1196-29-8

Usage

Uses

Used in Organic Synthesis:
1-(2-HYDROXYPHENYL)ETHAN-1-ONE OXIME is used as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows it to participate in a wide range of reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(2-HYDROXYPHENYL)ETHAN-1-ONE OXIME is used as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure can impart specific biological activities, making it an essential component in the development of new therapeutic agents.
Used in Agrochemical Industry:
1-(2-HYDROXYPHENYL)ETHAN-1-ONE OXIME also finds application in the agrochemical industry, where it is used as a precursor in the synthesis of various pesticides and other crop protection agents. Its ability to form stable derivatives makes it a suitable candidate for the development of effective and environmentally friendly agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals sector, 1-(2-HYDROXYPHENYL)ETHAN-1-ONE OXIME is employed as a raw material for the production of dyes, pigments, and other colorants. Its chemical properties enable it to form stable complexes with various substrates, resulting in vibrant and long-lasting colors.
Overall, 1-(2-HYDROXYPHENYL)ETHAN-1-ONE OXIME is a versatile compound with a wide range of applications across different industries, primarily due to its unique chemical properties and its ability to participate in various organic synthesis processes.

InChI:InChI=1/C8H9NO2/c1-6(9-11)7-4-2-3-5-8(7)10/h2-5,9,11H,1H3/b7-6+

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 33973-15-8 2a,7b-Dihydro-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran 
• 75632-99-4 3-methyl-1,2-benzisoxazole N-oxide 

Downstream Products

• 95-21-6 2-methyl-1,3-benzoxazole 
• 4825-75-6 3-methylbenzo[d]isoxazole 
• 118-93-4 o-hydroxyacetophenone 
• 614-80-2 2-(acetylamino)phenol 
• 1862-88-0 N-methylsalicylamide 
• 261356-06-3 Ru(P(C₆H₅)3)2(C₇H₄CH₃NO)Cl₂ 
• 201941-48-2 [Cu(S₂CN(CH₂C₆H₅)2)(OC₆H₄CCH₃(NOH))] 

Relevant academic research and scientific papers

A novel heterometallic 3d-4f complex with an unusual [MnIV 4Nd4O4] core topology

The complex [Mn4Nd4O4(Me-sao) 6(NO3)4(OMe)4(MeOH)2] (1) with an unprecedented [MnIV4Nd4O4] core topology was synthesized from MnCl2, Nd(NO3) 3 and Me-saoH2 in methanol at basic conditions (Me-saoH2 = 2′-hydroxyacetophenoxime). In 1 MnIV and NdIII ions are bridged by oxido and methoxido ligands to form an unusual topology including two distorted tetrahedral [Nd2Mn 2(μ4-O)] units. 1 crystallizes in the monoclinic space group P21/c with Z = 2 and lattice constants (at 100 K) a = 14.142(4), b = 19.365(5), c = 14.637(4) A, β = 90.32(3)°. Copyright

Zero-field splitting in {MnIII3(μ3-O)} core single-molecule magnets investigated by inelastic neutron scattering and high-field electron paramagnetic resonance spectroscopy

The global zero-field splitting (ZFS) parameters of three, ferromagnetically coupled, μ3-κ3-[XO4]- (X = Cl, Re) capped, manganese(III) oximate single-molecule magnets, [Mn3O(R-sao)3(2,4′-bipyridine)3XO4] [X = Cl, R = Me, Et; X = Re, R = Me; Me-sao = 2-hydroxyphenylethanone oximate(2-)], with crystallographic trigonal symmetry were determined by use of inelastic neutron scattering and high-field/high-frequency electron paramagnetic resonance spectroscopy. ReO4- (O...O ca. 1.7 ?) is larger than ClO4- (O...O ca. 1.4 ?), which allows more parallel alignment of the local ZFS tensors. However, this chemical modification results in concomitant distortions in the equatorial ligand plane. Consistent parametrization of all spectroscopic data was achieved, and effective spin-reversal barriers determined from alternating current susceptibility data were shown to be in good accordance with the energy barriers deduced from spectroscopy.

Moessbauer and electronic spectral studies of iron(III) complexes of oximes.

The hydroxo-bridge complexes of the type [Fe(2)(ligand-H)(4)(OH)(2)] with bidentate nitrogen-oxygen donor ligands, viz. 2-hydroxynaphthaldehydeoxime [hnoH(2)], 2-hydroxyacetphenoneoxime [haoH(2)], salicylaldooxime [SalH(2)], 2-hydroxypropiophenoneoxime [hnoH(2)] have been prepared. All the complexes have been characterized by elemental analysis, magnetic moments, electronic and Moessbauer spectral studies. Moessbauer parameters of the complexes clearly suggest high spin configuration of Fe(III) showing lower magnetic moment to that of the spin only value, i.e. 5.92 BM. It may be due to the antiferromagnetic interaction between Fe(III) centers.

Copper-Catalyzed Three-Component Domino Cyclization for the Synthesis of 4-Aryl-5-(arythio)-2-(trifluoromethyl)oxazoles

A copper-catalyzed oxidative cyclization of oxime, arylthiol, and trifluoroacetic anhydride for the construction of trisubstituted oxazoles has been developed. This transformation combines N-O bond cleavage, C-H functionalization, and intramolecular annulation, providing a practical protocol for the introduction of a trifluoromethyl (-CF3) group at oxazole rings.

Fe(NO3)3·9H2O-catalyzed aerobic oxidative deoximation of ketoximes and aldoximes under mild conditions

A mild, simple process for the effective aerobic oxidative deoximation of a wide range of ketoximes and aldoximes has been developed that utilizes Fe(NO3)3·9H2O as the single catalyst and molecular oxygen as the green oxidant. The environmentally benign protocol provides moderate to excellent yield and broad functional groups tolerance and is a valuable synthetic method for practical applications. According the relevant verification experiment, a plausible mechanism has been proposed.

Calculation and experimental measurement of paramagnetic NMR parameters of phenolic oximate Cu(II) complexes

We present a strategy for predicting the unusual 1H and 13C shifts in NMR spectra of paramagnetic bisoximato copper(ii) complexes using DFT. We demonstrate good agreement with experimental measurements, although 1H-13C correlation spectra show that a combined experimental and theoretical approach remains necessary for full assignment.

Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors

An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields. An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.

Acid Catalyzed Direct-Amidation-Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

A series of 2-methyl-benzoxazoles have been synthesized starting from 2-hydroxy-acetophenones via a one-pot three steps reaction. Hydroxylamonium salt has been used as amidation agent. The reaction occurs with different anions, but the best results is achieved with hydroxylamonium hydrchloride. Despite the number of consecutive stages, the reaction is highly selective. Mild reaction conditions and various solvents can be used, but trifluoroacetic acid is the preferred. Almost, complete recovery of the trifluoroacetic acid can be achieved by vacuum distillation. The role of trifluoroacetic acid, as well as, of the hydroxylamonium salt suggests a cooperative effect leading to high selective formation of 2-methyl-benzoxazoles. Graphical Abstract: One-pot TFA catalyzed synthesis of benzoxazoles starting from 2-hydroxyacetophenones. (Chemical Equation Presented).

Design and synthesis of new of 3-(benzo[d]isoxazol-3-yl)-1-substituted pyrrolidine-2, 5-dione derivatives as anticonvulsants

A series of 3-(benzo[d]isoxazol-3-yl)-N-substituted pyrrolidine-2, 5-dione (7a-7d, 8a-8d, 9a-9c) have been prepared and evaluated for their anticonvulsant activities. Preliminary anticonvulsant activity was performed using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests after intraperitoneal (ip) injection into mice, which are the most widely employed models for early identification of anticonvulsant candidate. The acute neurological toxicity (NT) was determined applying rotorod test. The quantitative evaluation after oral administration in rats showed that the most active was 3-(benzo[d]isoxazol-3-yl)-1-(4-fluorophenyl) pyrrolidine-2, 5-dione (8a) with ED50 values of 14.90 mg/kg. Similarly the most potent in scPTZ was 3-(benzo[d]isoxazol-3-yl)-1-cyclohexylpyrrolidine-2, 5-dione (7d) with ED50 values of 42.30 mg/kg. These molecules were more potent and less neurotoxic than phenytoin and ethosuximide which were used as reference antiepileptic drugs.

Synthesis of ketoximes via a solvent-assisted and robust mechanochemical pathway

A versatile and robust mechanochemical route to ketone-oxime conversions has been established for a broad range of ketones via a simple mortar-pestle grinding method. The relative reactivity of aldehydes vs. ketones under these conditions has also been explored, along with an examination of the possible connection between reactivity and electronic substituent effects.