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Basic Information
| CAS No.: | 553-90-2 |
|---|---|
| Name: | Dimethyl oxalate |
| Article Data: | 132 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn,  Xi
|
| Risk Codes: | 36/38-36-22 |
| Safety: | 26-36/37-24/25-23 |
| Transport Information: | UN 1759 |
| PSA: | 52.60000 |
| LogP: | -0.66760 |
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Synthetic route
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 |
...Expand
- 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
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
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; |
...Expand
- 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
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% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: carbon dioxide With hydrogen; caesium carbonate at 325℃; Glovebox; Stage #2: methanol at 150℃; | 89% |
A
- 553-90-2
Dimethyl oxalate
- 13463-40-6
iron pentacarbonyl
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; |
...Expand
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Dimethyl oxalate
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
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
Risk Statements: 36/38
Safety Statements: 26-36/37-24/25
RIDADR: 1759
WGK Germany: 3
HazardClass: 6.1(b)
PackingGroup: III