292621

Sigma-Aldrich

Ethyl 2-chloro-2-(hydroxyimino)acetate

97%

Synonym(s):
1-Ethyl oxalyl chloride 2-oxime
Linear Formula:
HON=C(Cl)CO2C2H5
CAS Number:
Molecular Weight:
151.55
Beilstein/REAXYS Number:
606193
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

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

Packaging

5, 25 g in glass bottle

Signal Word

Danger

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3335

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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)
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)
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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