269410-19-7

Basic information

• Product Name: 1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one
• Synonyms: 1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one
• CAS NO: 269410-19-7
• Molecular Weight: 322.212
• Mol File: 269410-19-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one(269410-19-7)
• EPA Substance Registry System: 1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one(269410-19-7)

Safety Data

• Hazardous Substances Data: 269410-19-7(Hazardous Substances Data)

Usage

Chemical structure

A complex structure containing a ketone group and a boron-containing ring.

Functional groups

Ketone group, boron-containing ring, and aromatic rings.

Molecular weight

Approximately 322 g/mol.

Appearance

Likely a solid or viscous liquid, depending on the conditions.

Solubility

Soluble in organic solvents such as dichloromethane, tetrahydrofuran, and dimethyl sulfoxide.

Reactivity

Reacts with various nucleophiles and electrophiles due to the presence of the boron-containing ring and the ketone group.

Organic synthesis

Used as a building block for constructing more complex molecules.

Pharmaceutical industry

Employed as a precursor for the development of potential drug candidates.

Chemical research

Valuable tool for studying unique structures and reactivity.

Materials science

Potential applications due to the boron-containing moiety.

Catalysis

The boron-containing ring may have catalytic properties.

Stability

Generally stable under normal laboratory conditions, but sensitive to moisture and oxygen.

Hazards

Potential irritant or toxic if ingested, inhaled, or absorbed through the skin. Proper handling and storage are necessary to minimize risks.

Safety precautions

Use appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat when handling this compound. Work in a well-ventilated area or a fume hood to minimize exposure to vapors.

Upstream product

• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 99-92-3 p-aminobenzophenone 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 1186026-67-4 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)benzene 
• 5731-01-1 4-bromo-4'-acetylbiphenyl 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 5748-38-9 4-acetyl-4'-methylbiphenyl 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1040424-62-1 C₈₆H₉₀O₆ 

Relevant articles and documents

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C?X (heteroatom) and C?C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.