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292621

Sigma-Aldrich

Ethyl 2-chloro-2-(hydroxyimino)acetate

97%

Synonym(s):

1-Ethyl oxalyl chloride 2-oxime

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About This Item

Linear Formula:
HON=C(Cl)CO2C2H5
CAS Number:
14337-43-0
Molecular Weight:
151.55
Beilstein:
606193
MDL number:
MFCD00010209
UNSPSC Code:
12352100
PubChem Substance ID:
24857601
NACRES:
NA.22

Assay

97%

form

solid

mp

70-76 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)\C(Cl)=N\O

InChI

1S/C4H6ClNO3/c1-2-9-4(7)3(5)6-8/h8H,2H2,1H3/b6-3-

InChI key

UXOLDCOJRAMLTQ-UTCJRWHESA-N

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Application

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

Signal Word

Danger

Hazard Statements

H315,H318,H334,H335

Hazard Classifications

Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Clelia Dallanoce et al.
Bioorganic & medicinal chemistry, 14(13), 4393-4401 (2006-03-15)
The new enantiomerically pure 3-substituted-Delta(2)-isoxazolin-5-yl-ethanolamines (+)-6a/(-)-6b, (-)-6a/(+)-6b, and (+)-7a/(-)-7b, prepared via a 1,3-dipolar cycloaddition-based approach, were tested for their affinity at human beta(1)-, beta(2)-, and beta(3)-adrenergic receptor (beta-AR) subtypes stably expressed in CHO cells. The corresponding 3-isopropenyl derivatives (+)-5a/(-)-5b, (-)-5a/(+)-5b
Enantiopure stereoisomeric homologues of glutamic acid: chemoenzymatic synthesis and assignment of their absolute configurations.
Roda G, et al.
Tetrahedron Asymmetry, 15(19), 3079-3090 (2004)
Tetrahedron Letters, 47, 9029-9029 (2006)
An improved synthesis of enantiomerically pure CIP-AS, a potent and selective AMPA-kainate receptor agonist.
Conti P, et al.
Tetrahedron Asymmetry, 12(9), 1363-1367 (2001)
Occupational allergic contact dermatitis from ethyl chloro oximido acetate.
B M Hausen
Contact dermatitis, 27(4), 277-278 (1992-10-01)

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