214360-49-3

Basic information

• Product Name: 3-ACETYLPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 3-ACETYLPHENYLBORONIC ACID, PINACOL ESTER;1-[3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]ETHANONE;1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone ,98%;2-(3-Acetylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-dioxaborolan-2-yl)phenyl]ethanone;1-[3-(tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethan-1-one
• CAS NO: 214360-49-3
• Molecular Formula: C₁₄H₁₉BO₃
• Molecular Weight: 246.11
• Product Categories: Heterocyclic Compounds
• Mol File: 214360-49-3.mol

Chemical Properties

• Melting Point: 51-52°C
• Boiling Point: 362.5 °C at 760 mmHg
• Flash Point: 173.1 °C
• Appearance: /
• Density: 1.04 g/cm³
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-ACETYLPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYLPHENYLBORONIC ACID, PINACOL ESTER(214360-49-3)
• EPA Substance Registry System: 3-ACETYLPHENYLBORONIC ACID, PINACOL ESTER(214360-49-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 214360-49-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-white crystal

InChI:InChI=1/C14H19BO3/c1-10(16)11-7-6-8-12(9-11)15-17-13(2,3)14(4,5)18-15/h6-9H,1-5H3

Upstream product

• 138313-22-1 3-acetylphenyl trifluoromethanesulfonate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 73183-34-3 bis(pinacol)diborane 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 99-02-5 3'-Chloroacetophenone 
• 58297-34-0 3-acetylphenyl p-toluenesulfonate 
• 1092513-16-0 3-acetylphenyl methanesulfonate 
• 1012986-07-0 CF₃C₆H₄SO₂O(C₆H₄COCH₃) 
• 14452-30-3 3'-iodoacetophenone 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 586-42-5 3-acetylbenzoic acid 
• 98-86-2 acetophenone 

Downstream Products

• 1011472-04-0 C₂₃H₂₂N₄O₄ 
• 1011472-13-1 LG₂-81 
• 443777-10-4 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 3112-01-4 3-phenylacetophenone 
• 1246213-54-6 1-methyl-3-{1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1H-pyrrole 
• 121-71-1 3-Hydroxyacetophenone 
• 108-46-3 recorcinol 
• 864754-38-1 (S)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 906067-23-0 1-(3-(2,2,2-trifluoroethyl)phenyl)ethan-1-one 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 1260955-16-5 (S)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine 
• 1260955-17-6 (R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide 
• 887147-35-5 (S)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide 
• 14194-05-9 ethyl 2-(3-acetylphenyl)acetate 

Relevant articles and documents

Highly regioselective Ru(II)-catalyzed [3+2] spiroannulation of 1-aryl-2-naphthols with alkynes via a double directing group strategy

A highly regioselective Ru(II)-catalyzed [3+2] spiroannulation of 1-aryl-2-naphthols with internal alkynes was developed by using a novel double directing group strategy. This method was compatible with many functional groups, thus affording a variety of sterically congested spirocyclic molecules in high yields.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Controllable factors of supported IR complex catalysis for aromatic C?H borylation

We have developed a catalyst in which an Ir complex and organic functionalities are coimmobilized on the silica surface. The catalytic activity for aromatic C?H borylation was significantly affected by (i) the linker length of the Ir?bipyridine complex, (ii) the coimmobilized organic functionality, and (iii) the substituents on the aromatic substrate compounds. The fine-tuned supported catalyst showed higher activity than the homogeneous Ir?bipyridine complex when using a specific substrate such as benzonitrile. We elucidated this property by conducting solid-state NMR, FT-IR, XAFS, and in situ FT-IR analysis.

Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

We report herein the iridium-catalyzed meta-selective C-H borylation of benzamides by using a newly designed 2,2′-bipyridine (bpy) ligand bearing an alkylaluminum biphenoxide moiety. We also demonstrate the iridium-catalyzed C3-selective C-H borylation of pyridine with a 1,10-phenanthroline (Phen) ligand bearing an alkylborane moiety. It is proposed that the Lewis acid-base interaction between the Lewis acid moiety and the aminocarbonyl group or the sp2-hybridized nitrogen atom accelerates the reaction and controls the site-selectivity.

Novel Bruton's tyrosine kinase inhibitor as well as preparation method and application thereof

The invention relates to a reversible novel Bruton's tyrosine kinase inhibitor which comprises a compound of a formula (I) as shown in the specification, and a stereisomer, a aquo-complex, a solvent compound, a pharmaceutically acceptable salt, an eutectic crystal or a predrug of the compound. The invention further relates to a preparation method of the compound and a method and the application ofthe novel compound in inhibiting BTK (Bruton's Tyrosine Kinase) kinase activity and mutant BTK kinase activity.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides

A novel and efficient method for the synthesis of arylboronic acid pinacol esters via a palladium- or iron-catalyzed cross-coupling reaction of aryl fluorides with bis(pinacolato)diboron (B2pin2) in the presence of LiHMDS was developed. The Pd-catalyzed defluoroborylation of fluoroarenes is compatible with a variety of functional groups such as primary and secondary amine, ketone, trifluoromethyl, alkoxy, and boryl. Remarkably, no external ligand is required for enhanced conversion efficiency.

Radical Metal-Free Borylation of Aryl Iodides

A simple metal-free borylation of aryl iodides mediated by a fluoride sp 2 -sp 3 diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.

An electronic transmission material, preparation method and its application

The invention relates to an electron transport material, and a preparation method and application thereof. The electron transport material uses aryl group as the center, wherein one side is connected with a naphthyridine group with electron transport property, and the other side is connected with a group different from naphthyridine with electron transport property, thereby constituting an unsymmetrical structure. The two sides of the aryl group are connected with different groups, thereby destroying the molecular symmetry, further destroying the molecular crystallinity and avoiding the intermolecular aggregation; and thus, the electron transport material has favorable film-forming property. Most groups in the molecule are rigid groups, thereby enhancing the heat stability of the material. Meanwhile, the aryl group is connected with the groups with electron transport property, so that the material has favorable electron transport capacity and hole barrier capacity, and can be used as an electron transport layer for organic electroluminescent devices.