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 It is an acetophenone derivative in which one of the methyl hydrogens has been replaced by a hydroxy group.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

• 60-29-7 diethyl ether 
• 107-14-2 chloroacetonitrile 
• 93-56-1 phenylethane 1,2-diol 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 817-87-8 ethyl azidocarbonate 
• 64-17-5 ethanol 
• 107-43-7 betaine 
• 115152-08-4 2-phenyl-2-oxoethyl trifluoroacetate 
• 6362-66-9 4-phenyl-dihydro-furan-2,3-dione 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 859950-63-3 1,5-dichloro-1,5-diphenyl-penta-1,3-diene 
• 10028-15-6 ozone 
• 100-42-5 styrene 

Downstream Products

• 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) 
• 4217-62-3 1,1-diphenyl-1,2-ethanediol 
• 31787-73-2 2-isopropyl-4-phenyl-1H-imidazole 

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.).

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%.