1036766-56-9

Basic information

• Product Name: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• Synonyms: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• CAS NO: 1036766-56-9
• Molecular Weight: 368.324
• Mol File: 1036766-56-9.mol

Chemical Properties

• CAS DataBase Reference: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(1036766-56-9)
• EPA Substance Registry System: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(1036766-56-9)

Safety Data

• Hazardous Substances Data: 1036766-56-9(Hazardous Substances Data)

Upstream product

• 104224-63-7 2-(1-adamantyl)-4-bromoanisole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 459423-32-6 3-(1-adamantyl)-4-methoxyphenylboronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 106685-41-0 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester 

Relevant articles and documents

Novel adamantyl retinoid-related molecules with POLA1 inhibitory activity

Atypical retinoids (AR) or retinoid-related molecules (RRMs) represent a promising class of antitumor compounds. Among AR, E-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)acrylic acid (adarotene), has been extensively investigated. In the present work we report the results of our efforts to develop new adarotene-related atypical retinoids endowed also with POLA1 inhibitory activity. The effects of the synthesized compounds on cell growth were determined on a panel of human and hematological cancer cell lines. The most promising compounds showed antitumor activity against several tumor histotypes and increased cytotoxic activity against an adarotene-resistant cell line, compared to the parent molecule. The antitumor activity of a selected compound was evaluated on HT-29 human colon carcinoma and human mesothelioma (MM487) xenografts. Particularly significant was the in vivo activity of the compound as a single agent compared to adarotene and cisplatin, against pleural mesothelioma MM487. No reduction of mice body weight was observed, thus suggesting a higher tolerability with respect to the parent compound adarotene.

PROCESS FOR PREPARATION OF 6-[3-(1-ADMANTYL)-4-METHOXYPHENYL]-2-NAPHTOIC ACID.

A process for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid from 2-(1-adamantyl)-4-bromanisolee is disclosed, based on transformation of 2-(1-adamantyl)-4-bromanisole into a Grignard's reagent by using metallic magnesium, anhydrous lithium chloride and dibromoethane followed by transmetallation with borates to 3-(adamantyl)-4-methoxyphenylboronic acid, which is converted into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid esters by Suzuki-Miyaura cross-coupling reaction with alkyl-6-halonaftoates catalyzed by Pd [0] or Pd/phosphine ligands and followed by basic hydrolysis in ethylene glycol or 1,2-propanediol of ester thus obtained into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid.

METHOD FOR PREPARATION OF 6-[3(1-ADAMANTYL) -4-METHOXYPHENYL]-2-NAPHTOIC ACID

A method for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid is disclosed based on “one pot” synthesis approach including a direct synthesis of boronic acid derivative from 2-(1-adamantyl)-4-bromoanisole and cycloboranes with a subsequent Suzuki-Miyaura coupling with 6-halonaphthenoates and basic hydrolysis of the reaction product in ethylene glycol or 1,2-propanediol.