1437769-83-9

Basic information

• Product Name: 3-Hydroxynaphthalene-2-boronic acid pinacol ester
• Synonyms: 3-Hydroxynaphthalene-2-boronic acid pinacol ester
• CAS NO: 1437769-83-9
• Molecular Formula: C₁₆H₁₉BO₃
• Molecular Weight: 288.14654
• Mol File: 1437769-83-9.mol

Chemical Properties

• Boiling Point: 414.9±28.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• PKA: 9.46±0.40(Predicted)
• CAS DataBase Reference: 3-Hydroxynaphthalene-2-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxynaphthalene-2-boronic acid pinacol ester(1437769-83-9)
• EPA Substance Registry System: 3-Hydroxynaphthalene-2-boronic acid pinacol ester(1437769-83-9)

Safety Data

• Hazardous Substances Data: 1437769-83-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
3-Hydroxynaphthalene-2-boronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds, which is crucial for the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3-Hydroxynaphthalene-2-boronic acid pinacol ester is used as a key intermediate in the synthesis of various pharmaceuticals, leveraging its reactivity to create complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, 3-Hydroxynaphthalene-2-boronic acid pinacol ester is utilized as a building block for the development of new agrochemicals, contributing to the creation of effective compounds for crop protection and enhancement of agricultural productivity.
Used in Chemical Research:
3-Hydroxynaphthalene-2-boronic acid pinacol ester is also employed in chemical research as a model compound to study the reactivity and mechanisms of boronic acid derivatives in various organic reactions, further expanding the understanding and application of boron chemistry.

Upstream product

• 135-19-3 β-naphthol 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 63389-47-9 2-(diphenylphosphinoxy)naphthyl 
• 30478-88-7 3-bromo-2-naphthol 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Ruthenium-catalyzed regio- And site-selective: Ortho C-H borylation of phenol derivatives

Efficient synthesis of o-borylphenols is achieved through the Ru-catalyzed regio- and site-selective sp2 C-H borylation of aryl diphenylphosphinites followed by removal of the phosphorus directing group. A successful application to aryl phosphites enables practical one-pot borylation of phenols, demonstrating high synthetic utility of this protocol.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT COMPRISING THE SAME, AND ELECTRONIC DEVICE THEREOF

Disclosed are a compound represented by chemical formula 1; an organic electronic element including a first electrode, a second electrode, and an organic layer disposed between the first and second electrodes; and an electronic device including the same. By including the compound represented by chemical formula 1 in the organic layer, the driving voltage of the organic electronic element can be reduced, and the luminance efficiency and the life thereof can be improved.COPYRIGHT KIPO 2017

Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions

A strategy for affecting ortho versus meta/para selectivity in Ir-catalyzed C-H borylations (CHBs) of phenols is described. From selectivity observations with ArylOBpin (pin = pinacolate), it is hypothesized that an electrostatic interaction between the partial negatively charged OBpin group and the partial positively charged bipyridine ligand of the catalyst favors ortho selectivity. Experimental and computational studies designed to test this hypothesis support it. From further computational work a second generation, in silico designed catalyst emerged, where replacing Bpin with Beg (eg = ethylene glycolate) was predicted to significantly improve ortho selectivity. Experimentally, reactions employing B2eg2 gave ortho selectivities > 99%. Adding triethylamine significantly improved conversions. This ligand-substrate electrostatic interaction provides a unique control element for selective C-H functionalization.

Generation of arynes via ate complexes of arylboronic esters with an ortho-leaving group

An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert- or sec-butyllithium. Monitoring the reaction by 11B NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.