ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Carboxylic acids and esters > Aliphatic dicarboxylic acid esters > Diethyl malonate
Diethyl malonate Chemical Properties
- Melting point:-51--50 °C (lit.)
- Boiling point:199 °C (lit.)
- Density 1.055 g/mL at 25 °C (lit.)
- vapor density 5.52 (vs air)
- vapor pressure 1 mm Hg ( 40 °C)
- refractive index n
- FEMA 2375 | DIETHYL MALONATE
- Flash point:212 °F
- storage temp. Store below +30°C.
- solubility 20.8g/l (External MSDS)
- pka13.5(at 25℃)
- form Liquid
- explosive limit0.8-12.8%(V)
- Water Solubility Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
- JECFA Number614
- Merck 14,3823
- BRN 774687
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents,
- CAS DataBase Reference105-53-3(CAS DataBase Reference)
- NIST Chemistry ReferencePropanedioic acid, diethyl ester(105-53-3)
- EPA Substance Registry SystemDiethyl malonate (105-53-3)
- Hazard Codes Xi
- Risk Statements 36/37/38-36
- Safety Statements 24/25-26
- WGK Germany 1
- RTECS OO0700000
- Autoignition Temperature435 °C DIN 51794
- Hazard Note Irritant
- TSCA Yes
- HS Code 29171910
- Hazardous Substances Data105-53-3(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg
Diethyl malonate Usage And Synthesis
- DescriptionAs an organic compound, diethyl malonate belongs to the diethyl ester of malonic acid, which is present naturally in guava fruits, melons, grapes, pineapples, blackberries and strawberries as a colorless liquid with an apple-like odor. It is a flavor ingredient commonly found in perfumes, artificial flavorings, alcoholic beverages, various wines and spirits due to its natural pleasant odor. It is also used as an essential intermediate in the syntheses of numerous pharmaceuticals, such as barbiturates, vitamins B1 and B6, non-steroidal anti-inflammatory agents. Besides, diethyl malonate is also involved in organic synthesis of other compounds, such as alpha-aryl malonates, mono-substituted and di-substituted acetic acid. And it can react with benzaldehyde for the production of diethyl benzylidenemalonate in Knoevenagel condensation reaction.
- Chemical Propertiescolourless liquid
- Chemical PropertiesDiethyl malonate has a faint, pleasant, aromatic odor.
- OccurrenceReported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy, port, cider, sherry and red, white, strawberry and bilberry wines.
- UsesDiethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.
- Usesmanufacture of barbiturates.
- PreparationReacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is finally esterified by azeotropic distillation with ethanol in benzene
- Taste threshold valuesTaste characteristics at 50 ppm: sweet and fruity with apple and pineapple nuances.
- Synthesis Reference(s)The Journal of Organic Chemistry, 46, p. 3151, 1981 DOI: 10.1021/jo00328a041
Tetrahedron Letters, 36, p. 3997, 1995 DOI: 10.1016/0040-4039(95)00697-B
- Safety ProfileMildly toxic by ingestion. A skin irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water to blanket fire, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
- MetabolismWhen the ester was fed to chicks at a level of 5% in the diet, 32% of the energy from diethyl malonate was available (Yoshida et al. 1970). Hydrolysis of diethyl malonate would produce ethanol and malonic acid, which is a relatively strong acid and acts as an inhibitor of enzymes, including succinic dehydrogenase (Fassett, 1963). Malonic acid injected into rats or rabbits is excreted largely unchanged, but also causes increased excretion of citric and a-ketoglutaric acids (Krebs, Salvin & Johnson, 1938). Some malonate may be metabolized through the tricarboxylic acid cycle, with decarboxylation to acetate followed by transformation to succinate, which has been detected in rat urine (Lee & Lifson, 1951). Diethyl malonate was hydrolysed by adipose-tissue lipase (Lynn & Perryman, 1960) and to the monoester by α-chymotrypsin (Cohen & Crossely, 1964). It was oxidized in 110 min to the extent of 34% by the homogenized mycelium of urethane-grown Streptomyces nitrifica (Schatz, Trelawny, Schatz & Mohan, 1957).
- Purification MethodsIf too impure (IR, NMR) the ester (250g) is heated on a steam bath for 36hours with absolute EtOH (125mL) and conc H2SO4 (75mL), then fractionally distilled under reduced pressure. Otherwise fractionally distil it under reduced pressure and collect the steady boiling middle fraction. [Beilstein 2 IV 1881.]
Diethyl malonate Preparation Products And Raw materials
- Preparation Products2-HEXYLDECANOIC ACIDCYCLOPENTYLACETIC ACID5-CHLORO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTEREnoxacinPhenylbutazone4,6-Dichloro-2-(methylsulfonyl)pyrimidine2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER5-NITROBENZOFURAN-2-CARBOXYLIC ACID4-CHLORO-2-METHANESULFONYL-6-METHOXY-PYRIMIDINEDiethyl chloromalonateETHYL 7-METHOXYBENZOFURAN-2-CARBOXYLATE5,7-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE2-Mercapto-4,6-dimethoxypyrimidine4-Chloro-6-methoxy-2-(methylthio)pyrimidine ,98%5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE2-(TRIFLUOROMETHYL)-4-HYDROXYPYRIMIDINE-5-CARBOXYLIC ACID5-Nitropyridine-2-carboxylic acid2-ETHOXY-MALONIC ACID DIETHYL ESTER2,4-Dihydroxypyrimidine-5-carboxylic acid4,6-Dihydroxy-2-methylpyrimidine5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID4-Chloro-7-(trifluoromethyl)quinolineETHYL 4-CHLORO-6-(TRIFLUOROMETHYL)-3-QUINOLINECARBOXYLATE4-HYDROXY-5,7-BIS-TRIFLUOROMETHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTERTRIETHYL 1,1,2-ETHANETRICARBOXYLATEETHYL 2-(ETHYLTHIO)-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE2,4,5-Trifluorophenylacetic acidGliclazide2-MERCAPTOPYRIMIDINE-4,6-DIOLETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATEDiethyl butylmalonate2-AMINODIETHYLMALONATE2-amino-6-chloropyrimidin-4(3H)-one3-CARBETHOXYUMBELIFERONEDIETHYL 2-(2-CYANOETHYL)MALONATE5-CARBETHOXYURACIL3-CARBETHOXY-2-PIPERIDONE2-Amino-6-hydroxypyrimidin-4(3H)-one ,97%Sulfamonomethoxine
- Raw materialsEtanolHydrochloric acidSulfuric acid Sodium carbonateSodium cyanideMalonic acidChloroacetic acidChloroacetic acid sodium saltCyanoacetic acidDisodium hydrogenorthophosphateMALONIC ACID DISODIUM SALT
- Diisopropyl malonate TERT-BUTYL ETHYL MALONATE 2-Hexenamide, 2-cyano-5-methyl- Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)- 2,4-Dicyano-3-(2-Methylpropyl)-pentanediaMide 3-((methoxycarbonyl)methyl)-5-methylhexanoic acid 4,9-diisobutyl-1,6-diazecane-2,7-dione Pregabalin Impurity PD0224377 Pregabalin Impurity 49 4-Isobutyl-2-pyrrolidinone PD 312236 Pregabalin Impurity 28 Pregabalin Impurity D: Pregabalin-2-ene Hexanoic acid, 3-cyano-5-methyl-, (3R)- (S)-Pregabalin Methyl Ester 2-ISOBUTYL SUCCINIC ACID (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Pregabalin Impurity 4
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