| Identification | More | [Name]
[Bis(trifluoroacetoxy)iodo]benzene | [CAS]
2712-78-9 | [Synonyms]
BIS(TRIFLUORACETOXY)-IODOBENZENE
[BIS(TRIFLUOROACETOXY)IODO]BENZENE
BTI
DFAIB
IODINE, PHENYLBIS(TRIFLUOROACETATO)-
IODOBENZENE BIS(TRIFLUOROACETATE)
IODOBENZENE I,I-BIS(TRIFLUOROACETATE)
IODOSOBENZENE I,I-BIS(TRIFLUOROACETATE)
LABOTEST-BB LT00454809
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)
Iodine, phenylbis(trifluoroacetato-.kappa.O)-
bis(I,I-trifluoroacetoxy)iodobenzene
Bis(trifluoroacetoxy)iodoübenzene, 97%
BTI, Iodobenzene I,I-bis(trifluoroacetate), PIFA | [EINECS(EC#)]
220-308-0 | [Molecular Formula]
C10H5F6IO4 | [MDL Number]
MFCD00009672 | [Molecular Weight]
430.04 | [MOL File]
2712-78-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to pale yellow crystalline powder | [Melting point ]
121-125 °C(lit.)
| [storage temp. ]
Keep Cold | [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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
4.10-8-9-21 | [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT, KEEP COLD, LIGHT SENSITIVE | [HS Code ]
29039990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to pale yellow crystalline powder | [Uses]
In oxidation, cyclization, dehydrogenation, and dearomatization reactions. | [reaction suitability]
reagent type: oxidant | [Synthesis]
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 |
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