Dimethyl malonate

Dimethyl malonate[1]
Skeletal formula of dimethyl malonate
Ball-and-stick model of the dimethyl malonate molecule
Names
IUPAC name
propanedioic acid dimethyl ester
Other names
Malonic acid dimethyl ester
Identifiers
108-59-8 YesY
3D model (Jmol) Interactive image
ChemSpider 21106102 YesY
ECHA InfoCard 100.003.271
PubChem 7943
Properties
C5H8O4
Molar mass 132.115
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
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 a diester derivative of malonic acid. It is a common reagent for organic synthesis, e.g. as a precursor for barbituric acid. It is used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.

Dimethyl malonate is used extensively in the fragrance industry as a raw material in the synthesis of jasmonates. For example, methyl dihydrojasmonate, sold under the tradename Hedione by Firmenich, is synthesized from cyclopentanone, pentanal, and dimethyl malonate.[2] 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.[3]

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.[4] The 2015 Tianjin explosions in China were due, in part, to storage of cyanide produced by Hebei Chengxin in a port warehouse.[5] Both cyanide and chloroacetic acid are included on the List of extremely hazardous substances defined by the U.S. federal government. GoodGuide evaluated chloroacetic acid as one of the most hazardous chemicals (worst 10%) to ecosystems and human health.[6]

See also

References

  1. ↑ Merck Index, 11th Edition, 6009.
  2. ↑ Schaefer, Bernd. "Natural Products in the Chemical Industry" Springer, pgs 91-92 (2014). ISBN 978-3-642-54461-3
  3. ↑ Davies, E. ″The sweet scent of success,″ Chemistry World, pg 40-44 (2009).
  4. ↑ Stoesser, WC. "Preparation of malonic esters," US Patent 2337858
  5. ↑ Zuo, M., Le Huang, K. "Public anger grows as China confirms hundreds of tonnes of cyanide were held at blast-hit port of Tianjin," South China Morning Post, (2016-08-17)
  6. ↑ http://scorecard.goodguide.com/chemical-profiles/summary.tcl?edf_substance_id=79-11-8


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