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)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

37/38-41-42/43-36/37/38

Safety Statements 

22-26-36/37/39-45-36

RIDADR 

UN 3335

WGK Germany 

3

F 

10-19-21

HazardClass 

9

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

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

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