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

Uses

Reactant for:Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactionsSterically hindered Suzuki-Miyaura couplingPalladium-catalyzed cross-coupling reactionsDeboronation homocoupling reactionsCopper-catalyzed N-arylation of imidazolesStereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling

Upstream product

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

Downstream Products

• 39201-98-4 (R_C,R_S)-α<(4-Methylphenyl)sulfinylmethyl>benzenemethanol 
• 75907-52-7 2-methoxy-1-phenylnaphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 1227928-28-0 C₂₂H₁₉NO₃ 

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%).