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108-59-8

Basic Information
CAS No.: 108-59-8
Name: Propanedioicacid, 1,3-dimethyl ester
Article Data: 112
Cas Database
Molecular Structure:
Molecular Structure of 108-59-8 (Propanedioicacid, 1,3-dimethyl ester)
Formula: C5H8O4
Molecular Weight: 132.116
Synonyms: Malonicacid, dimethyl ester (6CI,8CI);Propanedioic acid, dimethyl ester (9CI);Dimethyl 1,3-propanedioate;Dimethyl propanedioate;Methylmalonate;NSC 620046;Dimethyl Malonate (DMM);Dimethyl malonate;
EINECS: 203-597-8
Density: 1.156 g/cm3
Melting Point: -62 °C(lit.)
Boiling Point: 177.1 °C at 760 mmHg
Flash Point: 90 °C
Solubility: negligible
Appearance: liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 52.60000
LogP: -0.27750
Synthetic route
67-56-1

methanol

141-82-2

malonic acid

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
zirconium(IV) oxide; molybdenum at 84.85℃; for 6h; Esterification;95%
iodine for 15h; Heating;94%
141-82-2

malonic acid

616-38-6

carbonic acid dimethyl ester

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid at 80 - 85℃; for 2h; Neat (no solvent);99.8%
16695-14-0

Malonic acid monomethyl ester

79-22-1

methyl chloroformate

A

108-59-8

malonic acid dimethyl ester

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 95%
B n/a
16695-14-0

Malonic acid monomethyl ester

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
95%
Co2 (CO)8

Co2 (CO)8

96-34-4

methyl chloroacetate

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With sodium methylate In methanol91%
With sodium hydroxide In methanol87%
13750-34-0

N--p-toluolsulfonamid

A

84274-88-4

N--p-toluolsulfonamid

B

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With sodium methylate; malonic acid dimethyl ester In methanol for 8h; Ambient temperature;A 90%
B 84%
96-34-4

methyl chloroacetate

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With potassium methanolate In methanol; Co2 (CO)890%
67-56-1

methanol

dicobalt(η2-(C,C)-ketene)(CO)7

A

79-20-9

acetic acid methyl ester

B

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With carbon monoxide In methanol Carbonylation at 50 atm.;A 77%
B 7%
109-84-2

2-hydroxyethylhydrazine

dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

A

7,7-dimethyl-2,3,7,7a-tetrahydropyrazolo<5,1-b>oxazole

B

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In methanol for 8h; Heating;A 75%
B 73%
67-56-1

methanol

75-09-2

dichloromethane

201230-82-2

carbon monoxide

A

109-87-5

Dimethoxymethane

B

79-20-9

acetic acid methyl ester

C

6290-49-9

methyl methoxyacetate

D

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis;A 8%
B n/a
C 3%
D 74.5%
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio;A 8%
B n/a
C 3%
D 74.5%
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h;A 1.2 % Chromat.
B 7.5 % Chromat.
C 1.9 % Chromat.
D 28.8 % Chromat.
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

Dimethyl malonate, with the CAS NO.108-59-8, is a diester derivative of malonic acid. It is a common reagent for organic synthesis. It is used in the malonic ester synthesis. It is also called Dimethyl ester of malonic acid; Dimethyl propanedioate; dimethyl1,3-propanedioate; dimethylpropanedioate; MALONIC ACID,BIS-METHYL ESTER; MALONIC ACID DIMETHYL ESTER; METHYL MALONATE. Dimethyl malonate should be stored in a cool, dry place. Keep container closed when not in use.

Physical properties about Dimethyl malonate are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -0.36; (3)ACD/LogD (pH 7.4): -0.36; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 15.19; (7)ACD/KOC (pH 7.4): 15.18; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.402; (11)Molar Refractivity: 28.763 cm3; (12)Molar Volume: 118.034 cm3; (13)Polarizability: 11.403 10-24cm3; (14)Surface Tension: 31.9130001068115 dyne/cm; (15)Density: 1.119 g/cm3; (16)Flash Point: 90 °C; (17)Enthalpy of Vaporization: 41.338 kJ/mol; (18)Boiling Point: 177.071 °C at 760 mmHg; (19)Vapour Pressure: 1.05900001525879 mmHg at 25°C

You can still convert the following datas into molecular structure
(1)InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3;
(2)InChIKey=BEPAFCGSDWSTEL-UHFFFAOYSA-N;
(3)SmilesC(C(OC)=O)C(OC)=O;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.
rat LD50 oral 5331mg/kg (5331mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.