Dimethyl malonate

Dimethyl malonate[1]
Names
	IUPAC name Propanedioic acid dimethyl ester
	Other names Malonic acid dimethyl ester
Identifiers
CAS Number	108-59-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106102 ;
ECHA InfoCard	100.003.271
PubChem CID	7943;
UNII	EM8Y79998C ;
CompTox Dashboard (EPA)	DTXSID4029145 ;
	InChI InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 Key: BEPAFCGSDWSTEL-UHFFFAOYSA-N ; InChI=1/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 Key: BEPAFCGSDWSTEL-UHFFFAOYAJ;
	SMILES COC(=O)CC(=O)OC;
Properties
Chemical formula	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)
Solubility in water	Slightly soluble
Magnetic susceptibility (χ)	-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 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]

\mathrm {H_{2}C(OCH_{3})_{2}+2\ CO\longrightarrow CH_{2}(CO_{2}CH_{3})_{2}}

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]

References

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

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[1] Merck Index, 11th Edition, 6009.

[R._A._Sheldon-2] R. A. Sheldon (1983), [, p. 207, at Google Books Chemicals from Synthesis Gas: Catalytic Reactions of CO and] Check |url= value (help) (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

Dimethyl malonate

See also

References