269410-21-1

Basic information

• Product Name: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol
• Synonyms: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol;6-Hydroxynaphthalene-2-boronic acid pinacol ester, 96%;6-(Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol
• CAS NO: 269410-21-1
• Molecular Formula: C₁₆H₁₉BO₃
• Molecular Weight: 270
• Mol File: 269410-21-1.mol

Chemical Properties

• Appearance: White/Solid
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol(269410-21-1)
• EPA Substance Registry System: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol(269410-21-1)

Safety Data

• Hazardous Substances Data: 269410-21-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the formation of new compounds and structures. Its boronic acid nature allows it to undergo reactions such as Suzuki-Miyaura cross-coupling, contributing to the synthesis of complex organic molecules.
Used in Palladium-Catalyzed Coupling Reactions:
In the field of palladium-catalyzed coupling, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol is employed as a key component to form carbon-carbon bonds. Its reactivity in these reactions enables the creation of diverse organic compounds, which are valuable in the development of pharmaceuticals, agrochemicals, and materials science.
Used in Research Applications:
This chemical compound is utilized in research settings to explore its properties and potential applications in various chemical processes. Researchers leverage its reactivity and structural features to investigate new methods of synthesis and to understand its behavior in different reaction conditions.
Used in Industrial Applications:
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol is also employed in industrial applications, particularly in the production of specialty chemicals, pharmaceutical intermediates, and advanced materials. Its versatility in chemical reactions makes it a valuable asset in the synthesis of complex molecules required in various industries.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol is used as a building block for the synthesis of drug candidates. Its ability to form carbon-carbon bonds through palladium-catalyzed coupling reactions is crucial in the development of novel therapeutic agents with specific biological activities.
Used in Material Science:
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol is utilized in material science for the synthesis of advanced materials with unique properties. Its involvement in organic synthesis and coupling reactions allows for the creation of materials with tailored characteristics, such as improved stability, conductivity, or specific interactions with other molecules.

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 173194-95-1 (6-hydroxynaphthalen-2-yl)boronic acid 

Downstream Products

• 1282538-12-8 6-[4-(3-hydroxyprop-1-ynyl)phenyl]naphthalene-2-ol 
• 1426082-99-6 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-1-methoxymethyl-5-pyridin-4-yl-1H-imidazol-4-yl}-naphthalen-2-ol 
• 1227290-21-2 C₂₄H₁₆O 
• 935472-80-3 C₄₃H₂₈N₂O 

Relevant articles and documents

Fluorescent Recognition of Functional Secondary Amines in the Fluorous Phase

In a fluorous solvent (perfluorohexane, FC-72), a perfluoroalkyl-substituted 2-hydroxy-1-naphthaldehyde (1) was found to show greatly enhanced fluorescence when treated with certain functional secondary amines but little fluorescence response was observed with unfunctional amines as well as functional primary and tertiary amines. The study of the reaction of 1 with 2-methylamino ethanol (8) reveals a facile cyclocondensation of the aldehyde group of 1 with this 1,2-amino alcohol to form a 5-membered ring oxazolidine product which turns on the fluorescence. The reaction of 1 with the amino alcohol was found to be more favorable in the fluorous solvent than in a common organic solvent. The use of the fluorous phase-based fluorescence measurement in this work provides a potentially more sensitive as well as selective method in amine sensing.

Fluorous-Phase-Based Chiral Assay with Circular Dichroism Spectroscopy

A highly fluorinated molecular probe made of a salicylaldehyde derivative is designed and synthesized for the detection of chiral amines in the fluorous phase. When treated with various chiral amines in a fluorous solvent (perfluorohexyl ethanol), this probe shows intense CD signals at wavelengths greater than 400 nm, which has been used to determine the enantiomeric composition of chiral amines, amino alcohols, and amino acids. This is the first example of CD recognition of chiral compounds that is conducted in the fluorous phase. The approach could greatly reduce the undesired interference in the direct assay of asymmetric reactions and catalytic processes.

Benzazole derivatives and organic electroluminescent device including the same

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A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

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