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Cas Database

Name	DIMETHYL OXALATE	EINECS	209-053-6
CAS No.	553-90-2	Density	1.163 g/cm³
PSA	52.60000	LogP	-0.66760
Solubility	60 g/L (25 °C) in water	Melting Point	50-54 °C(lit.)
Formula	C₄H₆O₄	Boiling Point	163.5 °C at 760 mmHg
Molecular Weight	118.089	Flash Point	75 °C
Transport Information	UN 1759	Appearance	Colourless crystal
Safety	26-36/37-24/25-23	Risk Codes	36/38-36-22
Molecular Structure		Hazard Symbols	Xn, Xi
Synonyms	Ethanedioicacid, dimethyl ester (9CI);Oxalic acid, dimethyl ester (6CI,8CI);Methyl oxalate;NSC 9374;	Article Data	132

DIMETHYL OXALATE Synthetic route

: 67-56-1
methanol

: 144-62-7
oxalic acid

: 553-90-2
Dimethyl oxalate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 67-56-1
methanol

: 124-38-9
carbon dioxide

: 201230-82-2
carbon monoxide

: 553-90-2
Dimethyl oxalate

Conditions

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 67-56-1
methanol

: 79-37-8
oxalyl dichloride

: 553-90-2
Dimethyl oxalate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

DIMETHYL OXALATE Chemical Properties

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

DIMETHYL OXALATE Production

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

DIMETHYL OXALATE Toxicity Data With Reference

RTECS RO2850000

DIMETHYL OXALATE Consensus Reports

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

DIMETHYL OXALATE 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

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