Dimethyl malonate

Synonym(s):Dimethyl malonate;Malonic acid dimethyl ester

CAS NO.：108-59-8
Empirical Formula: C5H8O4
Molecular Weight: 132.11
MDL number: MFCD00008460
EINECS: 203-597-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-05-15 13:17:26

What is Dimethyl malonate?

Description

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.

Chemical properties

liquid

Chemical properties

Dimethyl malonate is soluble in alcohol and ether and very slightly soluble in water. It may slowly decompose.

The Uses of Dimethyl malonate

Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.

The Uses of Dimethyl malonate

It is used in fragrances and some artificial flavorings .

What are the applications of Application

Dimethyl malonate is a diester derivative of Malonic Acid

Production Methods

Dimethyl malonate is produced via direct esterification of methanol with malonic acid under azeotropic conditions.

What are the applications of Application

Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.
Dimethyl malonate was used in gold catalyzed oxidative esterification of glycerol, 1,2-propanediol and 1,3-propanediol.

General Description

Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.

Properties of Dimethyl malonate

Melting point:	-62 °C (lit.)
Boiling point:	180-181 °C (lit.)
Density	1.156 g/mL at 25 °C (lit.)
vapor density	>1 (vs air)
vapor pressure	0.15 hPa (20 °C)
refractive index	n20/D 1.413(lit.)
Flash point:	194 °F
storage temp.	Store below +30°C.
solubility	alcohol: miscible
form	Liquid
pka	11.80±0.46(Predicted)
color	Clear colorless
Odor	fruity
explosive limit	1.3-17.4%(V)
Water Solubility	negligible
Merck	14,6096
BRN	774261
Dielectric constant	10.4（20℃）
Stability:	Stable. Incompatible with strong oxidizing agents. Flammable.
CAS DataBase Reference	108-59-8(CAS DataBase Reference)
NIST Chemistry Reference	Propanedioic acid, dimethyl ester(108-59-8)
EPA Substance Registry System	Dimethyl malonate (108-59-8)

Safety information for Dimethyl malonate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention.