Dimethyl carbonate

Jump to: navigation, search
Template:Chembox E numberTemplate:Chembox SolubilityInWater
Dimethyl carbonate
IUPAC name Dimethyl carbonate
Other names DMC
Methyl carbonate
Carbonic acid, dimethyl ester
Identifiers
3D model (JSmol)
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
Properties
C3H6O3
Molar mass 90.08 g/mol
Appearance Clear liquid
Density 1.069 - 1.073 g/ml, liquid
Melting point
Boiling point
Hazards
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]

Methylation of phenylacetic acid by dimethyl carbonate promoted by DBU

References

  1. 1.0 1.1 Pietro Tundo and Maurizio Selva (2002). "The Chemistry of Dimethyl Carbonate". Acc. Chem. Res. 35 (9): 706–16. doi:10.1021/ar010076f.
  2. 2.0 2.1 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 |coauthors= ignored (help)

de:Dimethylcarbonat fi:Dimetyylikarbonaatti


Linked-in.jpg