Dimethyl malonate

{{chembox

| Watchedfields = changed

| verifiedrevid = 421096900

| Reference =Merck Index, 11th Edition, 6009.

| ImageFile =dimethyl malonate.png

| ImageSize =180px

| ImageAlt = Skeletal formula of dimethyl malonate

| ImageFile1 = Dimethyl malonate 3D ball.png

| ImageAlt1 = Ball-and-stick model of the dimethyl malonate molecule

| PIN = Dimethyl propanedioate

| OtherNames = Malonic acid dimethyl ester

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21106102

| InChI = 1/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3

| InChIKey = BEPAFCGSDWSTEL-UHFFFAOYAJ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BEPAFCGSDWSTEL-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =108-59-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EM8Y79998C

| PubChem =7943

| SMILES =COC(=O)CC(=O)OC

}}

|Section2={{Chembox Properties

| C=5|H=8|O=4

| Appearance =Colorless liquid

| Density =1.154

| MeltingPtC =-62

| BoilingPtC = 180 to 181

| BoilingPt_notes =

| Solubility =Slightly soluble

| MagSus = −69.69·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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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.{{citation|surname1=R. A. Sheldon|title=Chemicals from Synthesis Gas: Catalytic Reactions of CO and|publisher=Springer|page=207|isbn=902771489-4|date=1983|language=German|url={{Google books|s1_rjRUlu1EC||page=207|plainurl=yes}}}}

::$\backslash mathrm\{H\_2C(OCH\_3)\_2\; +\; 2\; \backslash \; CO\; \backslash longrightarrow\; CH\_2(CO\_2CH\_3)\_2\}$

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.{{Cite book|author=Schaefer, Bernd|url=https://www.springer.com/us/book/9783642544606|title=Natural Products in the Chemical Industry|publisher=Springer|pages=91–92|date=2014|isbn=978-3-642-54461-3}} 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.{{cite journal|author = Davies, E.|url=http://www.rsc.org/images/Fragrance_tcm18-142947.pdf|title=The sweet scent of success|journal=Chemistry World|pages=40–44|date=2009}}

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.Stoesser, WC. "Preparation of malonic esters," [https://patents.google.com/patent/US2337858 US Patent 2337858]