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:

1,3-diphenylpropan-1-one

benzoic acid ethyl ester

2,4-diphenyl-but-3-yne-1,2-diol

2,5-dimethoxy-2,5-diphenyl-[1,4]dioxane

Refernces

• 1、 Barbieri, Alessia,Kasper, Johann B.,Mecozzi, Francesco,Lanzalunga, Osvaldo,Browne, Wesley R.. "Origins of Catalyst Inhibition in the Manganese-Catalysed Oxidation of Lignin Model Compounds with H2O2". . p. 3126 - 3133. Retrieved 2019.
• 2、 Xu, Haoshu,Wu, Xueping,Ding, Yun,Peng, Chengjun,Peng, Xinhua. "Efficient synthesis of α-hydroxyacetophenone via microwave irradiation of α-bromoacetophenone from acetophenone". . p. 3185 - 3187. Retrieved 2015.
• 3、 Firouzabadi,Fakoorpour,Hazarkhani. "Highly selective oxidation of primary and secondary benzylic alcohols by KMnO4/ZrOCl2·8H2O in diethyl ether". . p. 3859 - 3862. Retrieved 2001.
• 4、 Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey. "Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide". supporting information. . Retrieved 2021/06/03.
• 5、 Bez, Ghanashyam,Gogoi, Achinta,Pasupuleti, Bala Gangadhar. "Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH". . p. 589 - 597. Retrieved 2021/09/28.