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Dimethyl malonate

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CAS:108-59-8
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Dimethyl malonate Basic information
Product Name:Dimethyl malonate
Synonyms: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;Dimethyl malonate, 98+%
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
Dimethyl malonate Structure
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.)
Fp 194 °F
storage temp. Store below +30°C.
solubility alcohol: miscible
form Liquid
pka11.80±0.46(Predicted)
color Clear colorless
Odorfruity
explosive limit1.3-17.4%(V)
Water Solubility negligible
Merck 14,6096
BRN 774261
Dielectric constant10.4(20℃)
Stability:Stable. Incompatible with strong oxidizing agents. Flammable.
InChIKeyBEPAFCGSDWSTEL-UHFFFAOYSA-N
LogP-0.05 at 20-25℃ and pH6.4
CAS DataBase Reference108-59-8(CAS DataBase Reference)
NIST Chemistry ReferencePropanedioic acid, dimethyl ester(108-59-8)
EPA Substance Registry SystemDimethyl malonate (108-59-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 1
RTECS OO0950000
Autoignition Temperature440 °C
Hazard Note Irritant
TSCA Yes
HS Code 29171910
ToxicityLD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg
MSDS Information
ProviderLanguage
Methyl malonate English
SigmaAldrich English
ACROS English
ALFA English
Dimethyl malonate Usage And Synthesis
DescriptionDimethyl 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 Propertiesliquid
Chemical PropertiesDimethyl malonate is soluble in alcohol and ether and very slightly soluble in water. It may slowly decompose.
UsesIt is used in fragrances and some artificial flavorings .
UsesDimethyl 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.
ApplicationDimethyl 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 MethodsDimethyl malonate is produced via direct esterification of methanol with malonic acid under azeotropic conditions.
General DescriptionDimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.
Tag:Dimethyl malonate(108-59-8) Related Product Information
Methyl acetate Dacthal N,N-Dimethylformamide Dimethyl carbonate Tribenuron methyl Thiophanate-methyl Dimethyl disulfide Dimethyl phthalate Methyl salicylate Dimethyl ether Diethyl methylmalonate Dimethyl fumarate 2-Methylpropanedioic acid Dimethyl sulfoxide ETHANE Kresoxim-methyl METSULFURON METHYL Malonic acid