269410-16-4

Basic information

• Product Name: 4-Methoxynaphthalen-1-ylboronic acid pinacol ester
• Synonyms: 4-Methoxynaphthalen-1-ylboronic acid pinacol ester;2-(4-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4-Methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Methoxynaphthalene-1-boronic acid pinacol ester
• CAS NO: 269410-16-4
• Molecular Formula: C17H21BO3
• Molecular Weight: 284.17
• Mol File: 269410-16-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 412.2±28.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Methoxynaphthalen-1-ylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxynaphthalen-1-ylboronic acid pinacol ester(269410-16-4)
• EPA Substance Registry System: 4-Methoxynaphthalen-1-ylboronic acid pinacol ester(269410-16-4)

Safety Data

• Hazardous Substances Data: 269410-16-4(Hazardous Substances Data)

Usage

General Description

4-Methoxynaphthalen-1-ylboronic acid pinacol ester is a chemical compound used in organic synthesis as a boronic acid derivative. It contains a boronic acid functional group, which makes it a versatile reagent for various cross-coupling reactions in the formation of carbon-carbon and carbon-heteroatom bonds. The pinacol ester moiety provides stability and solubility in organic solvents, making it a useful reagent for a wide range of synthetic applications. 4-Methoxynaphthalen-1-ylboronic acid pinacol ester is commonly used in the development of pharmaceuticals, agrochemicals, and materials science, and its unique chemical properties make it an important building block in organic synthesis.

Upstream product

• 5467-58-3 1-bromo-4-methoxynaphthalene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 2216-69-5 1-Methoxynaphthalene 
• 1201594-02-6 4-methoxynaphthalen-1-yl diethylcarbamate 
• 84-85-5 4-methoxynaphth-1-ol 

Relevant articles and documents

Increased Brain Exposure of an Alpha-Synuclein Fibrillization Modulator by Utilization of an Activated Ester Prodrug Strategy

Previous work in our laboratories has identified a series of peptidomimetic 2-pyridone molecules as modulators of alpha-synuclein (α-syn) fibrillization in vitro. As a first step toward developing molecules from this scaffold as positron emission tomography imaging agents, we were interested in evaluating their blood-brain barrier permeability in nonhuman primates (NHP) in vivo. For this purpose, 2-pyridone 12 was prepared and found to accelerate α-syn fibrillization in vitro. Acid 12, and its acetoxymethyl ester analogue 14, were then radiolabeled with 11C (t1/2 = 20.4 min) at high radiochemical purity (>99%) and high specific radioactivity (>37 GBq/μmol). Following intravenous injection of each compound in NHP, a 4-fold higher radioactivity in brain was observed for [11C]14 compared to [11C]12 (0.8 vs 0.2 SUV, respectively). [11C]14 was rapidly eliminated from plasma, with [11C]12 as the major metabolic product observed by radio-HPLC. The presented prodrug approach paves the way for future development of 2-pyridones as imaging biomarkers for in vivo imaging of α-synuclein deposits in brain.

Polysubstituted Pyrimidines as mPGES-1 Inhibitors: Discovery of Potent Inhibitors of PGE2 Production with Strong Anti-inflammatory Effects in Carrageenan-Induced Rat Paw Edema

We report an extensive structure-activity relationship optimization of polysubstituted pyrimidines that led to the discovery of 5-butyl-4-(4-benzyloxyphenyl)-6-phenylpyrimidin-2-amine, and its difluorinated analogue. These compounds are sub-micromolar inh

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.