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| | Ethyl chlorooxoacetate Basic information | | Uses |
| | Ethyl chlorooxoacetate Chemical Properties |
| Melting point | 156-158 °C(Solv: ethanol (64-17-5)) | | Boiling point | 135 °C | | density | 1.222 g/mL at 25 °C(lit.) | | refractive index | 1.416-1.418 | | Fp | 41 °C | | storage temp. | Inert atmosphere,2-8°C | | solubility | soluble in Chloroform | | form | Liquid | | color | Clear | | Specific Gravity | 1.222 | | Water Solubility | Slightly miscible with water. | | Sensitive | Moisture Sensitive | | BRN | 506725 | | InChI | 1S/C4H5ClO3/c1-2-8-4(7)3(5)6/h2H2,1H3 | | InChIKey | OWZFULPEVHKEKS-UHFFFAOYSA-N | | SMILES | CCOC(=O)C(Cl)=O | | CAS DataBase Reference | 4755-77-5(CAS DataBase Reference) | | NIST Chemistry Reference | Chlorooxalic acid, ethyl ester(4755-77-5) | | EPA Substance Registry System | Acetic acid, chlorooxo-, ethyl ester (4755-77-5) |
| Hazard Codes | C,F | | Risk Statements | 34-29-20/21/22-14-10-37-36 | | Safety Statements | 8-45-36/37/39-26-16 | | RIDADR | 2920 | | WGK Germany | 3 | | TSCA | TSCA listed | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29171990 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Eye Dam. 1
Flam. Liq. 3
Skin Corr. 1B
STOT SE 3 |
| | Ethyl chlorooxoacetate Usage And Synthesis |
| Uses | Ethyl oxalyl monochloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. Ethyl oxalyl monochloride acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor.
| | Description | Ethyl chlorooxoacetate has been used as a reactant in the preparation of oxyoxalamide derivatives as epoxide hydrolase inhibitors. | | Chemical Properties | clear liquid | | Uses | Ethyl oxalyl chloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. It acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor. | | Uses | Ethyl chlorooxoacetate can be used for the synthesis of:
- α-keto esters.
- Functionalized 3-pyrolin-2-ones.
- Substituted arylglyoxylic acids via Friedel–Crafts acylation.
- Substituted 9,10-phenanthrenequinones.
- Quinoxalinone derivatives.
| | reaction suitability | reagent type: oxidant | | Synthesis | The general procedure for the synthesis of monoethyl oxalyl chloride from diethyl oxalate was as follows: a mixture of potassium acetate (20 g), water (30 mL) and diethyl oxalate (29.2 g, 0.2 mol) was stirred and reacted for 2 hours at 70-80 °C. Upon completion of the reaction, the reaction mixture was cooled and concentrated to 30 mL. Subsequently, ethanol (50 mL) and ether (150 mL) were added and the mixed solution was filtered to afford 23.61 g of potassium monoethyl oxalate (76% yield). The dried potassium monoethyl oxalate (20.6 g, 0.13 mol) was pre-mixed with diethyl ether (20 mL) in an ice bath and SOCl2 (30 g, 0.25 mol) was added slowly. The reaction mixture was heated under reflux conditions for 15 hours. At the end of the reaction, the resulting white solid of potassium chloride was removed by filtration, the filtrate was separated and the 125-130 °C fraction was collected by distillation to give 12.22 g of monoethyl oxalyl chloride (69% yield). | | References | [1] Gazzetta Chimica Italiana, 1891, vol. 21 I, p. 306
[2] Monatshefte fuer Chemie, 1905, vol. 26, p. 375
[3] Chemische Berichte, 1886, vol. 19, p. 2159
[4] Justus Liebigs Annalen der Chemie, 1889, vol. 254, p. 27
[5] Recueil des Travaux Chimiques des Pays-Bas, 1907, vol. 26, p. 381 |
| | Ethyl chlorooxoacetate Preparation Products And Raw materials |
| Raw materials | Diethyl oxalate-->Potassium Acetate-->Diethyl ether-->Thionyl chloride | | Preparation Products | Ethyl 3,4-dihydro-6-methyl-4-oxothieno[2,3-d]pyrimidine-2-carboxylate-->2-(5-BROMO-2-THIENYL)-3-CHLOROQUINOXALINE-->Oxamic acid sodium salt-->N1-(2,4-Dimethoxybenzyl)-N2-(2-pyridin-2-yl)ethyl)oxalamide-->Oxamic acid-->Ethyl 5-Methyl-1,3,4-thiadiazole-2-carboxylate-->Ethyl thiophene-2-glyoxylate-->Ethyl-4-Chloroindole-2-Carboxylate-->1,3-Bis(4-bromophenyl)propanone-->N-Oxalyl glycine-->Ethyl 2-hydroxyisobutyrate-->Ethyl benzoylformate-->Ethyl [(5-nitro-1,3-thiazol-2-yl)amino](oxo)acetate-->2-Carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone-->3-(4-methylphenyl)-1,2,4-Oxadiazole-5-carboxylic acid ethyl ester-->N-(2-Ethoxy-phenyl)-oxalamic acid ethyl ester |
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