Dimethyl malonate

Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.[2]

Dimethyl malonate[1]
Skeletal formula of dimethyl malonate
Ball-and-stick model of the dimethyl malonate molecule
Names
Preferred IUPAC name
Dimethyl propanedioate
Other names
Malonic acid dimethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.271
UNII
  • InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 checkY
    Key: BEPAFCGSDWSTEL-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3
    Key: BEPAFCGSDWSTEL-UHFFFAOYAJ
  • COC(=O)CC(=O)OC
Properties
C5H8O4
Molar mass 132.115 g·mol−1
Appearance Colorless liquid
Density 1.154
Melting point −62 °C (−80 °F; 211 K)
Boiling point 180 to 181 °C (356 to 358 °F; 453 to 454 K)
Slightly soluble
-69.69·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethyl malonate is used extensively in the fragrance industry as a raw material in the synthesis of jasmonates. For example, methyl dihydrojasmonate is synthesized from cyclopentanone, pentanal and dimethyl malonate.[3] Hedione is used in almost all fine fragrances and is found in Christian Dior's Eau Sauvage and "Diorella", Hermes' "Voyage d'Hermes Parfum", Calvin Klein's "CKOne", Chanel's "Chanel No. 19", and Mark Jacob's "Blush", among others. As of 2009, Hedione was Firmenich's top selling compound by volume.[4]

Hebei Chengxin is the world's largest producer of dimethyl malonate by volume and uses a chloroacetic acid/sodium cyanide process developed in the 1940s.[5]

See also

References
  1. Merck Index, 11th Edition, 6009.
  2. R. A. Sheldon (1983), Chemicals from Synthesis Gas: Catalytic Reactions of CO and (in German), Springer, p. 207, ISBN 902771489-4
  3. Schaefer, Bernd (2014). Natural Products in the Chemical Industry. Springer. p. 91–92. ISBN 978-3-642-54461-3.
  4. Davies, E. (2009). "The sweet scent of success" (PDF). Chemistry World: 40–44.
  5. Stoesser, WC. "Preparation of malonic esters," US Patent 2337858
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