Description References
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Product Name: |
Diethyl malonate |
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Synonyms: |
MALONIC ACID DIETHYL ESTER;MALONIC ESTER;ETHYL MALONATE;Ethyl propanedioate;FEMA 2375;DEM;DICARBETHOXYMETHANE;DIETHYL MALONATE |
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CAS: |
105-53-3 |
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MF: |
C7H12O4 |
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MW: |
160.17 |
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EINECS: |
203-305-9 |
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Product Categories: |
Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organics;Organic Building Blocks |
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Mol File: |
105-53-3.mol |
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Melting point |
-50 °C |
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Boiling point |
199 °C(lit.) |
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density |
1.055 g/mL at 25 °C(lit.) |
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vapor density |
5.52 (vs air) |
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vapor pressure |
1 mm Hg ( 40 °C) |
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FEMA |
2375 | DIETHYL MALONATE |
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refractive index |
n20/D 1.413(lit.) |
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Fp |
212 °F |
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storage temp. |
Store below +30°C. |
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solubility |
20.8g/l (External MSDS) |
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pka |
13.5(at 25℃) |
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form |
Liquid |
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explosive limit |
0.8-12.8%(V) |
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Water Solubility |
Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water. |
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JECFA Number |
614 |
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Merck |
14,3823 |
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BRN |
774687 |
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Stability: |
Stable. Combustible. Incompatible with strong oxidizing agents, |
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InChIKey |
IYXGSMUGOJNHAZ-UHFFFAOYSA-N |
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CAS DataBase Reference |
105-53-3(CAS DataBase Reference) |
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NIST Chemistry Reference |
Propanedioic acid, diethyl ester(105-53-3) |
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EPA Substance Registry System |
Diethyl malonate (105-53-3) |
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Hazard Codes |
Xi |
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Risk Statements |
36/37/38-36 |
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Safety Statements |
24/25-26 |
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WGK Germany |
1 |
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RTECS |
OO0700000 |
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Autoignition Temperature |
435 °C DIN 51794 |
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Hazard Note |
Irritant |
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TSCA |
Yes |
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HS Code |
29171910 |
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Toxicity |
LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg |
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Chemical Properties |
colourless liquid |
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Chemical Properties |
Diethyl malonate has a faint, pleasant, aromatic odor. |
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Uses |
manufacture of barbiturates. |
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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 |
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Taste threshold values |
Taste characteristics at 50 ppm: sweet and fruity with apple and pineapple nuances. |
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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. |
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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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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 ,98%-->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 |
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Raw materials |
Etanol-->Hydrochloric acid-->Sulfuric acid -->Sodium carbonate-->Sodium cyanide-->Malonic acid-->Chloroacetic acid-->Chloroacetic acid sodium salt-->Cyanoacetic acid-->Disodium hydrogenorthophosphate-->MALONIC ACID DISODIUM SALT |
