2-Hydroxyacetophenone

Base Information

• Chemical Name: 2-Hydroxyacetophenone
• CAS No.: 582-24-1
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29144000
• European Community (EC) Number: 209-480-8
• NSC Number: 171232
• UNII: DQ1N9R01IA
• DSSTox Substance ID: DTXSID7060388
• Nikkaji Number: J20.038G
• Wikidata: Q27103649
• Metabolomics Workbench ID: 67835
• Mol file: 582-24-1.mol

Synonyms:1-phenyl-2-hydroxyethanone;omega-hydroxyacetophenone

Chemical Property of 2-Hydroxyacetophenone

Chemical Property:

• Appearance/Colour: slightly yellow to orange powder
• Vapor Pressure: 0.0161mmHg at 25°C
• Melting Point: 86-89 °C(lit.)
• Refractive Index: 1.551
• Boiling Point: 244.615 °C at 760 mmHg
• PKA: 13.09±0.10(Predicted)
• Flash Point: 100.368 °C
• PSA: 37.30000
• Density: 1.149 g/cm³
• LogP: 0.86160
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Soluble in water, ether, ethanol, chloroform.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

98% ^*data from raw suppliers

2-Hydroxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)CO
• Uses: 2-Hydroxyacetophenone can be used to produce 2-hydroxy-1-phenyl-ethanone-(1)-oxime by heating. It is used as pharmaceutical intermediate. 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.

Technology Process of 2-Hydroxyacetophenone

There total 275 articles about 2-Hydroxyacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → phenylacetaldehyde (122-78-1) + benzaldehyde (100-52-7) + 1-phenyl-2-hydroxyethanone (582-24-1) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With [Co(1,3,6,8,10,13,16,19-octaazabicyclo[6.6.6]eicosane)]Cl₃; dihydrogen peroxide; at 75 ℃; for 24h; under 760.051 Torr; Ionic liquid;

DOI:10.1039/c4nj00120f

Reference yield: 60.0%

phenylethane 1,2-diol (93-56-1) → 1-phenyl-2-hydroxyethanone (582-24-1) + Benzoylformic acid (611-73-4)

Guidance literature:

With modified o-iodoxybenzoic acid; In water; at 60 ℃; for 3h;

DOI:10.1016/S0040-4039(01)02217-1

Reference yield: 53.0%

phenylethane 1,2-diol (93-56-1) → benzaldehyde (100-52-7) + 1-phenyl-2-hydroxyethanone (582-24-1)

Guidance literature:

With calcium hypochlorite; water; aluminum oxide; for 0.00138889h;

DOI:10.1007/s007060170103

upstream raw materials:

anhydrocarboxyglycolic acid

benzene

2-acetoxyacetophenone

phenylethane 1,2-diol

Downstream raw materials:

1-hydroxy-3-phenylpropan-2-one

2-acetoxyacetophenone

1,3-diphenylpropan-1-one

benzoic acid ethyl ester

Refernces

Selenated Schiff bases of 2-hydroxyacetophenone and their palladium(II) and platinum(II) complexes: Syntheses, crystal structures and applications in the Heck reaction

10.1016/j.poly.2007.09.027

The research study on the synthesis, characterization, and application of selenated Schiff bases derived from 2-hydroxyacetophenone and their palladium(II) and platinum(II) complexes. The purpose of the study was to explore the coordination chemistry of these selenated Schiff bases, particularly their potential as catalysts in the Heck reaction, a type of chemical reaction used in organic synthesis. The researchers synthesized selenated Schiff bases L1 and L2, and their complexes with Pd(II) and Pt(II), namely [Pd(L1–H)Cl] (1), [Pt(L1–H)Cl] (2), [Pd(L2–H)Cl] (3), and [PtL2Cl2] (4). The study concluded that these complexes, particularly complex 1, showed promising catalytic activity in the Heck reaction, with an approximately 80% yield in a relatively short reaction time of 14 hours.

Neutral penta-coordinated diorganotin(IV) complexes derived from ortho-aminophenol Schiff bases: Synthesis, characterization and molecular structures

10.1016/j.jorganchem.2010.05.026

The research presents the synthesis, characterization, and molecular structure of six new diorganotin(IV) compounds derived from orthoaminophenol Schiff bases. The study aimed to understand the interactions between organotin(IV) cations and biologically important molecules containing {O, N, O} donor atoms, which is crucial due to the known biological activity of organotin(IV) compounds. The chemicals used in the process include ortho-aminophenol, R2SnO (where R is Me or Ph), and ketones such as acetyl acetone, 2-hydroxyacetophenone, and 2-hydroxy-3-methylacetophenone.

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