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105-53-3

Basic Information
CAS No.: 105-53-3
Name: Diethyl malonate
Molecular Structure:
Molecular Structure of 105-53-3 (Diethyl malonate)
Formula: C7H12O4
Molecular Weight: 160.17
Synonyms: Diethyl propanedioate;Propanedioic acid, diethyl ester;Carbethoxyacetic ester;Dicarbethoxymethane;Methanedicarboxylic acid, diethyl ester;Malonic ester;Malonic acid, diethyl ester;Ethyl Malonate;Propanedioic acid, 1,3-diethyl ester;
EINECS: 203-305-9
Density: 1.06 g/cm3
Melting Point: -50 °C
Boiling Point: 199.3 °C at 760 mmHg
Flash Point: 100 °C
Solubility: Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
Appearance: colourless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25
Transport Information:
PSA: 52.60000
LogP: 0.50270
Synthetic route
130217-49-1

4-[(3-ethoxy-1,3-dioxopropyl)amino]-benzoic acid

A

10256-16-3

N,N'-di-4-carboxyanilide of malonic acid

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 98%
B n/a
101646-18-8

2-carboxymalonanilic acid ethyl ester

A

77317-57-8

N,N'-di-2-carboxyanilide of malonic acid

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 98%
B n/a

[di-μ-(ethoxycarbonyl-(methylene))-bis(tricarbonyl-cobalt) (Co-Co)]

201230-82-2

carbon monoxide

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In hexane High Pressure; soln. of Co2(CO)8 and EtOH placed in autoclave; pressurized (room temp.,50 bar CO); shaken (60 min); IR; gas chromy.;A 98%
B 95%
4270-39-7

4-ethoxymalonanilic acid ethyl ester

A

4270-37-5

N,N'-di-4-ethoxyanilide of malonic acid

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 97%
B n/a

[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-(tricarbonyl-cobalt)-(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

201230-82-2

carbon monoxide

A

15906-55-5, 26534-25-8

Co2(CO)7(PPh3)

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In dichloromethane High Pressure; soln. of cobalt complex and anhyd. ethanol pressurized with CO in autoclave at 25°C and 50 bar for 24 h; IR;A 97%
B 66%
90475-72-2

2-methoxymalonanilic acid ethyl ester

A

7056-72-6

N1,N3-bis(2-methoxyphenyl)malonamide

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a
43038-58-0

2-hydroxy-4-nitromalonanilic acid ethyl ester

A

N,N'-di-2-hydroxy-4-nitroanilide of malonic acid

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a
685-87-0

Diethyl 2-bromomalonate

105-53-3

diethyl malonate

Conditions
ConditionsYield
With bismuth(III) oxide; N-ethyl-N,N-diisopropylamine; para-thiocresol In dichloromethane for 1h; Irradiation;96%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In 2,2,2-trifluoroethanol at 20℃; for 4h; UV-irradiation; Sealed tube; Green chemistry;91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine; 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole In N,N-dimethyl-formamide for 2.5h; Inert atmosphere; Irradiation;87%
159657-36-0

4-carboethoxymalonanilic acid ethyl ester

A

19288-86-9

N,N'-di-4-carboethoxyanilide of malonic acid

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Heating;A 96%
B n/a

[μ2-(ethoxycarbonyl(methylene))-μ2-(carbonyl)-bis(triphenylphosphane-dicarbonyl-cobalt) (Co-Co)]

201230-82-2

carbon monoxide

A

14243-08-4

tricarbonyldi(triphenylphosphine)cobalt(1+) tetracarbonylcobaltate(1-)

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
With ethanol In dichloromethane High Pressure; soln. of cobalt complex and anhyd. ethanol pressurized with CO in autoclave at 25°C and 50 bar for 24 h; IR;A n/a
B 96%
685-87-0

Diethyl 2-bromomalonate

A

632-56-4

tetraethyl ethane-1,1,2,2-tetracarboxylate

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; electrochemical reaction: -1,0 V, 0,1 mol/dm3 Et4NClO4, mercury pool cathode;A 95%
B 5%
With potassium hydrogenphosphate trihydrate; 2,6-di-tert-butyl-4-methyl-phenol In ethanol at 20℃; for 1h; Mechanism; Irradiation; Inert atmosphere; Green chemistry;
685-87-0

Diethyl 2-bromomalonate

189247-71-0

EtTe(CH2)3OH

A

2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;A 71%
B 95%
1071-46-1

hydrogen ethyl malonate

541-41-3

chloroformic acid ethyl ester

A

105-53-3

diethyl malonate

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 95%
B n/a
105-39-5

chloroacetic acid ethyl ester

105-53-3

diethyl malonate

Conditions
ConditionsYield
With sodium ethanolate In ethanol95%
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Specification

The CAS registry number of Diethyl malonate is 105-53-3. The IUPAC name is diethyl propanedioate. In addition, the molecular formula is C7H12O4 and the molecular weight is 160.17. It is also called propanedioic acid, diethyl ester. What's more, it is the diethyl ester of malonic acid. And it is a colourless liquid with an apple-like odour. Besides, it can be used in perfumes. It is also used to synthesize other compounds such as barbiturates and artificial flavourings.

Physical properties about this chemical are: (1)ACD/LogP: 0.70; (2)ACD/LogD (pH 5.5): 0.7; (3)ACD/LogD (pH 7.4): 0.7; (4)ACD/BCF (pH 5.5): 2.02; (5)ACD/BCF (pH 7.4): 2.02; (6)ACD/KOC (pH 5.5): 57.48; (7)ACD/KOC (pH 7.4): 57.48; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 52.6 Å2; (11)Index of Refraction: 1.417; (12)Molar Refractivity: 38.02 cm3; (13)Molar Volume: 151 cm3; (14)Polarizability: 15.07 ×10-24cm3; (15)Surface Tension: 32.3 dyne/cm; (16)Density: 1.06 g/cm3; (17)Flash Point: 100 °C; (18)Enthalpy of Vaporization: 43.55 kJ/mol; (19)Boiling Point: 199.3 °C at 760 mmHg; (20)Vapour Pressure: 0.344 mmHg at 25°C.

Preparation of Diethyl malonate: it can be prepared by reacting the sodium salt of chloroacetic acid with sodium cyanide, followed by base hydrolysis of the resultant nitrile to give the sodium salt malonic acid.

Diethyl malonate can be prepared by reacting the sodium salt of chloroacetic acid with sodium cyanide, followed by base hydrolysis of the resultant nitrile to give the sodium salt malonic acid

Uses of Diethyl malonate: One of the principle uses of this compound is in the malonic ester synthesis. And it can react with 1,2-dichloro-ethane to get cyclopropane-1,1-dicarboxylic acid diethyl ester. This reaction will need reagents K2CO3 and H2O, catalyst (n-Bu)4N(1+)Br(1-) and solvent benzene. The reaction time is 12 hours at reaction temperature of 80 °C. The yield is about 85%.

Diethyl malonate can react with 1,2-dichloro-ethane to get cyclopropane-1,1-dicarboxylic acid diethyl ester

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)CC(=O)OCC
(2)InChI: InChI=1/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
(3)InChIKey: IYXGSMUGOJNHAZ-UHFFFAOYAC

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 6400mg/kg (6400mg/kg)   Biochemical Journal. Vol. 34, Pg. 1196, 1940.
rabbit LD50 skin > 16mL/kg (16mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat LD50 oral 14900uL/kg (14.9mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.