Diethyl oxomalonate information

Diethyl oxomalonate
Names
	Preferred IUPAC name Diethyl oxopropanedioate
	Other names Diethyl mesoxalate; Ethyl ketomalonate; Diethyl ketomalonate
Identifiers
CAS Number	609-09-6 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.009.252
PubChem CID	69105;
UNII	H28C8N13IK ;
CompTox Dashboard (EPA)	DTXSID5060566 ;
	InChI InChI=1S/C7H10O5/c1-3-11-6(9)5(8)7(10)12-4-2/h3-4H2,1-2H3 Key: DBKKFIIYQGGHJO-UHFFFAOYSA-N;
	SMILES CCOC(=O)C(=O)C(=O)OCC;
Properties
Chemical formula	C7H10O5
Molar mass	174.152 g·mol−1
Appearance	Clear colorless to yellow liquid
Density	1.142 g/cm3
Melting point	−30 °C (−22 °F; 243 K)
Boiling point	208–210 °C (406–410 °F; 481–483 K) ; 96–97 °C (12 mmHg)
Solubility in water	Highly soluble
Solubility in ethanol, diethylether, chloroform	Soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH₂)_n–COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine). Diethyl oxomalonate reacts because of its highly polarized keto group as electrophile in addition reactions and is a highly active reactant in pericyclic reactions such as the Diels-Alder reactions, cycloadditions or ene reactions.^[1] At humid air, mesoxalic acid diethyl ester reacts with water to give diethyl mesoxalate hydrate and the green-yellow oil are spontaneously converted to white crystals.^[5]

^ ^a ^b T.F. Tietze; C. Schneider; D.J. Coughlin (2009), "Diethyl Oxomalonate", e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rd207m.pub2
^ ^a ^b ^c Sigma-Aldrich Co., product no. {{{id}}}.
^ "Diethyl ketomalonate". Alfa Aesar. Retrieved 15 November 2017.
^ W.M. Haynes (2015), CRC Handbook of Chemistry and Physics, 96th Edition, Boca Raton, Fla., U.S.A.: CRC Press, pp. 3–178, ISBN 978-1-4822-6097-7
^ R. Müller (1933), "Zur Kenntnis der spezifischen Oxydationswirkung des Selendioxyds", Chemische Berichte (in German), vol. 66, no. 11, pp. 1668–1670, doi:10.1002/cber.19330661111

[Tietze-1] T.F. Tietze; C. Schneider; D.J. Coughlin (2009), "Diethyl Oxomalonate", e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rd207m.pub2

[Sigma-2] Sigma-Aldrich Co., product no. {{{id}}}.

[Alfa-3] "Diethyl ketomalonate". Alfa Aesar. Retrieved 15 November 2017.

[CRC-4] W.M. Haynes (2015), CRC Handbook of Chemistry and Physics, 96th Edition, Boca Raton, Fla., U.S.A.: CRC Press, pp. 3–178, ISBN 978-1-4822-6097-7

[Müller-5] R. Müller (1933), "Zur Kenntnis der spezifischen Oxydationswirkung des Selendioxyds", Chemische Berichte (in German), vol. 66, no. 11, pp. 1668–1670, doi:10.1002/cber.19330661111

Diethyl oxomalonate information

and 3 Related for: Diethyl oxomalonate information

Diethyl oxomalonate

C7H10O5

Mesoxalic acid