79578-62-4

Basic information

• Product Name: 4-(2-BroMoethoxy)-4'-hydroxybenzophenone
• Synonyms: 4-(2-BroMoethoxy)-4'-hydroxybenzophenone
• CAS NO: 79578-62-4
• Molecular Formula: C₁₅H₁₃BrO₃
• Molecular Weight: 321.16592
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 79578-62-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 139–142°C
• Appearance: /
• CAS DataBase Reference: 4-(2-BroMoethoxy)-4'-hydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-BroMoethoxy)-4'-hydroxybenzophenone(79578-62-4)
• EPA Substance Registry System: 4-(2-BroMoethoxy)-4'-hydroxybenzophenone(79578-62-4)

Safety Data

• Hazardous Substances Data: 79578-62-4(Hazardous Substances Data)

Usage

Chemical Properties

4-(2-BroMoethoxy)-4'-hydroxybenzophenone is White Solid

Uses

4-(2-BroMoethoxy)-4'-hydroxybenzophenone is used in the preparation of estrogen receptor modulators.

Preparation

Preparation by reaction of 4-hydroxybenzoic acid with b-bromophenetole, in solution of a polyphosphoric acid/85% phosphoric acid/zinc chloride mixture. The solution was heated to 50–60°, phosphorous trichloride was added during 1 h and the mixture heated for 20 h at 70° (74%).

Upstream product

• 557-91-5 1,1-Dibromoethane 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 106-93-4 ethylene dibromide 
• 737816-47-6 C₂₁H₂₇BrO₃Si 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-41-2 4-bromo-phenol 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 185223-77-2 [4-(2-Bromo-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methanone 
• 589-10-6 phenoxyethyl bromide 
• 99-96-7 4-hydroxy-benzoic acid 

Downstream Products

• 147323-02-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 110025-28-0 (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol 
• 185223-81-8 (4-{(E)-1-[4-(2-Bromo-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenoxy)-acetic acid 
• 141777-00-6 (E,Z)-4-<1-(p-hydroxyphenyl)-2-phenyl-1-butenyl>phenoxyacetic acid 

Relevant articles and documents

NOVEL COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF

The present disclosure relates to novel compounds having estrogen receptor alpha degradation activity, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions.

Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities

Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of br

Estrogenic triarylethylene acetic acids: Effect of structural variation on estrogen receptor affinity and estrogenic potency and efficacy in MCF-7 cells

Triarylethylenecarboxylic acids exemplified by (E,Z)-2-{4-[1-(p- hydroxyphenyl)-2-phenyl]-1-butenyl}phenoxyacetic acid (8) are a new class of estrogen receptor (ER) ligands capable of tissue selective estrogen agonist and antagonist effects. We report the syntheses of 8 and of analogues incorporating structural features known or anticipated to facilitate ER affinity in triarylethylenes. These studies revealed that the p- hydroxyphenyl moiety, ethylenic bond, and ether oxygen of 8 were all critical for high ER affinity. Although a 1,1-bisphenolic analogue bearing the p- (oxyacetic acid) moiety on its 2-phenyl ring, 12, had low ER affinity, it exhibited estrogenic potency approaching that of 8 in MCF-7 cells. Unlike 8 which was a partial agonist with weak antagonist potency, 12 was a full agonist. A similar profile of potency/efficacy in MCF-7 cells was seen in 9, an ethylenic bond saturated analogue of 8. Growth-promoting effects of 8, 9, and 12 were fully antagonized by the antiestrogen tamoxifen, suggesting that such effects were mediated solely via ER. Thus, our studies in MCF-7 cells have confirmed the estrogenicity of 8 and have enabled identification of two analogues with favorable estrogenic potency and full estrogen efficacy. On this basis, these three (triarylethylene)acetic acids have been selected for more intensive animal studies of their extrareproductive tract estrogenic effects.