Dimethyl carbonate

Dimethyl carbonate, often abbreviated DMC, is a flammable clear liquid boiling at 90 °C, insoluble in water. It has recently found use as a methylating reagent. Its main benefit over other methylating reagents such as iodomethane and dimethyl sulfate is its lesser toxicity and its biodegradability.^[1] Also, it is now prepared from catalytic oxidative carbonylation of methanol with oxygen, instead of from phosgene making its production non-toxic and environmentally friendly.^[1] This allows dimethyl carbonate to be considered a green reagent.

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Dimethyl carbonate is able to methylate anilines, phenols and carboxylic acids, but many of these reactions require the use of an autoclave.^[2] One alternative involves the use of DBU, which allows methylation of carboxylic acids to occur in refluxing DMC.^[2]

References

1. ^ ^{a b} Pietro Tundo and Maurizio Selva (2002). "The Chemistry of Dimethyl Carbonate". Acc. Chem. Res. 35 (9): 706-16. doi:10.1021/ar010076f.
2. ^ ^{a b} Shieh, Wen-Chung; Dell, Stephen; Repič, Oljan (2002). "Nucleophilic Catalysis with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) for the Esterification of Carboxylic Acids with Dimethyl Carbonate". J. Org. Chem. 67 (7): 2188-2191. doi:10.1021/jo011036s.