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Dimethyl carbonate is used as a solvent in organic synthesis and considered as a replacement for solvent like methyl ethyl ketone, tert-butyl acetate and parachlorobenzotrifluoride. It is involved as an intermediate in the preparation of diphenylcarbonate, which in turn is used as a key raw material for the synthesis of Bisphenol-A-polycarbonate. It is also used as a 'green' methylating agent involved in the methylation of aniline, phenols and carboxylic acids. It can be used as a fuel additive due to its high oxygen content. It also finds applications related to supercapacitors and lithium batteries.
Conversion of a ketone to its methoxycarbonyl derivative has been used to change the preferred site of chlorination to the less-substituted carbon atom: Synthesis, 188 (1987):
Grignard reagents react in THF to give methyl esters, providing a high-yield, one-pot synthesis of carboxylic esters from alkyl or aryl halides: Synth. Commun., 20, 3273 (1990).
Useful alkylating agent. Although less reactive, dimethyl carbonate has the advantage of much lower toxicity than the more usual sulfate or iodide. In the presence of K2CO3 and 18-crown-6, alcohols, phenols, thiols, imidazoles, etc. can be methylated: Synthesis, 382 (1986). For K2CO3 promoted alkylation of active methylene compounds at 180-220o (pressure), see: Rec. Trav. Chim., 115, 256 (1996); Org. Synth., 76, 169 (1998). Other dialkyl carbonates behave similarly.
For other reactions of dialkyl carbonates, see Diethyl carbonate, A12477.
Nale, D. B.; Bhanage, B. M. Copper-catalyzed efficient synthesis of a 2-benzimidazolone scaffold from 2-nitroaniline and dimethyl carbonate via a hydrosilylation reaction. Green Chem. 2015, 17 (4), 2480-2486.
Earle, M. J.; Noe, M.; Perosa, A.; Seddon, K. R. Improved synthesis of tadalafil using dimethyl carbonate and ionic liquids. RSC Adv. 2014, 4 (3), 1204-1211.
Mentions de danger (UE): H225
Highly flammable liquid and vapour.
Mentions de prudence: P210-P280a-P240-P241-P303+P361+P353-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.