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| | [Bis(trifluoroacetoxy)iodo]benzene Basic information |
| Product Name: | [Bis(trifluoroacetoxy)iodo]benzene | | Synonyms: | 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 | | CAS: | 2712-78-9 | | MF: | C10H5F6IO4 | | MW: | 430.04 | | EINECS: | 220-308-0 | | Product Categories: | Carbazoles | | Mol File: | 2712-78-9.mol | ![[Bis(trifluoroacetoxy)iodo]benzene Structure](CAS/GIF/2712-78-9.gif) |
| | [Bis(trifluoroacetoxy)iodo]benzene Chemical Properties |
| 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) |
| 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 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | [Bis(trifluoroacetoxy)iodo]benzene Usage And Synthesis |
| Chemical Properties | White to pale yellow crystalline powder | | Uses | In oxidation, cyclization, dehydrogenation, and dearomatization reactions. | | 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. | | 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 |
| | [Bis(trifluoroacetoxy)iodo]benzene Preparation Products And Raw materials |
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