459423-32-6

Basic information

• Product Name: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID
• Synonyms: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID;3-(1-ADAMANTYL)-4-METHOXYPHENYLBORONIC ACID;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid 96%;[4-Methoxy-3-(tricyclo[3.3.1.1(3,7)]dec-1-yl)phenyl]boronic acid;[3-(adaMantan-1-yl)-4-Methoxyphenyl]boronic acid;Boronic acid,B-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-;3-Adamant-1-yl-4-methoxybenzeneboronic acid
• CAS NO: 459423-32-6
• Molecular Formula: C₁₇H₂₃BO₃
• Molecular Weight: 286.17
• Product Categories: blocks;BoronicAcids
• Mol File: 459423-32-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 239-242
• Boiling Point: 475.008 °C at 760 mmHg
• Flash Point: 241.076 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 7.89E-10mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Keep Cold
• PKA: 8.94±0.10(Predicted)
• CAS DataBase Reference: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID(459423-32-6)
• EPA Substance Registry System: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID(459423-32-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 459423-32-6(Hazardous Substances Data)

Usage

Uses

Promotes the ortho hydroxalkylation of phenols by aldehyde. Used as reagent in the proection of thiols as cyclic boronates. This has been utilized to trap cis thiols in oder to prevent over oxidation during dihydroxylation reaction by osmium (4)oxide.

InChI:InChI=1/C17H23BO3/c1-21-16-3-2-14(18(19)20)7-15(16)17-8-11-4-12(9-17)6-13(5-11)10-17/h2-3,7,11-13,19-20H,4-6,8-10H2,1H3

Upstream product

• 121-43-7 Trimethyl borate 
• 104224-63-7 2-(1-adamantyl)-4-bromoanisole 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 106685-41-0 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester 
• 1036766-56-9 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 106685-40-9 adapalene 

Relevant articles and documents

Synthesis of 3-(1-adamantyl)-4-methoxyphenylboric acid

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METHOD FOR PREPARTION OF SUBSTITUTED ADAMANTYLARYMAGNESIUM HALIDES

The present invention concerns fine organic synthesis, particularly the method for preparing of substituted adamantylarylmagnesium halides. The known methods for preparing Grignard's reagent from substituted adamantylarylhalide give very low yeld of the desired product. Substituted adamantylarylhalides are active intermediates that by interacting with various electrophiles provide for a wide range of biologically active compounds. The aim of current invention was to develop a method for preparing substituted adamantylarylmagnesium halides. The aim was attained adding lithium chloride in the Grignard's reagent synthesis by acting on is magnesium metal in dry tetrahydrofuran under argon by substituted adamantylarylhalide. It was demonstrated that adding lithium chloride to adamantylarylhalide within a range from 1:1 to 1:2 provides for stable high yield of the desired end product.

NOVEL THERAPEUTIC AGENTS FOR THE TREATMENT OF CANCER, METABOLIC DISEASES AND SKIN DISORDERS

The present invention is directed to novel compounds according to formula (I) wherein R1, R2, and X are as defined herein. The invention also discloses methods of preparation, pharmaceutical compositions, and methods of disease treatment utilizing pharmaceutical compositions comprising these compounds. The compounds of this invention are novel therapeutic agents for the treatment of cancer, diabetes, metabolic diseases and skin disorders in mammalian subjects. These compounds are also useful modulators of gene expression. They exert their activity by interfering with certain cellular signal transduction cascades. The compounds of the invention are thus also useful for regulating cell differentiation and cell cycle processes that are controlled or regulated by various hormones or cytokines. The invention also discloses pharmaceutical compositions and methods of treatment of disease in mammals.