1470-57-1

Basic information

• Product Name: 2-HYDROXY-5-METHYLBENZOPHENONE
• Synonyms: (2-Hydroxy-5-methylphenyl)phenylmethanone;2-Benzoyl-4-methylphenol;5-Methyl-2-hydroxybenzophenone;Benzophenone, 2-hydroxy-5-methyl-;Methanone, (2-hydroxy-5-methylphenyl)phenyl-;2'-HYDROXY 5'-METHYL BENZOPHENONE;2-HYDROXY-5-METHYLBENZOPHENONE;RARECHEM FH 1L 0064
• CAS NO: 1470-57-1
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• EINECS: 216-002-1
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 1470-57-1.mol
• Article Data: 51

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 312.08°C (rough estimate)
• Flash Point: 144.8 °C
• Appearance: yellow crystalline powder
• Density: 1.1035 (rough estimate)
• Vapor Pressure: 4.44E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 8.24±0.43(Predicted)
• CAS DataBase Reference: 2-HYDROXY-5-METHYLBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-5-METHYLBENZOPHENONE(1470-57-1)
• EPA Substance Registry System: 2-HYDROXY-5-METHYLBENZOPHENONE(1470-57-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1470-57-1(Hazardous Substances Data)

Usage

Description

2-HYDROXY-5-METHYLBENZOPHENONE is a yellow crystalline powder that serves as a general reagent in the synthesis of various compounds, particularly those with anti-bacterial and anti-fungal properties.

Uses

Used in Pharmaceutical Industry:
2-HYDROXY-5-METHYLBENZOPHENONE is used as a reagent for the synthesis of anti-bacterial and anti-fungal agents, contributing to the development of new medications to combat bacterial and fungal infections.
Used in Chemical Synthesis:
2-HYDROXY-5-METHYLBENZOPHENONE is utilized as a general reagent in chemical synthesis, playing a crucial role in the production of various compounds with potential applications in different industries.

Preparation

Preparation by condensation of benzotrichloride with p-cresol, ? in the presence of aluminium chloride in carbon disulfide for 2 h (75%). The 6,12-diphenyl-2,8-dimethyl-6,12-epoxy-6H,12H-dibenzo[b,f] dioxocin, an intermediate compound, was also formed under these conditions (29%). This “dioxocin”, by hydrolysis with concentrated sulfuric acid at r.t., gave the expected ketone (91%); ? in the presence of aqueous sodium hydroxide in a water bath for 4 h (33%) or in 32–40% aqueous sodium hydroxide at 70–80° (67%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1924, 1973 DOI: 10.1021/jo00950a030

InChI:InChI=1/C14H12O2/c1-10-7-8-13(15)12(9-10)14(16)11-5-3-2-4-6-11/h2-9,15H,1H3

Upstream product

• 106-44-5 p-cresol 
• 614-34-6 p-cresyl benzoate 
• 98-88-4 benzoyl chloride 
• 622-60-6 1-ethoxy-4-methylbenzene 
• 17852-28-7 2-amino-5-methylbenzophenone 
• 98-07-7 Benzotrichlorid 
• 65849-33-4 (2-Brom-4-methylphenyl)-benzoat 
• 130333-02-7 [5-Methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-phenyl-methanone 
• 916988-26-6 4-Methyl-benzoic acid 2-benzoyl-4-methyl-phenyl ester 
• 65-85-0 benzoic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 1483-73-4 diphenyliodonium bromide 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 108437-84-9 2-hydroxy-5-methyl-benzophenone-(O-methyl-seqtrans-oxime ) 
• 855195-71-0 2-ethoxy-5-methyl-benzophenone 
• 6723-09-7 2-hydroxy-3-bromo-5-methyl benzophenone 
• 89-56-5 5-Methylsalicylic acid 
• 716-96-1 2-benzyl-4-methylphenol 
• 64712-30-7 2-hydroxy-5-methylbenzophenone (E) oxime 
• 108437-81-6 2-hydroxy-5-methyl-benzophenone-seqcis-oxime 
• 859820-09-0 2-benzoyl-4-methyl-4,6-dinitro-cyclohexa-2,5-dienone 
• 135564-55-5 2-acetoxy-5-methyl-benzophenone 
• 77347-19-4 2,6-dibenzoyl-4-methylphenol 
• 4072-13-3 (2-methoxy-5-methylphenyl)phenylmethanone 
• 62665-76-3 C₁₈H₁₉NO₃ 
• 97781-15-2 4-Methyl-2-{phenyl-[(E)-propylimino]-methyl}-phenol 
• 33257-85-1 6-methyl-3,4-diphenyl-2H-chromen-2-one 

Relevant articles and documents

Synthesis and crystal structure of 2-benzoyl-4-methyl phenyl benzoate

The crystal structure of the title compound, C21H 16O3, has been determined. The compound crystallizes in triclinic space group PI with cell parameters a = 9.2240(9) A, b = 9.8050(8) A, c = 10.1610(11) A, α = 94.749(6)°, β = 112.544(4)°, γ = 102.145(6)° and Z = 2. The structure exhibits both intra and intermolecular interactions of the type C-H...O. The intermolecular interaction between the molecules form centrosymmetric dimers.

Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones

The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.

Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.