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

description

2-Naphthalene Boronic Acid is an organometallic iridium complex with applications in catalysis and Pharmaceutical manufacturing. It can be also used in the study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols.?

Uses

Different sources of media describe the Uses of 32316-92-0 differently. You can refer to the following data:
1. 2-Naphthaleneboronic acid is a useful research chemical for organic synthesis and other chemical processes.
2. suzuki reaction
3. Used in a study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols. Also employed in a study of a palladium-catalyzed addition of aryl boronic acids to nitriles providing aryl ketones and to aryloxy nitriles providing benzofurans.

Solubility

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

Application

It is used to study the enantioselective rhodium-catalyzed addition reaction of arylboronic acid and 2,2,2-trifluoroacetophenone to generate chiral tertiary trifluoromethanol.? It can also be used to study the palladium-catalyzed addition reaction of arylboronic acid and nitrile to generate aryl ketones, and aromatic adverbial clauses: palladium-catalyzed addition of oxynitrile to benzofuran.

Chemical Properties

yellow crystal powde

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

• 13195-76-1 triisobutyl borate 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 19510-26-0 di-β-naphthyl mercurium 
• 612-55-5 2-iodonaphthalene 
• 580-13-2 2-bromonaphthalene 
• 5419-55-6 Triisopropyl borate 
• 90-14-2 1-Iodonaphthalene 
• 10294-33-4 boron tribromide 
• 7647-01-0 hydrogenchloride 
• 121-43-7 Trimethyl borate 
• 1802-41-1 1-chloromercurionaphthalene 
• 7732-18-5 water 
• 13675-18-8 tetrahydroxydiboron 
• 67-56-1 methanol 

Downstream Products

• 182320-30-5 2-(2-naphthyl)-5-methoxyphenylacetone 
• 42160-93-0 3-(naphthalen-2-yl)cyclohex-2-en-1-one 
• 244615-50-7 4-(naphthalene-2-yl)benzaldehyde 
• 93-08-3 methyl 2-naphthyl ketone 
• 41755-70-8 2-(2-naphthyl)-methylbenzoate 
• 244103-25-1 (E)-3-(2-((naphthalen-3-yl)methyl)phenyl)acrylic acid 
• 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 
• 2039-70-5 (E)-2-styrylnaphthalene 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 612-78-2 2,2'-binaphthalene 

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

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).

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.

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