Di-t-butyl Dicarbonate

[24424-99-5] C10H18O5 (MW 218.25) InChI = 1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3 InChIKey = DYHSDKLCOJIUFX-UHFFFAOYSA-N (efficient tert-butoxycarbonylating agent for amines,1, 2 phenols, and thiols; tert-butoxycarbonylation of alcohols, amides,3 lactams, carbamates4 and NH-pyrroles5 occurs in the presence of 4-dimethylaminopyridine) Alternate Names: di-tert-butyl pyrocarbonate; Boc anhydride; Boc2O. Physical Data: mp 22–24 °C; bp 56–57 °C/0.5 mm Hg; fp 37 °C; d 0.950 g cm−3; nD20 1.4103. Solubility: insol cold H2O; sol most organic solvents such as decalin, toluene, CCl4, THF, dioxane, alcohols, acetone, MeCN, DMF. Form Supplied in: colorless liquid; widely available. Analysis of Reagent Purity: IR 1810 and 1765 cm−1; NMR 1.50 (CCl4). Preparative Method: prepared by the action of Phosgene on potassium tert-butyl carbonate, followed by conversion of the obtained di-tert-butyl tricarbonate under the action of basic catalysts such as 1,4-Diazabicyclo[2.2.2]octane.6 Handling, Storage, and Precautions: the liquid is flammable and must be stored in a refrigerator in the absence of moisture. Do not heat above 80 °C.