32316-92-0

Basic information

• Product Name: 2-Naphthaleneboronic acid
• Synonyms: AKOS BRN-0020;AKOS BRN-0041;ALPHA-NAPHTHYLBORIC ACID;1-NAPHTHYLENEBORONIC ACID;2-NAPHTHYLBORONIC ACID;2-NAPHTHENEBORONIC ACID;2-NAPHTHALENEYLBORONIC ACID;2-NAPHTHALENEBORONIC ACID
• CAS NO: 32316-92-0
• Molecular Formula: C₁₀H₉BO₂
• Molecular Weight: 171.99
• EINECS: 1312995-182-4
• Product Categories: Industrial/Fine Chemicals;Boron Compounds;blocks;BoronicAcids;Boronic Acid series;Boronic acids;Boronic Acid;Naphthalene;Organoborons;B (Classes of Boron Compounds);OLED materials,pharm chemical,electronic;Boronate Ester;Potassium Trifluoroborate
• Mol File: 32316-92-0.mol
• Article Data: 37

Chemical Properties

• Melting Point: 269-275 °C(lit.)
• Boiling Point: 381.9 °C at 760 mmHg
• Flash Point: 184.8 °C
• Appearance: White to off-white/Crystalline Powder and/or Chunks
• Density: 1.21g/cm³
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: 0-6°C
• PKA: 8.53±0.30(Predicted)
• Water Solubility: Slightly soluble in water
• BRN: 2936449
• CAS DataBase Reference: 2-Naphthaleneboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthaleneboronic acid(32316-92-0)
• EPA Substance Registry System: 2-Naphthaleneboronic acid(32316-92-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 32316-92-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Naphthaleneboronic acid is used as a research chemical for organic synthesis, enabling the development of new compounds and materials.
Used in Suzuki Reaction:
2-Naphthaleneboronic acid is used in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry for the formation of carbon-carbon bonds.
Used in Pharmaceutical Manufacturing:
2-Naphthaleneboronic acid is used in the study of enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones, leading to chiral, tertiary trifluoromethyl alcohols. This application is significant in the synthesis of pharmaceutical compounds.
Used in Chemical Research:
2-Naphthaleneboronic acid is used in the study of palladium-catalyzed addition of aryl boronic acids to nitriles, providing aryl ketones, and to aryloxy nitriles, providing benzofurans. These studies contribute to the advancement of chemical research and the development of new chemical processes.

Solubility

Solubility in water: slightly soluble. Other solubilities: soluble in methanol

InChI:InChI=1/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H

Upstream product

• 19510-26-0 di-β-naphthyl mercurium 
• 612-55-5 2-iodonaphthalene 
• 1802-41-1 1-chloromercurionaphthalene 
• 91-20-3 naphthalene 
• 7732-18-5 water 
• 13675-18-8 tetrahydroxydiboron 
• 580-13-2 2-bromonaphthalene 
• 256652-04-7 4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane 
• 13517-10-7 boron triiodide 
• 67-56-1 methanol 
• 131765-96-3 dicyclohexylamine borane complex 
• 55124-35-1 diisopropylamine borane 
• 121-43-7 Trimethyl borate 
• 150-46-9 triethyl borate 

Downstream Products

• 182320-30-5 2-(2-naphthyl)-5-methoxyphenylacetone 
• 205823-29-6 4-(2-naphthyl)benzoic acid methyl ester 
• 91-20-3 naphthalene 
• 13460-50-9 metaboric acid 
• 274914-47-5 3-methoxycarbonylmethyl-4-naphthalen-2-yl-1-(9-phenyl-9H-fluoren-9-yl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester 
• 373380-73-5 3-(2-naphthalen-2-ylmethylphenyl)acrylic acid methyl ester 
• 288101-23-5 (E)-2-(Benzhydrylidene-amino)-5-(2,4-difluoro-phenyl)-5-naphthalen-2-yl-pent-4-enoic acid methyl ester 
• 50846-93-0 2-chloro-1-(2-naphthyl)ethanone 
• 612-78-2 2,2'-binaphthalene 
• 612-94-2 2-phenylnaphthalene 
• 106359-70-0 4-(naphthalen-2-yl)benzoic acid 

Relevant articles and documents

Regioselectivity in metallation reactions of 2-(2'-naphthyl)pyridine: 1'-versus 3'-reactivity in mercuration and palladation reactions. Crystal structure of chloro(pyridine)3,N>palladium

Regioselectivity is found to vary with the reagent in cyclometallation reactions of 2-(2'-naphthyl)pyridine.Mercuration produces a mixture of 1'- and 3'-naphthyl metallated species with the 1'-substituted material as the major product.Palladation results in clean 3'-naphthyl metallation, as confirmed by the crystal structure of the pyridine derivative chloro(pyridine)3,N>palladium. Keywords: Mercury; Palladium; Cyclometallation; Crystal structure

Synthesis and photophysical processes of 9-bromo-10-naphthalen-2-yl-anthracene

A novel luminescent compound, 9-bromo-10-naphthalen-2-yl-anthracene (BNA) is synthesized by Suzuki Cross-coupling reaction of 9-bromo-anthracene and naphthalene-2-boronic acid. The structure is characterized by 1H NMR, IR and UV-vis spectroscopy. The photophysical processes of 9-bromo-10-naphthalen-2-yl-anthracene have been carefully investigated by UV-vis absorption and fluorescence spectra. The results show that the compound emits blue and blue-violet light. The emission spectra exhibit obvious solvent effect. With the difference in polarity of solvents, The emission spectra is not only slightly blue shift with the increase of the solvent polarity but also change on the intensity of fluorescence at room temperature .The light emitting can be quenched by electron donor, N,N-dimethylaniline (DMA). On adding gradually DMA into the solution of BNA, the emission intensities of fluorescence are gradually decreased. The quenching effect follows the Stern-Volmer equation.

Highly twisted pyrene derivatives for non-doped blue OLEDs

New highly twisted rigid blue light-emitting materials were designed, composed of pyrene with a xylene core unit and either naphthalene or phenyl end units. These blue-emitting materials were synthesized via the Suzuki cross-coupling reaction and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. The optical, electrochemical and thermal properties of the materials were investigated. The non-coplanar structure introduced by highly twisted xylene units provides steric hindrance, resulting in very deep blue emission. The fabricated devices exhibited a maximum external quantum efficiency (EQE) of 3.69% with CIE color coordinates (x, y: 0.15, 0.06).

Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties

A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

BORON DIIODIDE COMPOUND, AND BORONIC ACID, BORONIC ESTER AND THE LIKE OBTAINED THEREFROM, AND PRODUCTION METHOD OF THEM

PROBLEM TO BE SOLVED: To provide a method which enables simple production of a boronic acid, a boronic ester compound or the like suitable for production of various compounds. SOLUTION: The problem is solved by a boron diiodide compound represented by the following general formula (Y). (In the formula (Y), Ar is an n-valent heteroaryl ring, aryl ring having 10 or more carbon atoms, or substituted benzene ring, where at least one hydrogen atom in these rings may be substituted; n is an integer from 1 to 6; and at least one hydrogen atom in the compound represented by the formula (Y) may be substituted with deuterium.) COPYRIGHT: (C)2019,JPO&INPIT

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

Naphtho-fluorene carbazole compound and application thereof

The invention belongs to the field of organic electroluminescence, and in particular relates to a naphtho-fluorene carbazole compound and application thereof. An OLED device manufactured by taking thesynthesized organic compound as a main body light-emitting material can be applied in the fields of AM drive OLED display, PM drive OLED display or OLED illumination. The external quantum efficiency,the power efficiency and the current efficiency of the device are greatly improved, and the service life of the device is obviously prolonged, so that the naphtho-fluorene carbazole compound has thegood market prospect.

CH activation-based transformation of naphthalenes to 3-iodo-2-naphthylboronic acid derivatives for use in iterative coupling synthesis of helical oligo(naphthalene-2,3-diyl)s

Oligo(naphthalene-2,3-diyl)s were synthesized by iterative cross-coupling of 1,8-diaminonaphthalene-modified 3-iodo- 2-naphthylboronic acids prepared from naphthalenes via Ircatalyzed CH borylation, Ru-catalyzed ortho-CH silylation directed by an anthrani