2-(1-Adamantyl)-4-bromophenol

Base Information

• Chemical Name: 2-(1-Adamantyl)-4-bromophenol
• CAS No.: 104224-68-2
• Molecular Formula: C16H19BrO
• Molecular Weight: 307.23
• Hs Code.: 2908199090
• Mol file: 104224-68-2.mol

Synonyms:2-(Adamantan-1-yl)-4-bromophenol;4-Bromo-2-tricyclo[3.3.1.1(3,7)]dec-1-ylphenol;

Chemical Property of 2-(1-Adamantyl)-4-bromophenol

Chemical Property:

• Appearance/Colour: white like or light brown crystalline powder
• Vapor Pressure: 1.04E-06mmHg at 25°C
• Melting Point: 137-141 °C
• Refractive Index: 1.633
• Boiling Point: 392.044 °C at 760 mmHg
• PKA: 9.56±0.43(Predicted)
• Flash Point: 190.901 °C
• PSA: 20.23000
• Density: 1.442 g/cm³
• LogP: 4.62250
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

2-(Adamantan-1-yl)-4-bromophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 2-(1-Adamantyl)-4-bromophenol

There total 5 articles about 2-(1-Adamantyl)-4-bromophenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-bromo-phenol (106-41-2) + 1-adamanthanol (768-95-6) → 2-(1-adamantyl)-4-bromophenol (104224-68-2)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃; for 48h;

DOI:10.1016/j.bioorg.2011.07.003

Reference yield: 83.0%

4-bromo-phenol (106-41-2) + 1-adamanthanol (768-95-6) → 2,6-bis(adamantan-1-yl)-4-bromophenol (352647-04-2) + 2-(1-adamantyl)-4-bromophenol (104224-68-2)

Guidance literature:

With Amberlite 200 (H⁺ form); In 1,2-dichloro-ethane; for 5h; Reflux;

DOI:10.3762/bjoc.8.23

Reference yield:

4-bromo-phenol (106-41-2) + 1-acetyloxyadamantane (22635-62-7) → 2-(1-adamantyl)-4-bromophenol (104224-68-2)

Guidance literature:

With sulfuric acid; In ethanol; n-heptane;

upstream raw materials:

4-bromo-phenol

1-adamanthanol

diethyl ether

1-acetyloxyadamantane

Downstream raw materials:

2-(1-adamantyl)-4-bromo-1-<(tert-butyldimethylsilyl)oxy>benzene

Refernces

• 1、 Haney, Brittney A.,Schrank, Cassandra L.,Wuest, William M.. "Synthesis and biological evaluation of an antibacterial azaborine retinoid isostere". . . Retrieved 2021.
• 2、 Wang, Nan,Wang, Ronghua,Shi, Xia,Zou, Gang. "Ion-exchange-resin-catalyzed adamantylation of phenol derivatives with adamantanols: Developing a clean process for synthesis of 2-(1-adamantyl)-4- bromophenol, A key intermediate of adapalene". experimental part. p. 227 - 233. Retrieved 2012/04/10.