ChemicalBook > CAS DataBase List > [Bis(trifluoroacetoxy)iodo]benzene

[Bis(trifluoroacetoxy)iodo]benzene

Product Name: [Bis(trifluoroacetoxy)iodo]benzene
CAS No.: 2712-78-9
Chemical Name: [Bis(trifluoroacetoxy)iodo]benzene
Synonyms: PIFA;BTI;DFAIB;Bacillus thuringiensis israelensis;[Bis(trifluoroacetox;LABOTEST-BB LT00454809;uoroacetoxy)iodo]benzene;[Bis(trifluoroacetoxy)iodo]ben;1Bis-trifluoroacetoxyiodobenzene;IODOBENZENE BIS(TRIFLUOROACETATE)
CBNumber: CB9419191
Molecular Formula: C10H5F6IO4
Formula Weight: 430.04
MOL File: 2712-78-9.mol

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[Bis(trifluoroacetoxy)iodo]benzene Property

Melting point:: 121-125 °C(lit.)
storage temp.: Keep in dark place,Inert atmosphere,2-8°C
solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
form: Crystalline Powder
color: White to pale yellow
Water Solubility: insoluble
Sensitive: Moisture & Light Sensitive
BRN: 764767
Stability:: Air and Moisture Sensitive
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
InChIKey: PEZNEXFPRSOYPL-UHFFFAOYSA-N
SMILES: I(C1C=CC=CC=1)(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F
CAS DataBase Reference: 2712-78-9(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36-37/39
WGK Germany: 3
F: 4.10-8-9-21
Hazard Note: Irritant/Keep Cold
HazardClass: IRRITANT, KEEP COLD, LIGHT SENSITIVE
HS Code: 29036990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 15230
Product name: [Bis(trifluoroacetoxy)iodo]benzene
Purity: purum, ≥95.0% (AT)
Packaging: 10g
Price: $94
Updated: 2025/07/31

Sigma-Aldrich

Product number: 15230
Product name: [Bis(trifluoroacetoxy)iodo]benzene
Purity: purum, ≥95.0% (AT)
Packaging: 50g
Price: $206
Updated: 2025/07/31

Sigma-Aldrich

Product number: 232130
Product name: [Bis(trifluoroacetoxy)iodo]benzene
Purity: 97%
Packaging: 10g
Price: $94.7
Updated: 2025/07/31

Sigma-Aldrich

Product number: 232130
Product name: [Bis(trifluoroacetoxy)iodo]benzene
Purity: 97%
Packaging: 50g
Price: $257
Updated: 2025/07/31

TRC

Product number: B586600
Product name: [Bis(trifluoroacetoxy)iodo]benzene
Packaging: 50g
Price: $195
Updated: 2021/12/16

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[Bis(trifluoroacetoxy)iodo]benzene Chemical Properties,Usage,Production

Chemical Properties

White to pale yellow crystalline powder

Uses

[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.

Uses

In oxidation, cyclization, dehydrogenation, and dearomatization reactions.

reaction suitability

reagent type: oxidant

Synthesis

591-50-4

76-05-1

2712-78-9

Under an argon atmosphere (protected with an argon balloon), iodobenzene (28 mL, 250 mmol) was added to the reaction vessel, followed by trifluoroacetic acid (TFA, 100 mL) and chloroform (CHCl3, 240 mL). Oxone (116 g, 377 mmol, 1.5 eq.) was added slowly under vigorous stirring conditions. Immediately after the addition, the reaction mixture was cooled in an ice bath for 30 min due to the exothermic nature of the reaction. After removal of the ice bath, the reaction mixture was stirred continuously at room temperature for 48 hours. Upon completion of the reaction, the solid was suspended in chloroform and separated by filtration. The filtrate was concentrated to dryness under reduced pressure to afford [bis(trifluoroacetoxy)iodo]benzene as an off-white solid (89.3 g, 208 mmol, 83% yield). The product was characterized by 1H NMR (300 MHz, chloroform-d): δ 8.20 (d, J = 7.8 Hz, 2H), 7.74 (t, J = 7.4 Hz, 1H), 7.62 (t, J = 7.8 Hz, 2H).

Purification Methods

Crystallise the iodo compound from warm trifluoroacetic acid and dry it over NaOH pellets. Recrystallise it also from Me2CO/pet ether. Its melting point depends on the heating rate. [Spyroudis & Varvoglis Synthesis 445 1975, application: Almond et al. Org Synth 66 132 1988.]

References

[1] Journal of Organic Chemistry, 2010, vol. 75, # 6, p. 2119 - 2122
[2] Patent: WO2018/106112, 2018, A1. Location in patent: Page/Page column 67
[3] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 1, p. 142 - 144
[4] Nature Chemistry, 2018, vol. 10, # 2, p. 200 - 204
[5] Russian Journal of General Chemistry, 1994, vol. 64, # 12.2, p. 1826

[Bis(trifluoroacetoxy)iodo]benzene Preparation Products And Raw materials

Raw materials

Iodobenzene Hexane Hydrogen peroxide Sodium percarbonate Trifluoroacetic anhydride Dichloromethane

Preparation Products

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View Lastest Price from [Bis(trifluoroacetoxy)iodo]benzene manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: [Bis(trifluoroacetoxy)iodo]benzene 2712-78-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%min
Supply Ability: 30tons/month
Release date: 2023-01-31

Henan Aochuang Chemical Co.,Ltd.

Product: [Bis(trifluoroacetoxy)iodo]benzene 2712-78-9
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-10-09

Shanghai UCHEM Inc.

Product: [Bis(trifluoroacetoxy)iodo]benzene 2712-78-9
Price: US $8.00-129.00/g
Min. Order: 25g
Purity: 0.98
Supply Ability: 25kg
Release date: 2023-12-14

2712-78-9, [Bis(trifluoroacetoxy)iodo]benzeneRelated Search:

(Trifluoromethoxy)benzene Iodine Ethylbenzene Anisole Allylbenzene Sodium triacetoxyborohydride (Diacetoxyiodo)benzene Acetoxyacetic acid Acetoxyacetyl chloride Povidone iodine 2-Phenoxyethanol Sliver bis(trifluoromethane sulfonimide) Cobalt bis(trifluoroMethylsulfonyl)iMide Silicon tetraacetate Benzene BIS(DICYCLOHEXYLPHOSPHINO)METHANE Bis(dibenzylideneacetone)palladium Bis(2-dicyclohexylphosphinophenyl)ether, 98%

IODOSOBENZENE I,I-BIS(TRIFLUOROACETATE)

IODINE, PHENYLBIS(TRIFLUOROACETATO)-

IODOBENZENE BIS(TRIFLUOROACETATE)

IODOBENZENE I,I-BIS(TRIFLUOROACETATE)

BTI

BIS(TRIFLUORACETOXY)- IODOBENZENE

[BIS(TRIFLUOROACETOXY)IODO]BENZENE

[Bis(trifluoroacetoxy)](phenyl)iodane

[Bis(trifluoroacetoxy)iodo]ben

Iodobenzene 1,1-bis(trifluoroacetate)

[Bis(trifluoroacetoxy)iodo]benzene purum, >=95.0% (AT)

[Bis(trifluoroacetoxy)iodo]benzene SynonyMs Phenylbis(trifluoroacetato-O)iodine

[phenyl-(2,2,2-trifluoroacetyl)oxy-3-iodanyl] 2,2,2-trifluoroacetate

[phenyl-(2,2,2-trifluoroacetyl)oxy-λ<sup>3</sup>-iodanyl] 2,2,2-trifluoroacetate

uoroacetoxy)iodo]benzene

PIFA

BTI~Iodosobenzene bis(trifluoroacetate)~Phenyliodine(III) bis(trifluoroacetate)~PIFA

phenylbis(trifluoroacetato-O)iodine

Bis-Trifluoroacetoxyiodobenzene99%

Bis-Trifluoroacetoxyiodobenzene 99%

Iodosobenzene-bis(trifluoroacetate)

Phenyliodine(III)bis(trifluoroacetate)

Bis(trifluoroacetoxy)iodoübenzene, 97%

BTI, Iodobenzene I,I-bis(trifluoroacetate), PIFA

[Bis(trifluoroacetoxy)iodo(III)]benzene

[Di(trifluoroacetoxy)iodo(III)]benzene

Bis(trifluoroacetic acid)phenyliodine(III) salt

Phenylbis(trifluoroacetyloxy) iodine(III)

Iodine, phenylbis(trifluoroacetato-.kappa.O)-

bis(I,I-trifluoroacetoxy)iodobenzene

[Bis(trifluoroacetoxy)iodo]benzene,98%

1Bis-trifluoroacetoxyiodobenzene

[Bis(trifluoroethoxy)iodo]benzene

[Bis(trifluoroacetoxy)iodo]benzene,BTI, Iodobenzene I,I-bis(trifluoroacetate), PIFA

[Bis(trifluoroacetox

[Bis(trifluoroacetoxy)iodo]benzene, 98% 10GR

[Bis(trifluoroacetoxy)iodo]benzene, 98% 50GR

LABOTEST-BB LT00454809

DFAIB

BIS(TRIFLUOROACETOXY)IODOBENZENE FOR SYN

[Bis(trifluoroacetoxy)iodo]benzene, 98%, for synthesis

[Bis(trifluoroacetoxy)iodo]benzene &gt

Iodine, phenylbis(2,2,2-trifluoroacetato-κO)-

[Bis(trifluoroacetoxy)iodo]benzene ISO 9001：2015 REACH

Bacillus thuringiensis israelensis

[phenyl-(2,2,2-trifluoroacetyl)oxy-

[Bis(trifluoroacetoxy)iodo]benzene, 97%

Di (trifluoroacetoxy) iodobenzene

[Bis(trifluoroacetyloxy)iodo]benzene

2712-78-9

C10H3F6IO4

C10H5F6IO4

C10H5O4F6I

CF3CO22IC6H5

C10F6H5I1O4

C10H9F6IO2

Oxidation

Synthetic Reagents