Diethyl ketomalonate

Synonym(s):Diethyl mesoxalate;Ketomalonic acid diethyl ester

CAS NO.：609-09-6
Empirical Formula: C7H10O5
Molecular Weight: 174.15
MDL number: MFCD00009121
EINECS: 210-176-2
SAFETY DATA SHEET (SDS)
Update Date: 2024-05-21 17:03:17

What is Diethyl ketomalonate?

Chemical properties

Clear yellow liquid

The Uses of Diethyl ketomalonate

Diethyl ketomalonate, reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles, and 2-azadienes, respectively.

Synthesis Reference(s)

Synthetic Communications, 24, p. 695, 1994 DOI: 10.1080/00397919408012648
The Journal of Organic Chemistry, 46, p. 2598, 1981 DOI: 10.1021/jo00325a039

Chemical properties

Diethyl ketomalonate 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. 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.

Properties of Diethyl ketomalonate

Melting point:	-70°C
Boiling point:	208-210 °C (lit.)
Density	1.142 g/mL at 25 °C (lit.)
refractive index	n20/D 1.415
Flash point:	>230 °F
storage temp.	Inert atmosphere,Room Temperature
solubility	Chloroform (Slightly), Methanol
form	liquid
color	green-yellow
Specific Gravity	1.142
Water Solubility	Fully miscible with water.
Sensitive	Moisture Sensitive
Merck	14,5913
BRN	971873
CAS DataBase Reference	609-09-6(CAS DataBase Reference)
NIST Chemistry Reference	Propanedioic acid, oxo-, diethyl ester(609-09-6)
EPA Substance Registry System	Propanedioic acid, oxo-, diethyl ester (609-09-6)

Safety information for Diethyl ketomalonate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection.