ethyl 2-chloro-2-(hydroxyimino)acetate

• ChemBase ID: 64352
• Molecular Formular: C4H6ClNO3
• Molecular Mass: 151.54834
• Monoisotopic Mass: 151.00362074
• SMILES: C(=N\O)(/C(=O)OCC)\Cl
• Canonical SMILES: CCOC(=O)/C(=N/O)/Cl
• InChI: InChI=1S/C4H6ClNO3/c1-2-9-4(7)3(5)6-8/h8H,2H2,1H3/b6-3-
• InChIKey: UXOLDCOJRAMLTQ-UTCJRWHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-chloro-2-(hydroxyimino)acetate; ethyl (2Z)-2-chloro-2-(hydroxyimino)acetate
• IUPAC Traditional name: ethyl 2-chloro-2-(hydroxyimino)acetate; ethyl (2Z)-2-chloro-2-(hydroxyimino)acetate
• Synonyms: Ethyl 2-Chloro-2-(hydroxyimino)acetate; Ethyl chloro(hydroxyimino)ethanoate; 1-Ethyl oxalyl chloride 2-oxime; Ethyl chloro(hydroxyimino)acetate; Ethyl 2-chloro-2-(hydroxyimino)acetate; (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate; 2-Chloro-2-hydroxyiminoacetic acid ethyl ester; 1-乙基乙二酰氯 2-肟; 氯代肟基乙酸乙酯

Database IDs

• CAS Number: 14337-43-0
• MDL Number: MFCD00010209
• Beilstein Number: 606193
• PubChem SID: 162030091; 24854945; 24857601
• PubChem CID: 9576005

CALCULATED PROPERTIES

• Acid pKa: 4.094757
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.36280936
• LogD (pH = 7.4): -1.3131554
• Log P: 1.0150932
• Molar Refractivity: 31.6365 cm^3
• Polarizability: 12.380236 Å^3
• Polar Surface Area: 58.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 70-76 °C(lit.); 70-76°C; 72-77 °C

Safety Information

• Storage Warning: Corrosive/Irritant/Lachrymatory/Moisture Sensitive/Store under Argon/Keep Cold; IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 37/38-41-42/43
• Safety Statements: 22-26-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (T); 95%; 95+%; 97%
• Grade: purum
• Linear Formula: HON=C(Cl)CO2C2H5

DETAILS

Sigma Aldrich - 292621

Application
Reagent used to prepare N-azirdinyloximes which on treatment with scandium triflate (418218) provide dihydro-oxadiazines.1
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 24870

Other Notes
Precursor for the preparation of carbethoxyformonitrile oxide, CEFNO, used for dipolar 1,3-cycloaddition with olefins; this is a versatile method for the cis carboxy-hydroxylation of olefins 1,2,3