ChemicalBook CAS DataBase List 14337-43-0

14337-43-0

Name	2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER
CAS	14337-43-0
EINECS(EC#)	604-347-4
Molecular Formula	C4H6ClNO3
MDL Number	MFCD00010209
Molecular Weight	151.55
MOL File	14337-43-0.mol

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

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 Data

Symbol(GHS)	GHS05,GHS07,GHS08
Signal word	Danger
Hazard statements	H315-H318-H334-H335
Precautionary statements	P261-P280-P305+P351+P338-P342+P311
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 . less more
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 . less more
RIDADR	UN 3335
WGK Germany	3
F	10-19-21
HazardClass	9
HS Code	29280000

Hazard Information

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

459-73-4

2-CHLORO-2-HYDROXYIMINOACETIC ACID ETHYL ESTER

14337-43-0

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

Spectrum Detail

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