, et al.; Org. Lett. 21, 3098 (2019), (9) C. Mudithanapelli & M.H. Kim; Org. Biomol. Chem. 18, 450 (2020), (10) X.T. Sun, et al.; Molecules 27, 726 (2022), (11) Y. Matsuo, et al.; Angew. Chem. Int. Ed. Engl. 62, e202314968 (2023)
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
Quantity	10 g, 50 g, Bulk