582-24-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxyacetophenone is used as a pharmaceutical intermediate for the production of various drugs and medications. It plays a crucial role in the synthesis of different pharmaceutical compounds, contributing to the development of new treatments and therapies.
Used in Chemical Synthesis:
2-Hydroxyacetophenone serves as a starting material for the synthesis of several chemical compounds, including:
Enantioselective 1R-phenyl-1,2-ethanediol, which is synthesized in the presence of a rhodium(III) catalyst by asymmetric transfer hydrogenation. 2-Hydroxyacetophenone has potential applications in the pharmaceutical and chemical industries.
Copper(II) complexes of 2-hydroxyacetophenone N-substituted thiosemicarbazones, which are used in various chemical and material science applications.
Chromium, molybdenum, and ruthenium complexes of 2-hydroxyacetophenone Schiff bases, which have potential applications in catalysis and material science.
2-Hydroxyacetophenone-aroyl hydrazone derivatives, which are used for the inhibition of copper corrosion in nitric acid, an important application in the chemical and industrial sectors.

InChI:InChI=1/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H2

Upstream product

• 31517-02-9 anhydrocarboxyglycolic acid 
• 71-43-2 benzene 
• 93-56-1 phenylethane 1,2-diol 
• 3282-32-4 2-diazo-acetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 60-29-7 diethyl ether 
• 107-14-2 chloroacetonitrile 
• 532-27-4 1-chloroacetophenone 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 13831-31-7 Acetoxyacetyl chloride 
• 98-01-1 furfural 
• 96-09-3 styrene oxide 
• 2243-35-8 2-acetoxyacetophenone 

Downstream Products

• 4982-08-5 1-hydroxy-3-phenylpropan-2-one 
• 2243-35-8 2-acetoxyacetophenone 
• 108475-88-3 1,3-diphenylpropan-1-one 
• 93-89-0 benzoic acid ethyl ester 
• 58294-83-0 2,4-diphenyl-but-3-yne-1,2-diol 
• 1231-51-2 2,5-dimethoxy-2,5-diphenyl-[1,4]dioxane 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 90925-48-7 2-phenylbutane-1,2-diol 
• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 380640-28-8 2,5-dimethyl-2,5-diphenyl-[1,4]dioxane 
• 5792-35-8 2,3-dihydroxy-1-phenylpropan-1-one 
• 670-95-1 4-Phenylimidazole 
• 1074-12-0 phenylglyoxal hydrate 

Relevant academic research and scientific papers

Efficient synthesis of benzoylformic acid under mild conditions

A new highly efficient synthesis protocol for benzoylformic acid was developed. Of three steps a key unit involved oxidation using clean aqueous hydrogen peroxide and hydrogen bromide systems.

Origins of Catalyst Inhibition in the Manganese-Catalysed Oxidation of Lignin Model Compounds with H2O2

The upgrading of complex bio-renewable feedstock, such as lignocellulose, through depolymerisation benefits from the selective reactions at key functional groups. Applying homogeneous catalysts developed for selective organic oxidative transformations to complex feedstock such as lignin is challenged by the presence of interfering components. The selection of appropriate model compounds is essential in applying new catalytic systems and identifying such interferences. Here, it was shown by using as an example the oxidation of a model substrate containing a β-O-4 linkage with H2O2 and an in situ-prepared manganese-based catalyst, capable of efficient oxidation of benzylic alcohols, that interference from compounds liberated during the reaction can prevent its application to lignocellulose depolymerisation.

Efficient synthesis of α-hydroxyacetophenone via microwave irradiation of α-bromoacetophenone from acetophenone

Herein, we reported a new and efficient approach starting from acetophenone. In this work, α-hydroxyacetophenone was prepared under microwave irradiation of α-bromoacetophenone which was efficiently prepared by the use of HBr/H2O2 system.

FACILE SYNTHESIS OF α-HYDROXY CARBONYL COMPOUNDS BY ENOLATE OXIDATION WITH DIMETHYLDIOXIRANE

The direct oxidation of enolates with dimethyldioxirane (as a solution in acetone) provides the α-hydroxy derivatives in excellent yield.

Highly selective oxidation of primary and secondary benzylic alcohols by KMnO4/ZrOCl2·8H2O in diethyl ether

Zirconyl chloride octahydrate-potassium permanganate is used for highly selective and efficient oxidation of primary and secondary benzylic alcohols to the corresponding carbonyl compounds under mild condition. Over-oxidation of aldehydes to carboxylic acids and damage to carbon-carbon double bond is not observed by this method.

Regioselective Hydroperoxylation of Aziridines and Epoxides Only with Aqueous Hydrogen Peroxide

A catalyst and organic solvent-free regioselective hydroperoxylation of aziridines and epoxides, including spiroaziridine- and spiroepoxy oxindoles have been explored with commercially available 50% aq. H2O2. This method provides an access to secondary benzylic β-hydroperoxy amines and -alcohols and tertiary 3-hydroperoxy oxindoles. The protocol is also applicable to the less reactive alkyl aziridines. Furthermore, an acid-catalyzed Kornblum-DeLaMare type rearrangement of secondary benzylic hydroperoxide has also been revealed to afford amino- and hydroxyl ketones. (Figure presented.).

Aerobic Direct Dioxygenation of Terminal/Internal Alkynes to α-Hydroxyketones by an Fe Porphyrin Catalyst

We herein report a new synthetic method for the preparation of α-hydroxyketones by the dioxygenation of alkynes. The reaction proceeds at room temperature under the action of Fe porphyrin and pinacolborane under air as a green oxidant to produce α-hydroxyketones. The mild reaction conditions allow chemoselective oxidation with functional group tolerance. Terminal alkynes in addition to internal alkynes are applicable, affording unsymmetrical α-hydroxyketones that are difficult to obtain by any reported dioxygenation of unsaturated C?C bonds.

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides

In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).