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Dimethyl malonate

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Dimethyl malonate Basic information

Product Name:
Dimethyl malonate
Synonyms:
  • dimthyl malonate
  • DiMethyl Malonate, 97% 250ML
  • Malonic Acid Dimethyl Ester Methyl Malonate
  • DIMETHYL MALONATE FOR SYNTHESIS
  • Propanedioicacid, 1,3-diMethyl ester
  • Malonic acid d
  • Dimethyl malonate Vetec(TM) reagent grade, 98%
  • PROPANEDIOIC ACID DIMETHYL ESTER
CAS:
108-59-8
MF:
C5H8O4
MW:
132.11
EINECS:
203-597-8
Product Categories:
  • Thiazoles
  • Building Blocks
  • C2 to C5
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • C2 to C5
  • Carbonyl Compounds
  • Esters
  • bc0001
  • 108-59-8
Mol File:
108-59-8.mol
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Dimethyl malonate Chemical Properties

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)
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Safety Information

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

MSDS

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Dimethyl malonate Usage And Synthesis

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.

Dimethyl malonateSupplier

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