104224-68-2

Basic information

• Product Name: 2-(1-Adamantyl)-4-bromophenol
• Synonyms: 2-(1-Adamantyl)-4-bromophenol (Adapalene);2-(1-Adamantyl)-4-br;4-BROMO-2-ADAMANTYL PHENOL;(2-ADAMANTYL)-4-BROMOPHENOL;2-(1-ADAMANTYL)-4-BROMOPHENOL;2-(Adamantan-1-yl)-4-bromophenol;2-ADAMANTANE-4-BROMOANISOLE;2-(Adamantan-1-yl)-4-bromophenol 98%
• CAS NO: 104224-68-2
• Molecular Formula: C₁₆H₁₉BrO
• Molecular Weight: 307.23
• Product Categories: blocks;Bromides;APIs Intermediate;Adamantane derivatives;Phenol&Thiophenol&Mercaptan
• Mol File: 104224-68-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 137-141
• Boiling Point: 392.044 °C at 760 mmHg
• Flash Point: 190.901 °C
• Appearance: white like or light brown crystalline powder
• Density: 1.442 g/cm³
• Vapor Pressure: 1.04E-06mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.56±0.43(Predicted)
• CAS DataBase Reference: 2-(1-Adamantyl)-4-bromophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-Adamantyl)-4-bromophenol(104224-68-2)
• EPA Substance Registry System: 2-(1-Adamantyl)-4-bromophenol(104224-68-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 104224-68-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

2-(Adamantan-1-yl)-4-bromophenol is an intermediate in the synthesis of Adapalene (A225000), a retinoid selective for retinoic acid receptor (RAR) subtypes β and γ; an antiacne agent.

InChI:InChI=1/C16H19BrO/c17-13-1-2-15(18)14(6-13)16-7-10-3-11(8-16)5-12(4-10)9-16/h1-2,6,10-12,18H,3-5,7-9H2/t10-,11-,12-,16-

Upstream product

• 106-41-2 4-bromo-phenol 
• 768-95-6 1-adamanthanol 
• 22635-62-7 1-acetyloxyadamantane 
• 60-29-7 diethyl ether 

Downstream Products

• 862651-04-5 methyl E-3-[3’-(adamantan-1-yl)-2-chloro-4’-hydroxybiphenyl-4-yl]acrylate 
• 104224-63-7 2-(1-adamantyl)-4-bromoanisole 
• 1036766-54-7 3-(1-adamantyl)-4-methoxybenzene magnesium bromide 
• 221137-01-5 3-(1-adamantyl)-4-benzyloxyphenylboronic acid 
• 943141-83-1 diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate 
• 943141-82-0 diethyl (E)-2-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]ethenylphosphonate 
• 943141-80-8 (3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]-2-oxobut-3-enal 
• 943141-79-5 (3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one 
• 943141-77-3 (E)-2-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]ethenyl-1,3,2-benzodioxaborole 
• 943141-76-2 3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-ethynylbiphenyl 
• 943141-75-1 3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-(2-trimethylsilylethynyl)biphenyl 
• 943141-74-0 3'-(1-adamantyl)-4'-benzyloxy-4-bromo-2-chlorobiphenyl 
• 943141-73-9 3'-(1-adamantyl)-4'-benzyloxy-2-chloro-1,1'-biphenyl-4-ylamine 
• 943141-72-8 3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-nitro-1,1'-biphenyl 

Relevant articles and documents

High-performance intrinsic low-k polymer via the synergistic effect of its three units: Adamantyl, perfluorocyclobutylidene and benzocyclobutene

Perfluorocyclobutylidene (PFCB) polymers have gained much interest as the next generation fluoropolymers due to their low dielectric constant, low surface energy, thermal and thermal oxidative stability and chemical resistance. Herein, we obtained a low-k

A transition metal complex compound, and the compound of the catalyst and a catalyst for large amt. pentavelent carried out in the presence of an olefin multimer manufacturing method

PROBLEM TO BE SOLVED: To provide a transition metal complex compound, an olefin multimerization catalyst having excellent activity and containing the same and a method for producing an olefin multimer carried out in the presence of the catalyst.SOLUTION: This transition metal complex compound is one having a phenoxyimine ligand and this olefin multimerization catalyst contains following component (A) and component (B). (A) is the transition metal compound and (B) is a compound selected from the group consisting of an organic metal compound (B-1), an organic aluminumoxy compound (B-2) and a compound (B-3) forming an ion pair by reacting with the transition metal compound (A).

New synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid and evaluation of the influence of adamantyl group on the DNA binding of a naphthoic retinoid

6[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene), a synthetic aromatic retinoid specific for RARβ and RARγ receptors, has been prepared utilizing a Pd/C-mediated Suzuki coupling between 6-bromo-2-naphthoic acid and 4-methoxyphenyl boronic acid, followed by introduction of an adamantyl group in the position 3 of the formed 6-(4-methoxyphenyl)-2-naphthoic acid. The interaction of 6-(4-methoxyphenyl)-2- naphthoic acid/ethyl ester and the 3-adamantyl analogs with DNA was studied in aqueous solution at physiological conditions by UV-vis spectroscopy. The calculated binding constants Kligand-DNA ranged between 1.1 × 104 M-1 and 1.1 × 105 M-1, the higher values corresponding to those of the adamantylated compounds. Molecular modeling studies have emphasized that the intercalative binding of adapalene and its derivatives to DNA is mainly stabilized by hydrophobic interactions related to the presence of the adamantyl group.