736992-48-6

Basic information

• Product Name: 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE
• Synonyms: 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE
• CAS NO: 736992-48-6
• Molecular Formula: C₁₄H₁₁BrO₂
• Molecular Weight: 291.13994
• Mol File: 736992-48-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE(736992-48-6)
• EPA Substance Registry System: 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE(736992-48-6)

Safety Data

• Hazardous Substances Data: 736992-48-6(Hazardous Substances Data)

Usage

General Description

3-(Benzyloxy)-4-bromobenzaldehyde is a chemical compound with the molecular formula C15H13BrO2. It is a yellow to light brown powder and is commonly used in organic synthesis and as an intermediate in the production of pharmaceuticals and other fine chemicals. 3-(BENZYLOXY)-4-BROMOBENZALDEHYDE is known for its aromatic and aldehyde-like odor, and it is primarily used for its ability to react with other compounds in organic reactions. It is important for its role in the synthesis of various drugs and complex organic molecules, making it a valuable compound in the field of chemistry and pharmaceuticals.

Upstream product

• 540779-35-9 ethyl 4-bromo-3-benzyloxybenzoate 
• 7781-98-8 ethyl-3-hydroxybenzoate 
• 33141-66-1 ethyl 4-bromo-3-hydroxybenzoate 
• 99-06-9 3-Carboxyphenol 

Downstream Products

• 540779-40-6 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-[(3'-tert-butoxycarboxamido)propoxy]cinnamate 
• 540779-41-7 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-(3'-acetamidopropoxy)cinnamate 
• 736992-51-1 ethyl (E)-3-[5-(adamant-1-yl)-2-(3-(tert-butoxycarbonylamino)propoxy)-4-hydroxy-2-methylbiphenyl-4-yl]acrylate 
• 736992-50-0 (E)-3-[3'-Adamantan-1-yl-2-(3-amino-propoxy)-4'-benzyloxy-biphenyl-4-yl]-acrylic acid ethyl ester 
• 540779-42-8 ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate 
• 540779-43-9 ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-aminopropoxy)cinnamate 
• 540779-39-3 ethyl (E)-4-bromo-3-(3'-tert-butoxycarboxamidopropoxy)cinnamate 
• 540779-38-2 ethyl (E)-4-bromo-3-hydroxycinnamate 
• 540779-37-1 ethyl (E)-4-bromo-3-benzyloxycinnamate 

Relevant articles and documents

Antagonist analogue of 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2- naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest

The retinoid 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2- naphthalenecarboxylic acid (AHPN) and its active analogues induce cell-cycle arrest and programmed cell death (apoptosis) in cancer cells independently of retinoic acid receptor (RAR) interaction. Its analogue, (E)-4-[3′-(1- adamantyl)-4′-hydroxyphenyl]-3-(3′-acetamidopropyloxy)cinnamic acid (3-A-AHPC) selectively antagonized cell apoptotic events (TR3/nur77/NGFI-B expression and nuclear-to-mitochondrial translocation) but not the proliferative events (cell-cycle arrest and p21WAF1/CIP1 expression) induced by proapoptotic AHPN and its analogues. The syntheses of 3-A-AHPC and proapoptotic (E)-6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-5- chloronaphthalenecarboxylic acid (5-Cl-AHPN) are described. Computational studies on AHPN, AHPC, and three substituted analogues (5-Cl-AHPN, 3-Cl-AHPC, and 3-A-AHPC) suggested reasons for their diametric effects on RAR activation. Density functional theory studies indicated that the 1-adamantyl (1-Ad) groups of the AHPN and AHPC configurations assumed positions that were nearly planar with the aromatic rings of their polar termini. In contrast, in the configurations of the substituted analogues having chloro and 3-acetamidopropyloxy groups, rather than a hydrogen, ortho to the diaryl bonds, the diaryl bond torsion angles increased so that the 1-Ad groups were oriented out of this plane. Docking and molecular dynamics of AHPN, AHPC, and these substituted analogues in the RARγ ligand-binding domain illustrated how specific substituents on the AHPN and AHPC scaffolds modulated the positions and dynamics of the 1-Ad groups. As a result, the position of RARγ helix H12 in forming the coactivator-binding site was impacted in a manner consistent with the experimental effect of each analogue on RARγ transcriptional activation.