N-ethylidenehydroxylamine

• ChemBase ID: 107921
• Molecular Formular: C2H5NO
• Molecular Mass: 59.0672
• Monoisotopic Mass: 59.03711379
• SMILES: C/C=N/O
• Canonical SMILES: C/C=N/O
• InChI: InChI=1S/C2H5NO/c1-2-3-4/h2,4H,1H3
• InChIKey: FZENGILVLUJGJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-ethylidenehydroxylamine; (E)-N-ethylidenehydroxylamine
• IUPAC Traditional name: acetoxime; usaf AM-5; acetaldoxime
• Synonyms: Acetaldoxime, syn + anti; Acetaldehyde oxime, mixture of syn and anti; ACETALDOXIME; aldoxime; acetaldehyde oxime; ethanal oxime; ethylidenehydroxylamine; Acetaldoxime; Acetaldehyde oxime, mixture of syn and anti solution; acetaldehyde oxime; 乙醛肟, syn + anti; 乙醛肟，顺式和反式混合物; 亚乙基羟胺; 乙醛肟，顺式和反式混合物 溶液

Database IDs

• CAS Number: 107-29-9
• EC Number: 203-479-6
• MDL Number: MFCD00002124
• Beilstein Number: 1209252
• Merck Index: 1442
• PubChem SID: 24844978; 24890491; 162095462; 24865485
• PubChem CID: 5324279
• Chemspider ID: 4481813
• Wikipedia Title: Acetaldoxime

CALCULATED PROPERTIES

• Acid pKa: 11.474138
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.37495834
• LogD (pH = 7.4): -0.37255025
• Log P: -0.37248218
• Molar Refractivity: 15.54 cm^3
• Polarizability: 5.855042 Å^3
• Polar Surface Area: 32.59 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 299 g L^-1 in water; miscible in ethanol
• Apperance: clear, colorless to yellow liquid
• Melting Point: 25°C (average of the α and β forms); 43 - 44°C
• Boiling Point: 115 °C(lit.); 115.24°C; 115-117°C
• Flash Point: 104 °F; 131 °F; 36°C(96°F); 40 °C; 40°C; 55 °C
• Density: 0.969; 0.969 g/mL at 25 °C(lit.); 0.97 g cm^-3; 0.98 g/mL at 25 °C
• Refractive Index: 1.4260; n20/D 1.386; n20/D 1.426; n20/D 1.426(lit.)
• Vapor Pressure: 13 mmHg
• Partition Coefficient: -0.13
• Hydrophobicity(logP): -0.144
• pKa: 11.82
• Transition Temperature: solidification point 13-16 °C

Safety Information

• RTECS: AB2975000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 2332; UN2332
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-20/21/22-36; 10-20/22-36; 20/22-36; R:10
• Safety Statements: 26; 26-36/37; S:9-16-29
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Warning
• Main Hazard: Flammable, harmful by ingestion, irritant
• NFPA704:
  

  2

  2

  0

  0
• GHS Hazard statements: H226-H302-H319; H226-H302-H319-H332; H301-H311-H332-H319-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2332 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 95%; 98%; 99%
• Concentration: 50 wt. % in H2O
• Grade: purum
• Linear Formula: CH3CH=NOH

DETAILS

MP Biomedicals - 05205476

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A1002

Packaging
25 g in glass bottle

REFERENCES

• The dimetallated species (n-BuLi, -78^o) can be alkylated at the ɑ-position: Tetrahedron Lett., 25, 263 (1984).
• Nitrile oxides can be generated from other aldoximes in a similar manner. The resulting isoxazolines can readily be reduced to 3-hydroxy ketones.
• Chlorination with NCS: Tetrahedron, 40, 2985 (1984), or chlorine, gives the chloroxime, dehydrochlorination of which generates acetonitrile N-oxide, a reactive 1,3-dipole which undergoes cycloadditions with alkenes providing a one-pot route to 2-isoxazolines (same ref.):