1400809-84-8 | (3-Fluoro-4'-butyl[1,1'-biphenyl]-4-yl)boronic acid

CAS:1400809-84-8 | (3-Fluoro-4'-butyl[1,1'-biphenyl]-4-yl)boronic acid,Description

“(4’-Butyl-3-fluoro-[1,1’-biphenyl]-4-yl)boronic acid” is a boronic acid derivative. Boronic acids are compounds that contain a boron atom bonded to two hydrogens and one oxygen atom. They are known for their mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared, and generally environmentally benign organoboron reagent.

Synthesis Analysis

The synthesis of boronic acids often involves Suzuki-Miyaura coupling, a widely-applied transition metal catalyzed carbon-carbon bond-forming reaction. This process uses a variety of organoboron reagents, with properties tailored for application under specific coupling conditions.

Chemical Reactions Analysis

Boronic acids, including “(4’-Butyl-3-fluoro-[1,1’-biphenyl]-4-yl)boronic acid”, are often used as reactants in coupling reactions with arenediazonium tetrafluoroborates, iodonium salts, and iodanes. They are also used to make novel biologically active terphenyls.

Scientific Research Applications

Fluorescent Chemosensors

4-4'-Disubstituted biphenyl boronic acids, a category to which (4'-Butyl-3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid belongs, are recognized for their "turn-on" fluorescence properties. They are particularly useful in the detection of carbohydrate triols. The formation of boronate esters in these compounds facilitates photon-induced electron transfer, leading to a Twisted Intramolecular Charge Transfer (TICT) complex. This characteristic is crucial for distinguishing between carbohydrates that bind as diol versus triol units, providing valuable stereochemical information about the carbohydrates (Oesch & Luedtke, 2015).

Synthesis of Organic Materials

Applications in Liquid Crystal Compounds

A compound named 4'-butyl-3-fluoro-biphenyl, which includes (4'-Butyl-3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid, was synthesized and found to be useful in the production of fluorinated biphenyl alkyne monomer liquid crystals. These compounds displayed high optical anisotropy and a wide range of nematic phase, underscoring their potential in the field of liquid crystal technology (Qian Xiu-li, 2010).

Fluorine Substituents Impact

Fluorine atoms in fluoro-substituted boronic acids, like (4'-Butyl-3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid, significantly impact their properties due to their electron-withdrawing character. This characteristic influences their applications in organic synthesis, analytical chemistry, materials’ chemistry, biology, and medicine (Gozdalik et al., 2017).

Applications in Sensing Technologies

Boronic acids, including derivatives like (4'-Butyl-3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid, play a significant role in various sensing technologies. They interact with diols and Lewis bases like fluoride or cyanide anions, leading to their extensive use in sensing applications, ranging from biological labeling to the development of therapeutics (Lacina et al., 2014).

Future Directions

The future directions of research involving “(4’-Butyl-3-fluoro-[1,1’-biphenyl]-4-yl)boronic acid” and other boronic acids could involve further exploration of their use in coupling reactions, the development of new borane reagents, and the synthesis of novel biologically active compounds.

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