582-24-1

Basic information

• Product Name: 2-HYDROXYACETOPHENONE
• Synonyms: 2-hydroxy-1-phenyl-ethanon;2-Hydroxy-1-phenylethanone;2-Hydroxyethylphenyl ketone;Acetophenone, 2-hydroxy-;Acetophenone, alpha-hydroxy-;Ethanone, 2-hydroxy-1-phenyl-;Glycolophenone;Methanol, benzoyl-
• CAS NO: 582-24-1
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 209-480-8
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 582-24-1.mol
• Article Data: 323

Chemical Properties

• Melting Point: 86-89 °C(lit.)
• Boiling Point: 126 °C / 12mmHg
• Flash Point: 100.368 °C
• Appearance: Slightly yellow to orange/Powder
• Density: 1.0963
• Vapor Pressure: 0.0161mmHg at 25°C
• Refractive Index: 1.5470 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.09±0.10(Predicted)
• Water Solubility: Soluble in water, ether, ethanol, chloroform.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: 2-HYDROXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYACETOPHENONE(582-24-1)
• EPA Substance Registry System: 2-HYDROXYACETOPHENONE(582-24-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 582-24-1(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow to orange powder

Uses

Different sources of media describe the Uses of 582-24-1 differently. You can refer to the following data:
1. 2-Hydroxyacetophenone can be used to produce 2-hydroxy-1-phenyl-ethanone-(1)-oxime by heating. It is used as pharmaceutical intermediate.
2. 2-Hydroxyacetophenone can be used as a starting material for the synthesis of:Enantioselective 1R-phenyl-1,2-ethanediol in the presence of a rhodium(III) catalyst by asymmetric transfer hydrogenation.Copper(II) complexes of 2-hydroxyacetophenone N-substituted thiosemicarbazones.Chromium, molybdenum, and ruthenium complexes of 2-hydroxyacetophenone Schiff bases.2-Hydroxyacetophenone-aroyl hydrazone derivatives for inhibition of copper corrosion in nitric acid.

Definition

ChEBI: A monohydroxyacetophenone that is acetophenone in which one of the methyl hydrogens has been replaced by a hydroxy group.

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 
• 2243-35-8 2-acetoxyacetophenone 
• 93-56-1 phenylethane 1,2-diol 
• 3282-32-4 2-diazo-acetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 60-12-8 2-phenylethanol 
• 18735-16-5 α,β-diacetoxy-styrene 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 60-29-7 diethyl ether 
• 107-14-2 chloroacetonitrile 
• 532-27-4 1-chloroacetophenone 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 

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 articles and documents

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.

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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.

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.).

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

Nano NiFe2O4 supported phenanthroline Cu(II) complex as a retrievable catalyst for selective and environmentally friendly oxidation of benzylic alcohols

A new magnetically recoverable catalyst consisting of phenanthroline Cu(II) complex supported on nickel ferrite nanoparticles was prepared. The synthesized catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, transmission and scanning electron microscopes, thermogravimetry, energy dispersive X-ray spectroscopy, vibrating sample magnetometry and inductively coupled plasma. Supported copper complex used for solvent free oxidation of 1- phenyl ethanol as a model. Influence of the reaction parameters (kind of oxidant, amount of the catalyst, reaction time, solvent and reaction temperature) were studied. Because of the immobilized complex has been shown to be an efficient heterogeneous catalyst for the selective oxidation of 1-phenyl ethanol to acetophenone (94% yield) by hydrogen peroxide so this green approach extended to other benzylic alcohols. The catalyst had been reused 10 times with no significant loss of catalytic activity. SEM, EDX, XRD, and ICP analysis of reused catalyst indicated that the catalyst was stable after the reaction.