| Identification | More | [Name]
2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER | [CAS]
14337-43-0 | [Synonyms]
1-ETHYL OXALYL CHLORIDE 2-OXIME
2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER
AKOS MSC-0743
ALPHA-CHLOROGLYOXALIC ACID ETHYL ESTER OXIME
ETHYL 2-CHLORO-2-(HYDROXYIMINO)ACETATE
ETHYL CHLOROOXIMIDOACETATE
ETHYL CHLOROOXIMINOACETATE
ETHYLCHLOROXIMIDOACETATE
TIMTEC-BB SBB009890
ZERENEX ZX011529
2-CHLORO-2-HYDROXYIMINACETIC ACID ACID ETHYL ESTER
2-chloro-2-hydroxyiminocetic
CHLOROOXIME
2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER 99+%
Ethyl chloro(hydroxyimino)acetic acid
2-(Hydroxyimino)-2-chloroacetic acid ethyl ester
Chloro(hydroxyimino)acetic acid ethyl ester
Ethylchloroximide acetate
Hydroxyiminochloroacetic acid ethyl ester
α-Chloroglyoxalic acid ethyl ester oxime | [EINECS(EC#)]
604-347-4 | [Molecular Formula]
C4H6ClNO3 | [MDL Number]
MFCD00010209 | [Molecular Weight]
151.55 | [MOL File]
14337-43-0.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R42/43:May cause sensitization by inhalation and skin contact .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3335 | [WGK Germany ]
3
| [F ]
10-19-21 | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [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 |
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