104116-17-8

Basic information

• Product Name: (2-METHOXY-1-NAPHTHYL)BORONIC ACID
• Synonyms: (2-METHOXY-1-NAPHTHYL)BORONIC ACID;2-METHOXY-1-NAPHTHALENEBORONIC ACID;2-Methoxynaphthalene-1-boronic acid;(2-Methoxynaphthalen-1-yl)boronic acid;(2-Methoxy-1-naphthalenyl)boronic acid;1-(2-Methoxynaphthyl)boronic acid;2-Methoxynaphtalene-1-boronic acid
• CAS NO: 104116-17-8
• Molecular Formula: C₁₁H₁₁BO₃
• Molecular Weight: 202.01
• Product Categories: Naphthalene;Organoborons
• Mol File: 104116-17-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 125-130°C
• Boiling Point: 425.2±47.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.53±0.30(Predicted)
• CAS DataBase Reference: (2-METHOXY-1-NAPHTHYL)BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2-METHOXY-1-NAPHTHYL)BORONIC ACID(104116-17-8)
• EPA Substance Registry System: (2-METHOXY-1-NAPHTHYL)BORONIC ACID(104116-17-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 104116-17-8(Hazardous Substances Data)

Usage

Description

(2-METHOXY-1-NAPHTHYL)BORONIC ACID is an organic compound that serves as a versatile reagent in the field of organic synthesis, particularly in cross-coupling reactions. It is characterized by its ability to form stable boronate esters and its compatibility with various reaction conditions, making it a valuable component in the synthesis of complex organic molecules.

Uses

Used in Chemical Synthesis:
(2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a reactant for the design of phosphorus C,P-ligands, which are essential for environmentally benign cross-coupling reactions. These ligands enhance the efficiency and selectivity of the reactions, reducing the environmental impact of the synthetic processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a key intermediate in the synthesis of various drug molecules. Its ability to participate in cross-coupling reactions allows for the creation of complex molecular structures with potential therapeutic applications.
Used in Suzuki-Miyaura Coupling:
(2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a reactant in sterically hindered Suzuki-Miyaura coupling reactions. These reactions are crucial for the formation of carbon-carbon bonds in the synthesis of biologically active compounds and materials with specific properties.
Used in Deboronation Homocoupling Reactions:
In deboration homocoupling reactions, (2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a reactant to form homocoupled products. This application is particularly relevant in the synthesis of symmetrical biaryl compounds, which are important building blocks in various organic molecules and materials.
Used in Copper-Catalyzed N-Arylation:
(2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a reactant in copper-catalyzed N-arylation of imidazoles. This reaction is significant for the synthesis of N-arylated imidazoles, which are valuable intermediates in the preparation of pharmaceuticals and other organic compounds.
Used in Stereoselective Preparation of Biaryl Compounds:
In the stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling, (2-METHOXY-1-NAPHTHYL)BORONIC ACID is used as a reactant. This application is essential for the synthesis of enantiomerically pure biaryl compounds, which are crucial in the development of chiral pharmaceuticals and agrochemicals.

Upstream product

• 121-43-7 Trimethyl borate 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 7732-18-5 water 
• 135-19-3 β-naphthol 
• 5419-55-6 Triisopropyl borate 
• 93-04-9 2-Methoxynaphthalene 
• 688-74-4 boric acid tributyl ester 
• 573-97-7 1-bromo-2-naphthol 

Downstream Products

• 149341-33-3 (R,S)-(±)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline 
• 898257-48-2 (2-hydroxynaphthalen-1-yl)boronic acid 
• 75907-52-7 2-methoxy-1-phenylnaphthalene 

Relevant articles and documents

Pd-catalysed asymmetric SuzukieMiyaura reactions using chiral mono- and bidentate phosphorus ligands

A series of monodentate and bidentate chiral phosphorus based ligands including diphosphites and diphosphonites derived from carbohydrates were tested in the asymmetric Suzuki coupling of aryl halides with 2-substituted 1-naphthylboronic acids. Good activ

An efficient catalyst for the synthesis of ortho-substituted biaryls by the Suzuki cross-coupling: Triphenylphosphine adduct of cyclopalladated ferrocenylimine

The air and moisture stable triphenylphosphine adduct of cyclopalladated ferrocenylimine 2 has been successfully used in palladium-catalyzed Suzuki cross-coupling for the synthesis of ortho-substituted biaryls in air. In the presence of 0.05 mol% of 2 as catalyst and 3 equivalent of CsF as base in dioxane at 100 °C, ortho-substituted biaryls were synthesized with moderate to high yields in the reactions of 2-methoxy-1-naphthylboronic acid with aryl halides, and 14 new ortho-substituted biaryls were obtained and characterized.

Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1- naphthyl)isoquinoline: Two new axially chiral N-O and N-S ligands for asymmetric catalysis

The synthesis and resolution of 1-(2-methoxy-1-naphthyl)isoquinoline and 1-(2-methylthio-1-naphthyl)isoquinoline is reported. These ligands were assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivity up to 68 % was obtained.

Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones

We describe the first atropselective Suzuki-Miyaura cross-coupling of β-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita-Baylis-Hillman reaction is utilized for the Z-selective synthesis of β-keto enol triflates.

Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes

The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yl]phenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%).