103989-84-0

Basic information

• Product Name: 2-METHYLNAPHTHALENE-1-BORONIC ACID
• Synonyms: 2-METHYLNAPHTHALENE-1-BORONIC ACID;(2-Methylnaphthalen-1-yl)boronic acid;2-Methyl-1-naphthylboronic acid;2-METHYLPHTHALENE-1-BORONIC ACID
• CAS NO: 103989-84-0
• Molecular Formula: C₁₁H₁₁BO₂
• Molecular Weight: 186.01484
• Mol File: 103989-84-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 126℃
• Boiling Point: 393.8°C at 760 mmHg
• Flash Point: 192°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 6.59E-07mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.87±0.30(Predicted)
• CAS DataBase Reference: 2-METHYLNAPHTHALENE-1-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLNAPHTHALENE-1-BORONIC ACID(103989-84-0)
• EPA Substance Registry System: 2-METHYLNAPHTHALENE-1-BORONIC ACID(103989-84-0)

Safety Data

• Hazardous Substances Data: 103989-84-0(Hazardous Substances Data)

Usage

General Description

2-METHYLNAPHTHALENE-1-BORONIC ACID is a chemical compound with the formula C13H11BO2. It is a boronic acid derivative of 2-methylnaphthalene, which is commonly used as a building block in organic synthesis. Boronic acids are known for their ability to form stable complexes with diols and can be used in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds. 2-METHYLNAPHTHALENE-1-BORONIC ACID has potential applications in pharmaceuticals and materials science due to its versatile reactivity and ability to participate in a variety of chemical transformations.

InChI:InChI=1/C11H11BO2/c1-8-6-7-9-4-2-3-5-10(9)11(8)12(13)14/h2-7,13-14H,1H3

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 91-57-6 2-Methylnaphthalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 7439-95-4 magnesium dihydride 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 423158-36-5 4-(2-methyl-naphthalen-1-yl)-2-phenyl-quinazoline 
• 312303-48-3 4,4,5,5-tetramethyl-2-(2-methylnaphthalen-1-yl)-1,3,2-dioxaborolane 
• 814254-89-2 1-(2',6'-dimethylphenyl)-2-methylnaphthalene 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 19634-89-0 (R)-2,2'-dimethyl-1,1'-binaphthyl 
• 32587-64-7 (S)-(+)-2,2'-dimethyl-1,1'-binaphthyl 
• 188-52-3 dibenzo[c,g]phenanthrene 
• 423158-38-7 1-(2-phenyl-quinizolin-4-yl)-naphthalene-2-carbaldehyde 
• 423158-37-6 4-(2-dibromomethyl-naphthalen-1-yl)-2-phenyl-quinazoline 
• 423158-39-8 1-(2-phenyl-quinizolin-4-yl)-naphthalene-2-carbaxylic acid 
• 93870-58-7 2-methyl-1-(2-methylphenyl)naphthalene 

Relevant articles and documents

Efficient synthesis of chiral 1,1′-binaphthalenes by the asymmetric suzuki-miyaura reaction: Dramatic synthetic improvement by simple purification of naphthylboronic acids

Naphthylboronic acids prepared as reported in the literature are contaminated with HCl. A very simple purification prior to their use in Suzuki-Miyaura couplings has been found to be crucial, rendering efficient some reactions that had been reported in th

Synthesis and characterization of ortho-twisted asymmetric anthracene derivatives for blue organic light emitting diodes (OLEDs)

New ortho-twisted asymmetric anthracene derivatives have been synthesized and characterized. The anthracene derivatives show good thermal stability with high glass transition temperatures and a pure blue emission with a narrow full width at half maximum in a film state (λmax = 454 nm with 71 nm for 2-(2-methylnaphtathalene-1-yl)-9,10-di(naphthalene-2-yl)anthracene and λmax = 445 nm with 60 nm for 2-(biphenyl-2-yl)-9,10- di(naphthalene-2-yl)anthracene). A multi-layered device using 2-(2-methylnaphtathalene-1-yl)-9,10-di(naphthalene-2-yl)anthracene as an emitting material exhibits a maximum quantum efficiency of 3.61% (power efficiency of 2.15 lm/W, current efficiency of 3.55 cd/A) and blue Commission Internationale de l'Eclairage chromaticity coordinates (x = 0.15, y = 0.13). A fabricated device using 2-(biphenyl-2-yl)-9,10-di(naphthalene-2-yl)anthracene as an emitting material exhibits a maximum quantum efficiency of 3.7% (power efficiency of 2.11 lm/W, current efficiency of 3.55 cd/A) and a blue Commission Internationale de l'Eclairage chromaticity coordinates (x = 0.15, y = 0.12).

Asymmetric Cyclometalated RuII Polypyridyl-Type Complexes with π-Extended Carbanionic Donor Sets

A series of novel cyclometalated RuII complexes were investigated featuring the tridentate dqp ligand platform (dqp is 2,6-di(quinolin-8-yl)pyridine), in order to utilize the octahedral coordination mode around the Ru center to modulate the electrochemical and photophysical properties. The heteroleptic complexes feature C1 symmetry due to symmetry breaking by the peripheral five- or six-membered carbanionic chelate (phenyl, naphthyl, or anthracenyl units). The chelation mode is controlled by the steric effects and C-H activation selectivity of the ligand, which prompted the development of a general synthesis protocol. The optimized conditions to achieve high overall yields (55-75%) involve NaHCO3 as the base and an simplified purification protocol: i.e., facile chromatographic separation using commercially available amino-functionalized silica applying nonaqueous salt-free conditions to omit the necessity of counterion exchange. The structural, photophysical, and electrochemical properties were studied in depth, and the results were corroborated by density functional theory (DFT) calculations. Steady state and time-resolved spectroscopy revealed red-shifted absorption (up to 750 nm) and weak IR emission (800-1000 nm) combined with prolonged emission lifetimes (up to 20 ns) in comparison to classical tpy-based (tpy is 2,2′:6′,2″-terpyridine) complexes. An enhanced stability was observed by blocking the reactive positions of the carbanionic ligand framework, while the reactive positions may be exploited for further functionalization.

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%).