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• W2107859137 abstract "Trimethylsilyl Ethynyl Benziodoxolone (TMS-EBX) [181934-29-2] C12H13IO2Si (MW 344.22) InChI = 1S/C12H13IO2Si/c1-16(2,3)9-8-13-11-7-5-4-6-10(11)12(14)15-13/h4-7H,1-3H3 InChIKey = KUCCHAADRXRBFZ-UHFFFAOYSA-N (reagent used as electrophilic source of TMS-protected and free acetylene) Physical Data: mp (Dec.) 143–145 °C. Solubility: sol. chlorinated solvents, acetone, DMF, DMSO; moderately sol. THF, acetonitrile, alcohols, toluene, xylene; not sol. hexane, ethers. Form Supplied in: colorless crystals; not available commercially. Analysis of Reagent Purity: purity is analyzed by 1H NMR (400 MHz, CDCl3) δ 8.42 (dd, J = 6.4, 1.9 Hz, 1H; ArH), 8.19 (m, 1H; ArH), 7.78 (m, 2H; ArH), 0.32 (s, 9H; Si(CH3)) and 13C NMR (100 MHz, CDCl3) δ 166.4, 134.9, 132.6, 131.7, 131.4, 126.1, 117.2, 115.4, 64.2, −0.5. Preparative Methods: 1, 2 Oxidation of the commercially available 2-iodobenzoic acid with sodium periodate affords 2-iodosyl benzoic acid (1-hydroxy-1,2-benziodoxol-3(1H)-one) (eq 1). The latter is then activated by treatment with freshly distilled trimethylsilyl triflate and reacted in situ with bis(trimethylsilyl)acetylene (eq 2). Large quantities (up to 24 g) may be prepared and stored in a refrigerator. Due to the potential exothermic decomposition associated with high-energy hypervalent compounds, these reactions have to be conducted behind a safety shield. (1) (2) Purification: TMS-EBX can be efficiently purified by recrystallization from acetonitrile. Handling, Storage, and Precautions: the reagent is stable to air, moisture, and light. Prolonged exposure to light and higher temperature may cause decomposition (CAUTION: an exothermic degradation was observed by DSC at 117–181 °C (596 J g−1) and it is advised to run reactions with TMS-EBX below 17 °C). For long time storage the reagent should be protected from light in a refrigerator. Its specific toxicity has not been reported to date. TMS-EBX is incompatible with hard nucleophiles, strong bases, and reducing agents. Treatment with desilylating agents, especially fluoride sources, causes decomposition at room temperature. Triisopropylsilyl Ethynyl Benziodoxolone (TIPS-EBX) [181934-30-5] C18H25IO2Si (MW 428.38) InChI = 1S/C18H25IO2Si/c1-13(2)22(14(3)4,15(5)6)12-11-19-17-10-8-7-9-16(17)18(20)21-19/h7-10,13-15 H,1-6H3 InChIKey = NTHGHMCOPNSZIR-UHFFFAOYSA-N (reagent used as electrophilic source of TIPS-protected acetylene) Physical data: mp (Dec.) 170–176 °C. Solubility: sol. chlorinated solvents, alcohols, DMF, DMSO; moderately sol. ethers, acetonitrile; not sol. toluene, hexane. Form supplied in: colorless crystals, available from Sigma–Aldrich. Analysis of Reagent Purity: purity is analyzed by 1H NMR (400 MHz, CDCl3) δ 8.44 (m, 1H; ArH), 8.29 (m, 1H; ArH), 7.77 (m, 2H; ArH), 1.16 (m, 21H; Si(CH(CH3)2)3) and 13C NMR (100 MHz, CDCl3) δ 166.4, 134.6, 132.3, 131.4, 131.4, 126.1, 115.6, 114.1, 64.6, 18.4, 11.1. Preparative Method: 2, 3 2-iodosyl benzoic acid (see TMS-EBX section for details) is activated by treatment with freshly distilled trimethyl silyl triflate and reacted in situ with (trimethylsilyl)(triiso-propylsilyl)acetylene (eq 3). Large quantities (up to 30 g) may be prepared and stored in a refrigerator. Due to the potential exothermic decomposition associated with high-energy hypervalent compounds, this reaction has to be conducted behind a safety shield. (3) Purification: the TIPS-EBX reagent can be efficiently purified by recrystallization from acetonitrile. Handling, Storage, and Precautions: the reagent is stable to air, moisture, and light. Possible decomposition on prolonged exposure to light and high temperature (CAUTION: an exothermic degradation was observed by DSC at 135–174 °C (36 J g−1) and 175–245 °C (496 J g−1) and it is advised to run reactions with TIPS-EBX below 35 °C). For long time storage the reagent should be protected from light in a refrigerator. Its specific toxicity has not been reported up to date. TIPS-EBX is incompatible with hard nucleophiles, strong bases, and reducing agents. Treatment with desilylating agents, especially fluoride sources, causes slow decomposition at room temperature. When compared with TMS-EBX, TIPS-EBX displayed significantly enhanced stability towards nucleophiles and thermal decomposition." @default.
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• W2107859137 date "2012-09-14" @default.
• W2107859137 modified "2023-10-05" @default.
• W2107859137 title "Silyl Ethynyl Benziodoxolone Reagents" @default.
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