My watch list  

Dimethyl carbonate

Dimethyl carbonate
IUPAC name Dimethyl carbonate
Other names DMC
Methyl carbonate
Carbonic acid, dimethyl ester
CAS number 616-38-6
Molecular formula C3H6O3
Molar mass 90.08 g/mol
Appearance Clear liquid
Density 1.069 - 1.073 g/ml, liquid
Melting point

2 - 4 °C (275 - 277 K)

Boiling point

90 °C (363 K)

Solubility in water Insoluble
Main hazards Flammable
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.[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.

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]


  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.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dimethyl_carbonate". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE