33141-66-1

Basic information

• Product Name: ETHYL 4-BROMO-3-HYDROXYBENZOATE
• Synonyms: ETHYL 4-BROMO-3-HYDROXYBENZOATE
• CAS NO: 33141-66-1
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.06996
• Mol File: 33141-66-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 4-BROMO-3-HYDROXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-BROMO-3-HYDROXYBENZOATE(33141-66-1)
• EPA Substance Registry System: ETHYL 4-BROMO-3-HYDROXYBENZOATE(33141-66-1)

Safety Data

• Hazardous Substances Data: 33141-66-1(Hazardous Substances Data)

Usage

General Description

ETHYL 4-BROMO-3-HYDROXYBENZOATE is a chemical compound with the molecular formula C9H9BrO3. It is a derivative of benzoic acid, with a bromine atom and a hydroxyl group attached to the carbon ring. ETHYL 4-BROMO-3-HYDROXYBENZOATE is commonly used in organic synthesis and pharmaceutical research as a building block for the synthesis of various pharmaceuticals and fine chemicals. It is also used as a reagent in the preparation of esters and other organic compounds. The compound is a white to off-white crystalline powder with a melting point of around 127-129°C and is soluble in common organic solvents such as ethanol and acetone. It is important to handle this chemical with caution and follow safety protocols as it may be hazardous if not handled properly.

Upstream product

• 7781-98-8 ethyl-3-hydroxybenzoate 
• 99-06-9 3-Carboxyphenol 
• 64-17-5 ethanol 
• 14348-38-0 4-bromo-3-hydroxybenzoic acid 

Downstream Products

• 540779-35-9 ethyl 4-bromo-3-benzyloxybenzoate 
• 736992-48-6 3-benzyloxy-4-bromobenzaldehyde 
• 540779-36-0 (3-(benzyloxy)-4-bromophenyl)methanol 
• 540779-38-2 ethyl (E)-4-bromo-3-hydroxycinnamate 
• 540779-37-1 ethyl (E)-4-bromo-3-benzyloxycinnamate 
• 540779-39-3 ethyl (E)-4-bromo-3-(3'-tert-butoxycarboxamidopropoxy)cinnamate 
• 540779-43-9 ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-aminopropoxy)cinnamate 
• 540779-42-8 ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate 
• 736992-50-0 (E)-3-[3'-Adamantan-1-yl-2-(3-amino-propoxy)-4'-benzyloxy-biphenyl-4-yl]-acrylic acid ethyl ester 
• 736992-51-1 ethyl (E)-3-[5-(adamant-1-yl)-2-(3-(tert-butoxycarbonylamino)propoxy)-4-hydroxy-2-methylbiphenyl-4-yl]acrylate 
• 540779-41-7 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-(3'-acetamidopropoxy)cinnamate 
• 540779-40-6 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-[(3'-tert-butoxycarboxamido)propoxy]cinnamate 
• 776314-84-2 ethyl 4-bromo-3-{[(methyloxy)methyl]oxy}benzoate 
• 776315-16-3 ethyl 3-{[4-(acetyloxy)butyl]oxy}-4-bromobenzoate 

Relevant articles and documents

Total Synthesis of Benzofuran-Based Aspergillusene B via Halogenative Aromatization of Enones

A novel "non-aromatic pool" synthetic strategy for the synthesis of benzofuran-based natural products via oxidative haloaromatization of enones is reported. This approach is successfully applied in the first total synthesis of the natural product aspergil

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.