| Identification | More | [Name]
Diethyl malonate | [CAS]
105-53-3 | [Synonyms]
AKOS BBS-00004262
CARBETHOXYACETIC ESTER
DEM
DICARBETHOXYMETHANE
DIETHYL MALONATE
DIETHYL PROPANEDIOATE
ETHYL MALONATE
Ethyl propanedioate
FEMA 2375
MALONIC ACID DIETHYL ESTER
MALONIC ESTER
METHYLMALONIC ACID DIETHYL ESTER
methyl-propanedioic acid diethyl ester
Diethyl1,3-propanedioate
Methanedicarboxylic acid, diethyl ester
methanedicarboxylicacid,diethylester
Propanedioicacid,diethylester
Propanedioicaciddiethylester
Diethyl malonat
Malonic Acid Diethyl Ester (DEM) | [EINECS(EC#)]
203-305-9 | [Molecular Formula]
C7H12O4 | [MDL Number]
MFCD00009195 | [Molecular Weight]
160.17 | [MOL File]
105-53-3.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [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)
| [FEMA ]
2375 | [refractive index ]
n20/D 1.413(lit.)
| [Fp ]
212 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
20.8g/l (External MSDS) | [form ]
Liquid | [pka]
13.5(at 25℃) | [color ]
colourless liquid | [Odor]
Sweet ester odor | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, | [explosive limit]
0.8-12.8%(V) | [Odor Type]
fruity | [Water Solubility ]
Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water. | [JECFA Number]
614 | [Merck ]
14,3823 | [BRN ]
774687 | [Dielectric constant]
7.9（21℃） | [InChIKey]
IYXGSMUGOJNHAZ-UHFFFAOYSA-N | [LogP]
0.96 at 20℃ | [CAS DataBase Reference]
105-53-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Propanedioic acid, diethyl ester(105-53-3) | [EPA Substance Registry System]
105-53-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
OO0700000
| [Autoignition Temperature]
435 °C DIN 51794 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29171910 | [Safety Profile]
Mildly 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. | [Hazardous Substances Data]
105-53-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethanol-->Hydrochloric acid-->Sulfuric acid-->Sodium carbonate-->Sodium cyanide-->Malonic acid-->Chloroacetic acid-->Sodium chloroacetate-->Cyanoacetic acid-->Sodium Phosphate, Dibasic-->MALONIC ACID DISODIUM SALT | [Preparation Products]
2-Hexyldecanoic Acid-->CYCLOPENTYLACETIC ACID-->5-CHLORO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER-->Enoxacin-->Phenylbutazone-->4,6-Dichloro-2-(methylsulfonyl)pyrimidine-->2-Benzofurancarboxylic acid ethyl ester-->5-NITROBENZOFURAN-2-CARBOXYLIC ACID-->4-CHLORO-2-METHANESULFONYL-6-METHOXY-PYRIMIDINE-->Diethyl chloromalonate-->ETHYL 7-METHOXYBENZOFURAN-2-CARBOXYLATE-->5,7-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE-->2-Mercapto-4,6-dimethoxypyrimidine-->4-Chloro-6-methoxy-2-(methylthio)pyrimidine-->5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-->2-(TRIFLUOROMETHYL)-4-HYDROXYPYRIMIDINE-5-CARBOXYLIC ACID-->5-Nitropyridine-2-carboxylic acid-->2-ETHOXY-MALONIC ACID DIETHYL ESTER-->2,4-Dihydroxypyrimidine-5-carboxylic acid-->4,6-Dihydroxy-2-methylpyrimidine-->5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID-->4-Chloro-7-(trifluoromethyl)quinoline-->ETHYL 4-CHLORO-6-(TRIFLUOROMETHYL)-3-QUINOLINECARBOXYLATE-->4-HYDROXY-5,7-BIS-TRIFLUOROMETHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER-->Triethyl 1,1,2-ethanetricarboxylate-->ETHYL 2-(ETHYLTHIO)-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE-->2,4,5-Trifluorophenylacetic acid-->Gliclazide-->2-MERCAPTOPYRIMIDINE-4,6-DIOL-->ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE-->Diethyl butylmalonate-->2-AMINODIETHYLMALONATE-->2-amino-6-chloropyrimidin-4(3H)-one-->3-CARBETHOXYUMBELIFERONE-->DIETHYL 2-(2-CYANOETHYL)MALONATE-->5-CARBETHOXYURACIL-->3-CARBETHOXY-2-PIPERIDONE-->2-Amino-6-hydroxypyrimidin-4(3H)-one ,97%-->Sulfamonomethoxine |
| Questions And Answer | Back Directory | [Description]
As 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.
| [uses]
Diethyl malonate is the diethyl ester of malonic acid. It naturally occuring in grapes and strawberries, is widely used in the manufacture of pharmaceuticals, antioxidants, and dyes.
Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate. | [References]
https://en.wikipedia.org/wiki/Diethyl_malonate
https://pubchem.ncbi.nlm.nih.gov/compound/7761#section=Safety-and-Hazards
https://www.alfa.com/zh-cn/catalog/A15468/
http://www.hmdb.ca/metabolites/HMDB29573
http://www.chemicalland21.com/industrialchem/organic/DIETHYL%20MALONATE.htm
|
| Hazard Information | Back Directory | [Chemical Properties]
colourless liquid | [Chemical Properties]
Diethyl malonate has a faint, pleasant, aromatic odor.
| [Occurrence]
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy,
port, cider, sherry and red, white, strawberry and bilberry wines. | [Uses]
Diethyl 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. | [Uses]
manufacture of barbiturates. | [Definition]
ChEBI: Ethyl malonate is a dicarboxylic acid. | [Preparation]
Reacting 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 values]
Taste 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 | [General Description]
Diethyl malonate is diethyl ester of malonic acid. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones. | [Metabolism]
When 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 Methods]
If 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.] |
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