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
• Article Data: 26

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 
• 99-02-5 3'-Chloroacetophenone 
• 73183-34-3 bis(pinacol)diborane 
• 1012986-07-0 CF₃C₆H₄SO₂O(C₆H₄COCH₃) 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 98-86-2 acetophenone 
• 1092513-16-0 3-acetylphenyl methanesulfonate 
• 58297-34-0 3-acetylphenyl p-toluenesulfonate 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-71-1 3-Hydroxyacetophenone 
• 586-42-5 3-acetylbenzoic acid 

Downstream Products

• 443777-10-4 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 3112-01-4 3-phenylacetophenone 
• 349-76-8 3'-(trifluoromethyl)acetophenone 
• 82026-75-3 1-(3-(fluoromethyl)phenyl)ethanone 

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.

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.

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.