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

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

Uses

Used in Pharmaceutical Development:
4-Methoxynaphthalen-1-ylboronic acid pinacol ester is used as a synthetic intermediate for the creation of various pharmaceutical compounds. Its ability to form carbon-carbon and carbon-heteroatom bonds facilitates the synthesis of complex organic molecules with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-Methoxynaphthalen-1-ylboronic acid pinacol ester is used as a key reagent in the synthesis of pesticides and other agrochemicals. Its versatility in cross-coupling reactions allows for the development of new compounds with improved efficacy and selectivity in crop protection.
Used in Materials Science:
4-Methoxynaphthalen-1-ylboronic acid pinacol ester is utilized as a building block in the synthesis of advanced materials with specific properties. Its role in forming carbon-carbon and carbon-heteroatom bonds contributes to the development of materials with tailored characteristics for applications in various industries, such as electronics, energy, and nanotechnology.
Used in Organic Synthesis Research:
As a versatile reagent, 4-Methoxynaphthalen-1-ylboronic acid pinacol ester is used in academic and industrial research settings to explore new synthetic pathways and develop innovative cross-coupling reactions. Its unique properties make it an essential tool for expanding the scope of organic synthesis and discovering new chemical compounds with potential applications across various fields.

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.

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxy-naphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2–0.4, reaching in some cases values as high as 0.5–0.6. Laser-flash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signal.

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

Stealth fast photoswitching of negative photochromic naphthalene-bridged phenoxyl-imidazolyl radical complexes

Naphthalene-bridged phenoxyl-imidazolyl radical complex (Np-PIC) is a novel fast switchable negative photochromic compound, which shows the thermal back reaction in the millisecond time scale. Upon UV light irradiation, Np-PIC shows the hypochromic effect

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.

Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds

Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C-O and C-N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C-H functionalization using 2-pyridyloxy as the directing group.

TYPE IV SECRETION SYSTEM INHIBITORS

Described are compounds, compositions, and methods for treating or preventing conditions or disorders caused by or associated with bacterial type IV secretion systems.

Borylated arylisoquinolines: Photophysical properties and switching behavior of promising tunable fluorophores

A series of nine borylated arylisoquinolines has been prepared with systematic variation in their electronic properties and their photophysical properties were investigated. The color of their fluorescence can be finely tuned by changing the properties of the aryl moiety, which is involved in internal-charge-transfer processes. For example, methoxy-substituted compound 5 showed an intense green emission, whereas dimethylamino-substituted compound 6 showed an orange-red emission. These new fluorophores were tested for their potential as molecular switches with external ionic stimuli, such as protons and fluoride ions. On the one hand, protonation of the isoquinoline moiety led to fluorescence enhancement for compounds that showed weak charge transfer and fluorescence quenching for compounds that showed strong charge transfer. On the other hand, the formation of ate complexes with fluoride led to strong fluorescence quenching in all of the investigated cases. 2 in 1: Borylated arylisoquinolines are tunable and quite versatile molecular entities for the fluorescence sensing of protons and fluoride ions (see figure). A series of compounds with different electronic properties was investigated for various switching modes (quenching, enhancement, ratiometric response). Copyright

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.

Substituted imidazol-pyridazine derivatives

The present invention relates to compounds of formula wherein A is an unsubstituted or substituted cyclic group; and R is hydrogen or lower alkyl; or a pharmaceutically acceptable acid addition salt thereof. These compounds are NMDA NR-2B receptor subtype specific blockers and are useful in the treatment of neurodegeneration, depression and pain.