1036766-54-7

Basic information

• Product Name: 3-(1-adamantyl)-4-methoxybenzene magnesium bromide
• Synonyms: 3-(1-adamantyl)-4-methoxybenzene magnesium bromide
• CAS NO: 1036766-54-7
• Molecular Weight: 345.562
• Mol File: 1036766-54-7.mol

Chemical Properties

• CAS DataBase Reference: 3-(1-adamantyl)-4-methoxybenzene magnesium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-adamantyl)-4-methoxybenzene magnesium bromide(1036766-54-7)
• EPA Substance Registry System: 3-(1-adamantyl)-4-methoxybenzene magnesium bromide(1036766-54-7)

Safety Data

• Hazardous Substances Data: 1036766-54-7(Hazardous Substances Data)

Upstream product

• 7439-95-4 magnesium 
• 104224-63-7 2-(1-adamantyl)-4-bromoanisole 
• 106-41-2 4-bromo-phenol 
• 768-95-6 1-adamanthanol 
• 104224-68-2 2-(1-adamantyl)-4-bromophenol 

Downstream Products

• 939822-53-4 3-(1-adamantyl)-4-methoxybenzene zinc chloride 
• 106685-40-9 adapalene 
• 106685-41-0 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester 

Relevant articles and documents

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.

INTERMEDIATES AND PROCESS FOR THE PREPARATION OF AROMATIC DERIVATIVES OF 1-ADAMANTANE

Process for the preparation of aromatic derivatives of 1 -adamantane (tricyclo[3.3.1.1 (3,7)]decane), or an acceptable pharmaceutical salt thereof, based on a hydrolysis reaction of a precursor cyano compound. It also comprises different processes for obtaining the cyano compound. It is especially useful for obtaining Adapalene on an industrial scale in high yield and purity. It also comprises new intermediates useful in said preparation process.