2-Chloro-2-hydroxyiminoacetic acid ethyl ester

Base Information

• Chemical Name: 2-Chloro-2-hydroxyiminoacetic acid ethyl ester
• CAS No.: 14337-43-0
• Molecular Formula: C4H6ClNO3
• Molecular Weight: 151.55
• Hs Code.: 29280000
• Wikidata: Q76324808
• Mol file: 14337-43-0.mol

Synonyms:2-chloro-2-hydroxyiminoacetic acid ethyl ester;chloro oxime;ethyl chloro oximido acetate

Chemical Property of 2-Chloro-2-hydroxyiminoacetic acid ethyl ester

Chemical Property:

• Appearance/Colour: Brown crystal
• Vapor Pressure: 0.0124mmHg at 25°C
• Melting Point: 70-76 °C(lit.)
• Refractive Index: 1.48
• Boiling Point: 230.5 °C at 760 mmHg
• PKA: 7.60±0.10(Predicted)
• Flash Point: 93.2 °C
• PSA: 58.89000
• Density: 1.36 g/cm³
• LogP: 0.57600
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive/Lachrymatory
• Solubility.: soluble in Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 151.0036207
• Heavy Atom Count: 9
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-Chloro-2-(hydroxyimino)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 37/38-41-42/43-36/37/38
• Safety Statements: 22-26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=NO)Cl
• Isomeric SMILES: CCOC(=O)/C(=N/O)/Cl
• Uses: Ethyl 2-chloro-2-(hydroxyimino)acetate has been used:in the preparation of (+)-and (?)-Δ2-isoxazolinesin 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 receptorsto generate ethoxycarbonylformonitrile oxide, in situ by treatment with sodium bicarbonateto prepare N-azirdinyloximes which on treatment with scandium triflate (418218) provide dihydro-oxadiazines

Technology Process of 2-Chloro-2-hydroxyiminoacetic acid ethyl ester

There total 23 articles about 2-Chloro-2-hydroxyiminoacetic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

ethyl (2E)‐2‐(hydroxyimino)acetate (31767-15-4) → ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0)

Guidance literature:

With chlorine; In dichloromethane;

Reference yield: 54.0%

glycine ethyl ester hydrochloride (623-33-6) → ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at -5 ℃;

DOI:10.1021/jo00151a017

Reference yield: 36.0%

C4H5ClNO4(1-)*H4N(1+) (34428-17-6) → ethyl chloronitroacetate (14011-27-9) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0)

Guidance literature:

With thionyl chloride; In diethyl ether; for 0.25h; Heating;

DOI:10.1007/BF00953447

upstream raw materials:

nitroacetic acid ethyl ester

ethyl 2-(hydroxyimino)acetate

glycine ethyl ester hydrochloride

ethyl 2-chloro-3-oxo-butyrate

Downstream raw materials:

4,5-diphenyl-4,5-dihydro-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester

ethyl hydroxyimino(1,2,4-imidazol-1-yl)acetate

2-Chloro-1-hydroxy-4-oxo-azetidine-2-carboxylic acid ethyl ester

[(Z)-Hydroxyimino]-(4-methoxy-phenyl)-acetic acid ethyl ester

Refernces

• 1、 Quadrelli, Paolo,Bovio, Bruna,Piccinini, Achille,Caramella, Pierluigi,De Sarlo, Francesco,Machetti, Fabrizio. "Conversion of a nitrosocarbonyl hetero Diels-Alder cycloadduct to useful isoxazoline-carbocyclic aminols". . p. 10679 - 10684. Retrieved 2009.
• 2、 Egorova, Anna,Ekins, Sean,Jahn, Birgit,Kazakova, Elena,Makarov, Vadim,Schmidtke, Michaela. "Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses". . . Retrieved 2019/12/28.
• 3、 Kesornpun, Chatchai,Aree, Thammarat,Mahidol, Chulabhorn,Ruchirawat, Somsak,Kittakoop, Prasat. "Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles". supporting information. p. 3997 - 4001. Retrieved 2016/03/19.