2-Hydroxybenzaldehyde oxime

Base Information

• Chemical Name: 2-Hydroxybenzaldehyde oxime
• CAS No.: 94-67-7
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 29280000
• European Community (EC) Number: 202-353-8
• DSSTox Substance ID: DTXSID9052638
• Wikipedia: Salicylaldoxime
• Mol file: 94-67-7.mol

Synonyms:2-Hydroxybenzaldehyde oxime;94-67-7;2-(hydroxyiminomethyl)phenol;o-hydroxyphenylnitrone;Salicylideneaminoalcohol;2-hydroxybenzaldehyde-oxime;SCHEMBL5348198;DTXSID9052638;AKOS025243587

Chemical Property of 2-Hydroxybenzaldehyde oxime

Chemical Property:

• Appearance/Colour: off-white to light beige crystalline powder
• Vapor Pressure: 0.008mmHg at 25°C
• Melting Point: 59-61 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 256.492 °C at 760 mmHg
• PKA: pK1:1.37(＋1);pK2:9.18;pK3:12.11 (25°C)
• Flash Point: 146.86 °C
• PSA: 52.82000
• Density: 1.42 g/cm³
• LogP: 1.20030
• Storage Temp.: 2-8°C
• Solubility.: sparingly soluble in water, soluble in ethanol, diethyl ether, acetone, benzene.
• Water Solubility.: Slightly soluble in water
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Salicylaldoxime 98+% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Oximes
• Canonical SMILES: C1=CC=C(C(=C1)C=NO)O
• Uses: Salicylaldoxime is an organic compound described by the formula C6H4CH=NOH-2-OH and it is the oxime of salicylaldehyde. This crystalline, colorless solid is a chelator and sometimes used in the analysis of samples containing transition metal ions, with which it often forms brightly colored coordination complexes. As a reagent for copper and nickel. Salicylaldoxime reacts with several metal ions to give intensively coloured complexes which are insoluble in water. The structure of the copper(II), nickel(II) and palladium(II) complexes is shown in Fig. 14 (structure I), and that of the manganese(II), iron(II), cobalt(II) and zinc(II) complexes in Fig. 14 (structure II). The copper(Il) and palladium(II) salicylaldoxime complexes are of importance from an analytical point of view. The complexes precipitated from aqueous media are easily filterable and washable and are weighed after drying at 100°C. The precipitates are of stoichiometric composition. The outstanding stabilities of the copper(II) and palladium(II) complexes make the reagent suitable for the selective determination of these metal ions. These two complexes form quantitatively at low pH values where the complexes of other metal ions do not exist. Besides the gravimetric method, salicylaldoxime is also useful in the volumetric, amperometric and nephelometric determinations of copper and palladium. Salicylaldoxime gives a black precipitate with VOs~ in media containing sulfuric acid; this is soluble in chloroform to give an orange solution. The reaction is specific for vanadium which can thus be detected by this method in the presence of almost all other metals. In neutral medium salicylaldoxime reacts with iron(III) to give a red complex which is soluble in water. The reaction is utilized for the detection of micro amounts of iron.

Technology Process of 2-Hydroxybenzaldehyde oxime

There total 17 articles about 2-Hydroxybenzaldehyde 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: 100.0%

salicylaldehyde (90-02-8) → salicylaldehyde-oxime (94-67-7)

Guidance literature:

With acetic acid; acetone oxime; at 110 ℃; for 1.5h;

Reference yield: 98.0%

2-methyl-benzyl alcohol (89-95-2) → salicylaldehyde-oxime (94-67-7)

Guidance literature:

With TEA; hydroxylamine hydrochloride; In methanol; for 1h;

DOI:10.1016/S0040-4039(01)01876-7

Reference yield: 96.0%

salicylic alcohol (90-01-7) → salicylaldehyde-oxime (94-67-7)

Guidance literature:

With hydroxylamine; oxygen; In ethanol; at 20 ℃; for 0.5h; under 760.051 Torr; Catalytic behavior; Green chemistry;

DOI:10.1007/s13738-017-1131-z

upstream raw materials:

salicylaldehyde

2-Imino-2H-chromene-3-carboxylic acid [1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide

2-(acetoxyiminomethyl)phenol

hexanoylsalicylaldoxime

Downstream raw materials:

2-((2-hydroxybenzylamino)methyl)phenol

salicylonitrile

salicylamide

2-Trimethylsilyloxy-benzylidenoxim-O-trimethylsilyl-ether

Refernces

N-Arylation of nitrogen heterocycles with 2,4-difluoroiodobenzene

10.1016/j.tet.2008.11.036

The research primarily focuses on the arylation reactions of NH-heterocycles, such as pyrazole, 3-(trifluoromethyl)pyrazole, imidazole, and pyrrole, with 2,4-difluoroiodobenzene, facilitated by both copper catalysis and SNAr reactions. The study aims to explore the regioselective reactions and multiple substitutions to synthesize a range of new N-arylated heterocycle derivatives. The reactants include various NH-heterocycles and 2,4-difluoroiodobenzene, with copper catalysts like Cu2O and ligands such as salicylaldoxime utilized in some reactions. The analyses involved the use of 1H, 13C, and 19F NMR spectroscopy, IR spectroscopy, and mass spectrometry to determine the structures and purities of the synthesized compounds, along with X-ray crystallography for certain products to confirm their regiochemistry. The research also includes a Suzuki–Miyaura reaction to extend the utility of the synthesized arylation products.