|IUPAC name||Dimethyl carbonate|
Carbonic acid, dimethyl ester
3D model (JSmol)
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|Molar mass||90.08 g/mol|
|Density||1.069 - 1.073 g/ml, liquid|
|Except where noted otherwise, data are given for|
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
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. 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. This allows dimethyl carbonate to be considered a green reagent.
Dimethyl carbonate is able to methylate anilines, phenols and carboxylic acids, but many of these reactions require the use of an autoclave. One alternative involves the use of DBU, which allows methylation of carboxylic acids to occur in refluxing DMC.
- Pietro Tundo and Maurizio Selva (2002). "The Chemistry of Dimethyl Carbonate". Acc. Chem. Res. 35 (9): 706–16. doi:10.1021/ar010076f.
- Shieh, Wen-Chung (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. Unknown parameter