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

Description

2-Hydroxyacetophenone, also known as a monohydroxyacetophenone, is an organic compound with the chemical formula C8H8O2. It is an acetophenone derivative in which one of the methyl hydrogens has been replaced by a hydroxy group. This slightly yellow to orange powder is a versatile chemical intermediate with various applications across different industries.

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 
• 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

• 2243-35-8 2-acetoxyacetophenone 
• 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 
• 611-71-2 MANDELIC ACID 
• 24257-90-7 phenyl-glyoxal-bis-(4-nitro-phenylhydrazone) 

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.).

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).

N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air

Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O-containing compounds. Demonstrated here is a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O-atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2.