5298-27-1

Basic information

• Product Name: (2,4-DIHYDROXYPHENYL)(4-METHOXYPHENYL)METHANONE
• Synonyms: (2,4-DIHYDROXYPHENYL)(4-METHOXYPHENYL)METHANONE
• CAS NO: 5298-27-1
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.2427
• Mol File: 5298-27-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 159 °C
• Boiling Point: 453.1°Cat760mmHg
• Flash Point: 175.7°C
• Appearance: /
• Density: 1.296g/cm³
• Vapor Pressure: 7.91E-09mmHg at 25°C
• Refractive Index: 1.623
• PKA: 7.42±0.35(Predicted)
• CAS DataBase Reference: (2,4-DIHYDROXYPHENYL)(4-METHOXYPHENYL)METHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-DIHYDROXYPHENYL)(4-METHOXYPHENYL)METHANONE(5298-27-1)
• EPA Substance Registry System: (2,4-DIHYDROXYPHENYL)(4-METHOXYPHENYL)METHANONE(5298-27-1)

Safety Data

• Hazardous Substances Data: 5298-27-1(Hazardous Substances Data)

Usage

Preparation

preparation by reaction of p-methoxyben-zoic acid (p-anisic acid) with resorcinol,in the presence of Zeolite-H-beta in refluxing p-chlorotoluene (162°) for 3 h, ? with stirring and azeotropic removal of water (55%) ;in the presence of zinc chloride at 160° (Nencki reaction) ;in the presence of zinc chloride and phosphorous oxychloride during 3 h at.

InChI:InChI=1/C14H12O4/c1-18-11-5-2-9(3-6-11)14(17)12-7-4-10(15)8-13(12)16/h2-8,15-16H,1H3

Upstream product

• 46835-94-3 bis(4-methoxy-phenyl)-iodonium cation 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 108-46-3 recorcinol 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 35983-60-9 6-methoxy-3-(4-methoxy-phenyl)-benzofuran-2-carboxylic acid 
• 75226-99-2 [5-methoxy-2-(4-methoxy-benzoyl)-phenoxy]-acetic acid 
• 52814-52-5 3-(4-methoxyphenyl)-6-methoxy-1-benzofuran 
• 143286-73-1 (2-Hydroxy-4-methoxy-phenyl)-(4-methoxy-phenyl)-methanone oxime 
• 6131-38-0 2-hydroxy-4,4'-dimethoxybenzophenone 

Relevant articles and documents

Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives

A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.

Synthese von 4-Alkoxy-2-hydroxyphenylketoximen als Metallextraktions-Reagenzien

The C-Acylation (Friedel-Crafts reaction) of resorcinol with aluminium chloride, the monoetherification in 4-position of the resulting 2,4-dihydroxyphenylketones, and the preparation of oximes (8, 9, 10, 11) from this ketones were investigated.The compounds obtained are characterized by elemental analysis, and the i.r., u.v. and 1H-n.m.r. spectra are discussed.Solubility data of some oximes are determined in water, octane and toluene.The extraction properties for copper-(II)-and iron-(III)-ions are measured by isotope methods in relation to the extragent structure, the extraction time and the pH-range.