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Basic Information
CAS No.: 553-90-2
Name: Dimethyl oxalate
Molecular Structure:
Molecular Structure of 553-90-2 (Dimethyl oxalate)
Formula: C4H6O4
Molecular Weight: 118.089
Synonyms: Ethanedioicacid, dimethyl ester (9CI);Oxalic acid, dimethyl ester (6CI,8CI);Methyl oxalate;NSC 9374;
EINECS: 209-053-6
Density: 1.163 g/cm3
Melting Point: 50-54 °C(lit.)
Boiling Point: 163.5 °C at 760 mmHg
Flash Point: 75 °C
Solubility: 60 g/L (25 °C) in water
Appearance: Colourless crystal
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/38-36-22
Safety: 26-36/37-24/25-23
Transport Information: UN 1759
PSA: 52.60000
LogP: -0.66760
Synthetic route
67-56-1

methanol

144-62-7

oxalic acid

553-90-2

Dimethyl oxalate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid for 1h; Reflux;95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 15h;95%
14724-41-5

diacetato(2,2'-bipyridine)palladium(II)

553-90-2

Dimethyl oxalate

Conditions
ConditionsYield
With 1,4-di(diphenylphosphino)-butane In dichloromethane-d2 at 25℃; Catalytic behavior; Reagent/catalyst; Time;100%
624-91-9

methyl nitrite

201230-82-2

carbon monoxide

A

553-90-2

Dimethyl oxalate

B

10102-43-9

nitrogen(II) oxide

Conditions
ConditionsYield
With 0.5% Pd/C at 100℃; under 375.038 Torr; for 0.000555556h; Pressure; Reagent/catalyst; Temperature; Time;A 98.9%
B n/a
589-57-1

diethyl phosphorylchloridite

17640-25-4

methyl 2,2-dichloro-2-methoxyacetate

A

5781-53-3

monomethyl oxalyl chloride

B

553-90-2

Dimethyl oxalate

C

75-00-3

chloroethane

D

66298-75-7

phosphonic dichloride

E

74813-29-9

methyl phosphonochloridate

F

74813-30-2

ethyl phosphonochloridate

Conditions
ConditionsYield
With iron(III) chloride at 105 - 110℃; for 1.16667h; Product distribution;A n/a
B n/a
C 95%
D n/a
E n/a
F n/a
589-57-1

diethyl phosphorylchloridite

17640-25-4

methyl 2,2-dichloro-2-methoxyacetate

A

553-90-2

Dimethyl oxalate

B

1498-42-6

phosphorodichloridous acid ethyl ester

C

75-00-3

chloroethane

D

66298-75-7

phosphonic dichloride

E

74813-30-2

ethyl phosphonochloridate

F

phosphonic dichloride

Conditions
ConditionsYield
With iron(III) chloride at 105 - 110℃; for 0.833333h; Product distribution;A n/a
B n/a
C 95%
D n/a
E n/a
F n/a
67-56-1

methanol

124-38-9

carbon dioxide

201230-82-2

carbon monoxide

553-90-2

Dimethyl oxalate

Conditions
ConditionsYield
Stage #1: carbon dioxide With cesium bicarbonate; alumina at 325℃; under 18751.9 Torr; for 1h; Glovebox; Inert atmosphere;
Stage #2: carbon monoxide at 325℃; under 15001.5 Torr; for 2h;
Stage #3: methanol at 220℃; under 33753.4 Torr; for 1h; Reagent/catalyst; Pressure; Temperature;
95%
With methyl nitrite; nitrogen(II) oxide; palladium/alumina In water at 100℃; Industry scale;
Stage #1: carbon dioxide; carbon monoxide With alumina; caesium carbonate at 25 - 325℃; under 15001.5 - 18751.9 Torr; Glovebox;
Stage #2: methanol at 150℃; under 26252.6 Torr; Glovebox;
67-56-1

methanol

124-38-9

carbon dioxide

201230-82-2

carbon monoxide

534-17-8

caesium carbonate

A

553-90-2

Dimethyl oxalate

B

15519-28-5

cesium bicarbonate

C

3495-36-1

cesium formate

Conditions
ConditionsYield
Stage #1: carbon dioxide; carbon monoxide; caesium carbonate With silica gel; pyrographite at 325℃; under 15001.5 - 33753.4 Torr;
Stage #2: methanol at 200℃; under 30003 Torr; for 2h; Reagent/catalyst; Temperature; Pressure;
A 95%
B n/a
C 0.8%
67-56-1

methanol

79-37-8

oxalyl dichloride

553-90-2

Dimethyl oxalate

Conditions
ConditionsYield
With pyridine In benzene for 30h;92%
With pyridine In benzene at 20℃; for 30h; Inert atmosphere; Reflux;92%
With pyridine In benzene for 3h; Inert atmosphere; Reflux;92%
67-56-1

methanol

124-38-9

carbon dioxide

553-90-2

Dimethyl oxalate

Conditions
ConditionsYield
Stage #1: carbon dioxide With hydrogen; caesium carbonate at 325℃; Glovebox;
Stage #2: methanol at 150℃;
89%

cis-(methyloxalyl)(methoxycarbonyl)tetracarbonyliron

A

553-90-2

Dimethyl oxalate

13463-40-6

iron pentacarbonyl

C

bis(methoxycarbonyl)tetracarbonyliron

Conditions
ConditionsYield
In dichloromethane-d2 byproducts: CO; introducing a soln. of Fe-complex in CD2Cl2 into NMR tube, maintaining temp. at 28°C under N2; monitoring by (13)C-NMR and gas chromatography;A 15%
B n/a
C 85%
With carbon monoxide In dichloromethane-d2 introducing a soln. of Fe-complex in CH2Cl2 into an autoclave thermostated at 34°C, stirring for 2.5 h under CO pressure; monitoring by (13)C-NMR and gas chromatography, cooling, removal of solvent under vacuum, redissolution in CD2Cl2, monitoring by (13)C-NMR;
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Chemistry

Product Name: Dimethyl oxalate
Synonyms: OXALIC ACID METHYL ESTER;OXALIC ACID BIS-METHYL ESTER;OXALIC ACID DIMETHYL ESTER;CH3OCOCOOCH3;Dimethyl ester of oxalic acid;Ethanedioc acid dimethyl ester;Ethanedioicacid,dimethylester;Ethanedioicaciddimethylester
CAS: 553-90-2
MF: C4H6O4
MW: 118.09
EINECS: 209-053-6
mp:  50-54 °C(lit.)
bp:  163.5 °C(lit.)
density:  1.148 g/mL at 25 °C(lit.)
refractive index:  n20/D 1.39(lit.)
Fp:  167 °F
Merck:  14,6106
BRN:  1071744

Production

Product Categories: Pharmaceutical Intermediates;C2 to C5;Carbonyl Compounds;ESTERS

Toxicity Data With Reference

RTECS  RO2850000 

Consensus Reports

DIMETHYL OXALATE (CAS 553-90-2) Market Research Report 2009

Safety Profile

Hazard Codes:  Xi
Risk Statements:  36/38
Safety Statements:  26-36/37-24/25
RIDADR:  1759
WGK Germany:  3
HazardClass:  6.1(b)
PackingGroup:  III