(Z)-acetaldehyde oxime

Base Information

• Chemical Name: (Z)-acetaldehyde oxime
• CAS No.: 107-29-9
• Molecular Formula: C2H5NO
• Molecular Weight: 59.0678
• Hs Code.: 2928.00
• European Community (EC) Number: 203-479-6
• NSC Number: 4974
• UN Number: 2332
• UNII: IF220J2972
• DSSTox Substance ID: DTXSID401016246
• Nikkaji Number: J4.062B,J1.779.301B
• Wikipedia: Acetaldoxime
• Wikidata: Q2823824
• Metabolomics Workbench ID: 57526
• Mol file: 107-29-9.mol

Synonyms:(Z)-acetaldehyde oxime;(Z)-Acetaldoxime;cis-Acetaldehyde oxime;acetaldehyde, oxime, (1Z)-;(1Z)-acetaldehyde oxime;Acetaldehyde oxime, (1Z)-;Acetaldehyde, oxime, (Z)-;(1Z)-ethanal oxime;5775-72-4;UNII-IF220J2972;107-29-9;IF220J2972;Acetaldehyde, oxime;acetaldehydoxim-;UN 2332;acetaldehydeoxime;E-Acetaldoxime;(NZ)-N-ethylidenehydroxylamine;NA2332;WLN: QNU2;CHEBI:50719;NSC4974;DTXSID401016246;NSC-4974;F13401;A801662;Q2823824

Chemical Property of (Z)-acetaldehyde oxime

Chemical Property:

• Appearance/Colour: white low melting solid or clear liquid
• Vapor Pressure: 13mmHg at 25°C
• Melting Point: 44-46 °C
• Refractive Index: n20/D 1.426(lit.)
• Boiling Point: 114.5 °C at 760 mmHg
• PKA: 11.82±0.10(Predicted)
• Flash Point: 40 °C
• PSA: 32.59000
• Density: 0.969 g/cm³
• LogP: 0.46630
• Storage Temp.: 0-6°C
• Solubility.: 185g/l
• Water Solubility.: soluble
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 59.037113783
• Heavy Atom Count: 4
• Complexity: 25.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Acetaldoxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-10-36-20/22
• Safety Statements: 26-36-24/25-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Oximes
• Canonical SMILES: CC=NO
• Isomeric SMILES: C/C=N\O
• General Description: Acetaldoxime, also known as Ethylidenehydroxylamine or Ethanal oxime, is an aldoxime that serves as a key intermediate in organic synthesis. The second study highlights its role in catalytic dehydration reactions, where it can be selectively converted into nitriles using half-sandwich guanidinate-osmium(II) complexes. This transformation avoids toxic cyanide sources and demonstrates high efficiency, particularly with electron-withdrawing substituents on the catalyst. The findings underscore the utility of acetaldoxime in green and selective synthetic pathways.

Technology Process of (Z)-acetaldehyde oxime

There total 26 articles about (Z)-acetaldehyde oxime 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: 97.0%

cyclohexanone-oxime (100-64-1) + acetaldehyde (75-07-0,9002-91-9) → Acetaldehyde oxime (107-29-9) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

With sulfuric acid; at 4 - 10 ℃; for 2h;

Reference yield: 96.0%

acetaldehyde (75-07-0,9002-91-9) → Acetaldehyde oxime (107-29-9)

Guidance literature:

With hydroxylamine; acetic acid; In water; at 9 ℃; for 0.5h; Temperature; Cooling with ice;

Reference yield: 93.0%

2,2-diacetylbenzo[b]selenophen-3(2H)-one → Acetaldehyde oxime (107-29-9) + 1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone

Guidance literature:

With hydroxylamine hydrochloride; In ethanol; for 3h; Reflux;

DOI:10.1080/00397910902898627

upstream raw materials:

2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate

ethylamine

acetaldehyde

ethanol

Downstream raw materials:

para-chloroacetophenone

1-(2-chlorophenyl)ethanone

2-acetylnitrobenzene

acetamide

Refernces

An environmentally benign synthesis of isoxazolines and isoxazoles mediated by potassium chloride in water

10.1016/j.tetlet.2014.02.118

The study presents an environmentally benign method for synthesizing isoxazolines and isoxazoles via a cycloaddition reaction mediated by potassium chloride (KCl) in water. The key chemicals involved are aldoximes, which are oxidized to nitrile oxides by hypochlorous acid generated in situ from KCl and the oxidant Oxone?. These nitrile oxides then undergo a 1,3-dipolar cycloaddition with alkenes or alkynes to form the desired isoxazolines and isoxazoles. The process is optimized to achieve high yields and involves using KCl as a mediator, Oxone? as the oxidant, and water as the solvent, offering a green and efficient alternative to traditional methods.

Half-Sandwich Guanidinate-Osmium(II) Complexes: Synthesis and Application in the Selective Dehydration of Aldoximes

10.1002/ejic.201501221

This study investigates the synthesis and catalytic applications of a series of novel guanidinate–osmium(II) complexes. The researchers synthesized these complexes by reacting the dimeric precursor [{OsCl(μ-Cl)(?6-p-cymene)}2] with various guanidines (iPrHN)2C=NR. The resulting complexes, [OsCl{?2-(NN')-C(NR)(NiPr)NHiPr}(?6-p-cymene)] (R = Ar), were characterized by various spectroscopic techniques and X-ray diffraction. These complexes were then tested for their catalytic activity in the dehydration of aldoximes to nitriles, a transformation that avoids the use of toxic cyanide sources. The study found that certain complexes, particularly those with electron-withdrawing groups like CF3 and CN, were highly effective, converting a variety of aldoximes into nitriles with high yields and selectivity. The research highlights the potential of osmium-based catalysts in organic synthesis and provides insights into the structure–activity relationship of these complexes.