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

Chemical Properties

yellow crystalline powder

Uses

2-?Hydroxy-?5-?methylbenzophenone is a general reagent used in the synthesis of anti-bacterial and anti-fungal agents.

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 
• 98-88-4 benzoyl chloride 
• 17852-28-7 2-amino-5-methylbenzophenone 
• 98-07-7 Benzotrichlorid 
• 614-34-6 p-cresyl benzoate 
• 65849-33-4 (2-Brom-4-methylphenyl)-benzoat 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 1483-73-4 diphenyliodonium bromide 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 10602-37-6 1,1,3,3-tetraethoxy-2-methyl-propane 
• 99564-79-1 1-phenyl-1,3-bis(trimethylsilyloxy)-1,3-butadiene 
• 6627-55-0 2-bromo-p-cresol 
• 119-53-9 2-hydroxy-2-phenylacetophenone 

Downstream Products

• 108437-84-9 2-hydroxy-5-methyl-benzophenone-(O-methyl-seqtrans-oxime ) 
• 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 
• 130155-77-0 2-(1,1-dimethylprop-2-ynyloxy)-5-methyl-benzophenone 
• 81393-19-3 Carbamic acid 2-benzoyl-4-methyl-phenyl ester 
• 97781-13-0 4-Methyl-2-{[(E)-phenethylimino]-phenyl-methyl}-phenol 

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.

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.

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.