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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl cyanides

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile (CAS No. 905966-41-8): A Comprehensive Overview

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile (CAS No. 905966-41-8) is a versatile organic compound that has gained significant attention in the fields of medicinal chemistry and materials science. This compound, often referred to as DMPA, is characterized by its unique boronic ester functionality and aromatic structure, making it a valuable building block in various synthetic processes and applications.

The chemical structure of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile consists of a phenylacetonitrile moiety attached to a 5,5-dimethyl-1,3,2-dioxaborinane ring. This combination provides the compound with excellent reactivity and stability, which are crucial for its use in cross-coupling reactions and other synthetic transformations. The boronic ester group is particularly important as it can be readily converted to a boronic acid under mild conditions, facilitating its use in Suzuki-Miyaura coupling reactions.

In recent years, 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile has been extensively studied for its potential applications in the development of new pharmaceuticals. One of the key areas of research involves its use as an intermediate in the synthesis of biologically active compounds. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that this compound can be effectively used to synthesize a series of potent inhibitors of protein-protein interactions (PPIs), which are implicated in various diseases such as cancer and neurodegenerative disorders.

Beyond its pharmaceutical applications, 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile has also found utility in materials science. Its unique electronic properties make it an attractive candidate for the development of organic electronic materials. Research published in the Journal of Materials Chemistry C highlighted the use of this compound in the synthesis of conjugated polymers with enhanced photovoltaic performance. The boronic ester functionality allows for precise control over the polymerization process, leading to materials with tailored properties.

The synthesis of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile typically involves a multi-step process that begins with the formation of the boronic ester group. One common approach is to start with 4-bromophenylacetonitrile and react it with pinacolborane under palladium catalysis to form the desired product. This method has been optimized to achieve high yields and purity levels, making it suitable for large-scale production.

The physical and chemical properties of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile have been well-characterized. It is a white solid at room temperature with a melting point ranging from 70 to 75°C. The compound is soluble in common organic solvents such as dichloromethane and dimethylformamide (DMF), but it is insoluble in water. These properties make it easy to handle and process in various synthetic protocols.

Safety considerations are an important aspect when working with any chemical compound. While 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile is generally considered safe under normal laboratory conditions, proper handling and storage practices should be followed to ensure safety. It is recommended to store the compound in a cool, dry place away from sources of heat or ignition. Additionally, appropriate personal protective equipment (PPE) such as gloves and goggles should be worn when handling this compound.

In conclusion, 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenylacetonitrile (CAS No. 905966-41-8) is a highly versatile compound with a wide range of applications in medicinal chemistry and materials science. Its unique chemical structure and reactivity make it an invaluable tool for researchers and scientists working on the development of new drugs and advanced materials. As research continues to advance in these fields, the importance of this compound is likely to grow even further.

• 7091-41-0(2,4,8,10-Tetraoxa-3,9-diboraspiro[5.5]undecane, 3,9-bis(4-methylphenyl)-)
• 214360-45-9((3-Cyanophenyl)boronic acid, neopentyl glycol ester)
• 396131-82-1(3-Cyanomethylphenylboronic acid, pinacol ester)
• 905966-37-2(1,3,2-Dioxaborinane, 2-[4-(1,1-dimethylethyl)phenyl]-5,5-dimethyl-)
• 138500-86-4(2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile)
• 380481-66-3(5,5-Dimethyl-2-(p-tolyl)-1,3,2-dioxaborinane)
• 5123-05-7(1,3,2-Dioxaborinane, 2-[1,1'-biphenyl]-4-yl-5,5-dimethyl-)
• 5487-93-4(4,4'-Biphenyldiboronic Acid bis(Neopentyl Glycol) Ester)
• 126747-09-9(Benzonitrile, 4-[5-(4-butylphenyl)-1,3,2-dioxaborinan-2-yl]-)
• 214360-44-8(4-Cyanophenylboronic acid, neopentyl glycol ester)