Diethyl Malonate

Product Name:

Diethyl malonate

Synonyms:

MALONIC ACID DIETHYL ESTER;MALONIC ESTER;ETHYL MALONATE;Ethyl propanedioate;FEMA 2375;DEM;DICARBETHOXYMETHANE;DIETHYL MALONATE

CAS:

105-53-3

MF:

C7H12O4

MW:

160.17

EINECS:

203-305-9

Product Categories:

Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organics;Organic Building Blocks

Mol File:

105-53-3.mol

Melting point 

-50 °C

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 | DIETHYL MALONATE

refractive index 

n20/D 1.413(lit.)

Fp 

212 °F

storage temp. 

Store below +30°C.

solubility 

20.8g/l (External MSDS)

pka

13.5(at 25℃)

form 

Liquid

explosive limit

0.8-12.8%(V)

Water Solubility 

Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.

JECFA Number

614

Merck 

14,3823

BRN 

774687

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents,

InChIKey

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

CAS DataBase Reference

105-53-3(CAS DataBase Reference)

NIST Chemistry Reference

Propanedioic acid, diethyl ester(105-53-3)

EPA Substance Registry System

Diethyl malonate (105-53-3)

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

24/25-26

WGK Germany 

1

RTECS 

OO0700000

Autoignition Temperature

435 °C DIN 51794

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29171910

Toxicity

LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg

Chemical Properties

colourless liquid

Chemical Properties

Diethyl malonate has a faint, pleasant, aromatic odor.

Uses

manufacture of barbiturates.

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.

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.

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.]

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

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