61002-54-8

Basic information

• Product Name: 4-Hydroxyphenyl 4-Methoxyphenyl ketone
• Synonyms: 4-Hydroxyphenyl 4-Methoxyphenyl ketone;4-HYDROXY-4'-METHOXYBENZOPHENONE;(4-hydroxyphenyl)-(4-methoxyphenyl)methanone
• CAS NO: 61002-54-8
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24328
• Mol File: 61002-54-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 413.8°Cat760mmHg
• Flash Point: 160.1°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 1.95E-07mmHg at 25°C
• Refractive Index: 1.595
• Solubility: Chloroform
• CAS DataBase Reference: 4-Hydroxyphenyl 4-Methoxyphenyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenyl 4-Methoxyphenyl ketone(61002-54-8)
• EPA Substance Registry System: 4-Hydroxyphenyl 4-Methoxyphenyl ketone(61002-54-8)

Safety Data

• Hazardous Substances Data: 61002-54-8(Hazardous Substances Data)

Usage

Uses

4-Hydroxy-4''-methoxybenzophenone is an intermediate in the synthesis of Nitromifene Citrate (E/Z mixture) (N496700). Nitromifene Citrate s a non-steroidal estrogen antagonist. It is structurally similar to Tamoxifen (T006000) which is a selective estrogen response modifier (SERM).

Preparation

Preparation by reduction of 4-methoxy- 4?-nitro-benzophenone with stannous chloride and hydrochloric acid, followed by diazotization of the resulting 4-amino-4?-methoxybenzophenone and hydrolysis of the diazonium salt.

InChI:InChI=1/C14H12O3/c1-17-13-8-4-11(5-9-13)14(16)10-2-6-12(15)7-3-10/h2-9,15H,1H3

Upstream product

• 100-66-3 methoxybenzene 
• 99-96-7 4-hydroxy-benzoic acid 
• 67-66-3 chloroform 
• 540-38-5 p-Iodophenol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-95-2 phenol 
• 100-09-4 4-methoxybenzoic acid 
• 76597-40-5 potassium salt of 4-fluoro-4'-hydroxybenzophenone 
• 345-92-6 4,4'-Difluorobenzophenone 
• 25913-05-7 4-fluoro-4'-hydroxybenzophenone 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 52886-92-7 4-methoxy-4'-ethoxybenzophenone 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 94042-63-4 (4-Hydroxy-3,5-bis-pyrrolidin-1-ylmethyl-phenyl)-(4-methoxy-phenyl)-methanone 
• 70036-79-2 (4-hydroxy-3,5-diiodo-phenyl)-(4-methoxy-phenyl)-methanone 
• 671791-58-5 4-(1-(4-methoxyphenyl)-2-phenylbut-1-en-1-yl)phenol 
• 671791-57-4 4-(1-(4-methoxyphenyl)-2-phenylbut-1-en-1-yl)phenol 
• 1403783-44-7 2-(4-(2-(4-chlorophenyl)-2-(cyclohexylmethyl)-1-(4-methoxyphenyl)-cyclopropyl)phenoxy)-N,N-dimethylethanamine 
• 1226012-35-6 (4-(2-(dimethylamino)ethoxy)phenyl)(4-methoxyphenyl)methanone 
• 1005457-04-4 2-(4-hydroxyphenyl)-2-(4-methoxyphenyl)cyclopentanone 

Relevant articles and documents

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N-(2-hydroxybenzylidene)benzohydrazide (HL1), N-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (HL2), or N-(5-bromo-2-hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air-stable reddish-orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier-transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single-crystal X-ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.

An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride

Methanesulfonic acid treated with methanesulfonic anhydride effectively mediates the Fries rearrangement of aryl esters to give hydroxy aryl ketones with high yields. Georg Thieme Verlag Stuttgart · New York.

PROCESS FOR DEMETHYLATING AROMATIC METHYL ETHERS USING 3 -MERCAPTOPROPIONIC ACID

The present application discloses a process for demethylating aromatic methyl ethers by reaction with 3 -mercaptopropionic acid or salts thereof. One preferred example is the demethylation of venlafaxine forming 0 - desmethylvenlafaxine.