Dimethyl malonate Property

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

pka

11.80±0.46(Predicted)

form 

Liquid

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.

InChIKey

BEPAFCGSDWSTEL-UHFFFAOYSA-N

LogP

-0.05 at 20-25℃ and pH6.4

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

OO0950000

Autoignition Temperature

440 °C

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29171910

Toxicity

LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

Dimethyl malonate Chemical Properties,Usage,Production

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.

Uses

It is used in fragrances and some artificial flavorings .

Uses

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.

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.

Production Methods

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

General Description

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