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Dimethyl carbonate
Dimethyl carbonate
Ball-and-stick model of dimethyl carbonate
IUPAC name
Other names DMC
Methyl carbonate
Carbonic acid, dimethyl ester
Identifiers
CAS number 616-38-6 Yes check.svgY
SMILES
Properties
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 13.9 g/100 ml water
Hazards
Main hazards Flammable
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimethyl carbonate, often abbreviated DMC, is a flammable clear liquid boiling at 90 °C. It is a carbonate ester which 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 carbon monoxide and 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]

Methylation of phenylacetic acid by dimethyl carbonate promoted by DBU

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.  
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