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| | 2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER Basic information |
| Product Name: | 2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER | | Synonyms: | Ethyl 2-chloro-2-(hydroxyimino)acetate 97%;(2Z)-2-chloro-2-hydroximino-acetic acid ethyl ester;(2Z)-2-chloro-2-hydroxyiminoacetic acid ethyl ester;ETHYLCHLOROXIMIDOACETATE;Ethyl 2-chloro-2-(hydroxyimino)ethanoate;2-chloro-2-hydroximino-acetic acid ethyl ester;ethyl (2Z)-2-chloro-2-hydroxyiminoacetate;ethyl (2Z)-2-chloro-2-hydroxyimino-acetate | | CAS: | 14337-43-0 | | MF: | C4H6ClNO3 | | MW: | 151.55 | | EINECS: | 604-347-4 | | Product Categories: | API;Acids and Derivatives | | Mol File: | 14337-43-0.mol |  |
| | 2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER Chemical Properties |
| Melting point | 70-76 °C (lit.) | | Boiling point | 230.5±23.0 °C(Predicted) | | density | 1.36±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 7.60±0.10(Predicted) | | color | White to Almost white | | Sensitive | Moisture Sensitive/Lachrymatory | | BRN | 606193 | | InChI | InChI=1S/C4H6ClNO3/c1-2-9-4(7)3(5)6-8/h8H,2H2,1H3 | | InChIKey | UXOLDCOJRAMLTQ-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)C(Cl)=NO | | CAS DataBase Reference | 14337-43-0(CAS DataBase Reference) |
| | 2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER Usage And Synthesis |
| Chemical Properties | off-white solid | | Uses | Ethyl 2-chloro-2-(hydroxyimino)acetate has been used:
- in the preparation of (+)-and ()-Δ2-isoxazolines
- in the synthesis of CIP-AS (), a chiral amino acid structurally related to glutamic acid, potential agonist at the ionotropic (±±)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA)-kainate receptors
- to generate ethoxycarbonylformonitrile oxide, in situ by treatment with sodium bicarbonate
- to prepare N-azirdinyloximes which on treatment with scandium triflate (418218) provide dihydro-oxadiazines
| | Synthesis | General procedure for the synthesis of ethyl chlorooxime acetate from ethyl 2-aminoacetate: ethyl aminoacetate (5 g, 48.53 mmol) was dissolved in water (5 ml) to form a solution. To this solution, concentrated hydrochloric acid (8 ml) was slowly added at 0°C, followed by a mixture of sodium nitrite (NaNO2, 4.91 g, 145.6 mmol) and water (5 ml). The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum to give ethyl chloroxime acetate (1.5 g, 20% yield) as a white solid.1H NMR (400 MHz, CDCl3): δ 1.37-1.41 (t, J = 7.2 Hz, 3H); 4.38-4.43 (q, J = 7.2 Hz, 2H). 9.59-9.61 (m, 1H). | | References | [1] Patent: WO2009/118759, 2009, A2. Location in patent: Page/Page column 113
[2] Journal of Heterocyclic Chemistry, 1964, vol. 1, p. 280 - 287
[3] Patent: CN108440435, 2018, A. Location in patent: Paragraph 0024; 0027; 0029; 0038 |
| | 2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER Preparation Products And Raw materials |
| Raw materials | Carbonocyanidic acid, ethyl ester, N-oxide-->Acetic acid, 2-(hydroxyimino)-, ethyl ester, (2E)--->ETHYL 2-(HYDROXYIMINO)-3-OXOBUTANOATE-->Ethyl 2-chloroacetoacetate-->Isoamyl nitrite-->Sodium nitrite-->ethyl glycinate-->Glycine ethyl ester hydrochloride-->Ethyl nitroacetate-->Sodium bicarbonate | | Preparation Products | Acetic acid, 2-chloro-2-nitro-, ethyl ester-->ETHYL 5-TRIBUTYLSTANNANYLISOXAZOLE-3-CARBOXYLATE-->ETHYL 5-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLATE-->3-(ethoxycarbonyl)-1,2-oxazole-5-carboxylic acid-->3-Isoxazolecarboxylic acid, 5-ethoxy-4,5-dihydro-, ethyl ester-->ethyl 5-pyridin-2-yl-4,5-dihydroisoxazole-3-carboxylate |
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