312303-48-3

Basic information

• Product Name: 2-Methylnaphthalene-1-boronic Acid Pinacol Ester
• Synonyms: 2-Methylnaphthalene-1-boronic Acid Pinacol Ester;4,4,5,5-tetramethyl-2-(2-methylnaphthalen-1-yl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(2-methyl-1-naphthalenyl)-1,3,2-Dioxaborolane
• CAS NO: 312303-48-3
• Molecular Formula: C₁₇H₂₁BO₂
• Molecular Weight: 286.17372
• Mol File: 312303-48-3.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methylnaphthalene-1-boronic Acid Pinacol Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylnaphthalene-1-boronic Acid Pinacol Ester(312303-48-3)
• EPA Substance Registry System: 2-Methylnaphthalene-1-boronic Acid Pinacol Ester(312303-48-3)

Safety Data

• Hazardous Substances Data: 312303-48-3(Hazardous Substances Data)

Usage

General Description

The chemical 2-methylnaphthalene-1-boronic acid pinacol ester is a boronic acid ester derived from 2-methylnaphthalene. It is commonly used in organic synthesis as a reagent for the Suzuki-Miyaura coupling reaction, which is a widely used method for forming carbon-carbon bonds. 2-Methylnaphthalene-1-boronic Acid Pinacol Ester has a pinacol group, which helps to stabilize the boronic acid and improve its reactivity. 2-methylnaphthalene-1-boronic acid pinacol ester is a valuable tool in the toolbox of organic chemists for the formation of complex organic molecules and is widely used in the pharmaceutical and agrochemical industries for the synthesis of biologically active compounds.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 106-93-4 ethylene dibromide 
• 90-14-2 1-Iodonaphthalene 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 38063-26-2 5-hydroxybenzophenanthrene 

Relevant articles and documents

Photoinduced DNA Interstrand Cross-Link Formation by Naphthalene Boronates via a Carbocation

Most photoinduced DNA cross-link formation by a bifunctional aryl derivative is through a bisquinone methide. DNA cross-linking via a bisarylcarbocation remains a less explored area. We designed and synthesized a series of naphthalene boronates that produce DNA interstrand cross-links via a carbocation upon UV irradiation. A free radical was generated from the naphthalene boronates with 350 nm irradiation and further converted to a carbocation by electron transfer. The activation mechanism was determined using the orthogonal traps, 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) and methoxyamine that react with either the free radical or the carbocation but not both. This represents a novel example of photoinduced DNA cross-link formation via carbocations generated from a bisaryl derivative. This work provides information useful for the design of novel photoactivated DNA cross-linking agents.

Synthesis of Phenacene-Helicene Hybrids by Directed Remote Metalation

Polycyclic aromatic hydrocarbons (PAHs) with six and seven rings were synthesized via directed metalation and cross-coupling of chrysenyl N,N-diethyl carboxamides with o-tolyl and methylnaphthalenyl derivatives. In the presence of competing ortho sites, the site selectivity in iodination of chrysenyl amides by directed ortho metalation (DoM) was influenced by the lithium base. The catalyst ligand bite angle was presumably important in the cross-coupling of sterically hindered bulky PAHs. Subsequent directed remote metalation of biaryls under standard conditions and at elevated temperatures afforded various fused six- and seven-ring PAHs, all in good yields and with fluorescent properties.

Mononuclear Copper(I) complexes based on phenanthroline derivatives P^N^N^P tetradentate ligands: Syntheses, crystal structure, photochemical properties

Two novel heteroleptic Cu(I) complexes with the single tetradentate ligands have been designed and synthesized from phenanthroline. The complexes having one copper structure were fully characterized by NMR, ESI-MS and the single-crystal X-ray structures. Their photoelectric chemical properties were investigated by using cyclic voltammetry, UV/vis and fluorescence spectroscopy. Compared with the classic Cu(P^P)(N^N) complexes, this distorted tetrahedral coordination structure of Cu(P^N^N^P) complexes showed a wider excitation wavelength and a red-shifted about 100 nm emission peak, due to the link function between phenanthroline and phosphorus ligands. Moreover, the copper complex B having the naphthyl link groups displayed high red-emissive photoluminescence quantum efficiency (PLQY), which was up to 3.8%.