Diethyl Carbonate

(R = Et) [105-58-8] C5H10O3 (MW 118.13) InChI = 1S/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3 InChIKey = OIFBSDVPJOWBCH-UHFFFAOYSA-N (R = Me) [616-38-6] C3H6O3 (MW 90.08) InChI = 1S/C3H6O3/c1-5-3(4)6-2/h1-2H3 InChIKey = IEJIGPNLZYLLBP-UHFFFAOYSA-N (C-alkoxycarbonylations of carbanions2-12 and other nucleophiles;13 synthesis of ketones14 and tertiary alcohols;15 allylations with allyl alkyl carbonates;16 alkylations of nucleophilic substrates;17-20 heterocyclic synthesis;21 synthesis of dialkyl carbonates;62 synthesis of methyl carbamates;76 protection of 1,2-diols;102 esterification of carboxylic acids;122 methylation of N-H-heterocycles;86 cleavage of N-acyloxazolidinones160) Physical Data: R = Et: bp 127 °C; d 0.975 g cm−3. R = Me: bp 90.3 °C; d 1.070 g cm−3. Solubility: miscible organic alcohols, esters, ethers. R = Et: insol H2O. R = Me: sol 13.9 g per 100 g H2O at 20 °C. Form Supplied in: readily available; inexpensive. Preparative Methods: traditionally prepared by reacting MeOH with phosgene. Contemporary industrial synthesis by oxycarbonylation of CO with MeOH/O2 (Enichem) or MeOH/NO/O2 (UBE).1d Purification: can be purchased without need for further purification. May be distilled from calcium hydride.1e Handling, Storage, and Precautions: dimethyl carbonate (DMC) is highly flammable and should be stored appropriately. DMC may cause eye, skin, and respiratory tract irritation. Consequently, proper protective equipment should be used and operations involving this reagent should be conducted within a well-ventilated fume hood.