| Dimethyl carbonate | |
|---|---|
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| IUPAC name | Dimethyl carbonate |
| Other names | DMC Methyl carbonate Carbonic acid, dimethyl ester |
| Identifiers | |
| CAS number | |
| SMILES | COC(=O)OC |
| 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 | Insoluble |
| 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 |
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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]
References
- ^ a b Pietro Tundo and Maurizio Selva (2002). "The Chemistry of Dimethyl Carbonate". Acc. Chem. Res. 35 (9): 706-16. doi:10.1021/ar010076f.
- ^ 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.
