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

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

Used in Pharmaceutical Industry:
4-Hydroxyphenyl 4-Methoxyphenyl ketone is used as an intermediate in the synthesis of Nitromifene Citrate (E/Z mixture) (N496700), a non-steroidal estrogen antagonist. It plays a crucial role in the development of this medication, which is structurally similar to Tamoxifen (T006000), a selective estrogen response modifier (SERM). 4-Hydroxyphenyl 4-Methoxyphenyl ketone contributes to the overall effectiveness of Nitromifene Citrate in treating various medical conditions related to estrogen receptor activity.

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

• 4181-97-9 phenyl 4-methoxybenzoate 
• 100-66-3 methoxybenzene 
• 99-96-7 4-hydroxy-benzoic acid 
• 100-09-4 4-methoxybenzoic acid 
• 108-95-2 phenol 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 74-88-4 methyl iodide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 67-66-3 chloroform 
• 540-38-5 p-Iodophenol 
• 76597-40-5 potassium salt of 4-fluoro-4'-hydroxybenzophenone 

Downstream Products

• 90-96-0 bis(p-methoxyphenyl)methanone 
• 83355-38-8 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[4-(4-methoxy-benzoyl)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 21388-77-2 4-[(4-methoxyphenyl)methyl]phenol 
• 115499-97-3 4-(methoxymethoxy)-4'-methoxybenzophenone 
• 109503-68-6 1-(4-ethoxy-phenyl)-2-bromo-1-(4-methoxy-phenyl)-ethane 
• 60131-72-8 1-(4-ethoxy-phenyl)-1-(4-methoxy-phenyl)-ethene 
• 101169-09-9 4'-ethoxy-4-hydroxy-deoxybenzoin 
• 109654-04-8 1-ethoxy-4-((4-methoxyphenyl)ethynyl)benzene 
• 101594-94-9 4'-ethoxy-4-methoxy-deoxybenzoin 
• 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 
• 157622-86-1 11-[4-(4-Methoxy-benzoyl)-phenoxy]-1-(2-thioxo-thiazolidin-3-yl)-undecan-1-one 
• 157622-85-0 11-[4-(4-Methoxy-benzoyl)-phenoxy]-undecanoic acid 

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.

Analysis of the degradation mechanism of the polyarylene ether anion-exchange membrane for alkaline fuel cell and water-splitting cell applications

Model compounds of benzyltrimethylammonium (BTMA)-modified polyethersulfone, polyetheretherketone, and polyetheroctafluorobiphenyl were synthesized to analyze the degradation mechanism in alkaline fuel cell and water-splitting cell applications. From the

Synthesis on novel Tamoxifen derivatives

The design and synthesis of derivatives of 4-hydroxy-Tamoxifen as potential antagonists of the nuclear receptor LRH-1 are described. Stereoselective McMurry coupling was used to generate the desired internal alkene and a novel method for the synthesis of

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.

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 O-desmethylvenlafaxine.

Tandem catalysis: Access to ketones from aldehydes and arylboronic acids via rhodium-catalyzed addition/oxidation

Direct cross-coupling reactions of aromatic aldehydes with arylboronic acids afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst, acetone and a base. This new reaction, involving a formal aldehyde C-H bond activation, is believed to proceed via a tandem process involving addition of the organometallic species to the aldehyde followed by oxidation by β-hydride transfer.

Tuning the color switching of naphthopyrans via the control of polymeric architectures

A range of polymerisable photochromic naphthopyrans were prepared via the synthesis of an acrylate moiety on either the naphthalene ring (R) and/or the di-aryl (Ar) rings on the 3-position of the naphthopyran. The monomers obtained (NA) were copolymerised

Chiral organic radical cation and dication. A reversible chiroptical redox switch based on stepwise transformation of optically active tetrakis(p-alkoxyphenyl)ethylenes to radical cations and dications

Optically active tetrakis(p-alkoxyphenyl)ethylenes were found to function as reversible chiroptical switches upon redox transformations. Successive one-electron oxidations of chirally modified tetraarylethylene to the corresponding radical cation and then to the dication led to dramatic changes in the electronic absorption and circular dichroism (CD) spectra. The neutral species showed no color or CD in the visible region, while the radical ion was blue in color and exhibited a weak Cotton effect, with the dication green and giving an intense Cotton effect and a sign opposite that observed for the radical cation, at a longer wavelength. Molecular orbital calculations and X-ray crystallographic studies clearly indicate that the olefinic C=C bond is significantly twisted in the dication to minimize the electrostatic and steric repulsions. By lowering the temperature of the dication, the twist around the double bond is more firmly fixed in either P or M chirality to give a stronger Cotton effect and a larger anisotropy (g) factor. Since the spectral changes are completely reversible and reproducible for multiple redox cycles, this chiral redox system can be used in novel redox-driven chiroptical applications, such as molecular switches and memory devices, in which the information is written/read chiroptically in the ternary mode, giving zero CD signal in the neutral form, positive CD for the radical cation, and negative CD for the dication at a given wavelength.

Benzophenone derivatives and related compounds as potent histamine H3-receptor antagonists and potential PET/SPECT ligands

Para-substituted aromatic ethers with benzophenone or related structural elements and a 3-(1H-imidazol-4-yl)propyloxy moiety were prepared by Mitsunobu-type ether synthesis or SNAr reaction. Most of the title compounds possess high antagonist potency in histamine H3-receptor assays in vitro as well as in vivo in mouse CNS following oral administration. After defining 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl phenyl methanone as a new lead, structure-activity relationships were investigated for this new class of compounds. Substitution of the meta′-position of the benzophenone moiety with halogen atoms (e.g., iodine, fluorine) led to compounds with high antagonist potency in vitro as well as in vivo (Ki = 9.3 and 4.3 nM, ED50 = 0.7 and 0.47 mg/kg p.o., 18 and 12, respectively). A receptor profile of several functional in vitro assays for several biogenic amine receptors for the meta′-iodinated derivative demonstrated high selectivity toward the histamine H3 receptor.