Production Method 1

67073-72-7

87199-16-4

Reaction Conditions

1.1 Reagents: Magnesium ,  Lithium chloride Solvents: Tetrahydrofuran ;  rt
1.2 Reagents: Propanoic acid, 2,2-dimethyl-, zinc salt (2:1) ;  15 min, rt
1.3 Reagents: Triisopropyl borate Catalysts: Cuprate(2-), dichloroiodo-, dilithium Solvents: Tetrahydrofuran ;  12 h, rt

Reference

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Fu, Ying ; et al, ChemCatChem, 2018, 10(19), 4253-4257

Production Method 2

850623-42-6

87199-16-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Potassium persulfate ,  Poly(methylhydrosiloxane) Catalysts: Ferrous chloride Solvents: Acetonitrile ,  Water ;  6 h, 80 °C

Reference

Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes

Hu, Penghui; et al, Nature Communications, 2019, 10(1), 1-9

Production Method 3

2246556-65-8

87199-16-4

Reaction Conditions

1.1 Reagents: 1,1,3,3-Tetramethyldisiloxane ,  Oxygen Catalysts: Iron chloride (FeCl3) Solvents: Ethanol ;  12 h, rt

Reference

Iron-catalyzed oxidative C-C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air

Liu, Binbin; et al, Chemical Communications (Cambridge, 2019, 55(33), 4817-4820

Production Method 4

17933-03-8

87199-16-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: 1-Hexadecanaminium, N,N,N-trimethyl-, (PB-7-34-111′1′2)-oxodiperoxy(2-pyridineca… Solvents: Water ;  24 h, 50 °C

Reference

Controlled and Predictably Selective Oxidation of Activated and Unactivated C(sp3)-H Bonds Catalyzed by a Molybdenum-Based Metallomicellar Catalyst in Water

Thiruvengetam, Prabaharan; et al, Journal of Organic Chemistry, 2022, 87(6), 4061-4077

Production Method 5

17933-03-8

87199-16-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Potassium persulfate ,  Poly(methylhydrosiloxane) Catalysts: Ferrous chloride Solvents: Acetonitrile ,  Water ;  6 h, 80 °C

Reference

Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes

Hu, Penghui; et al, Nature Communications, 2019, 10(1), 1-9

Production Method 6

3132-99-8

87199-16-4

Reaction Conditions

Reference

Boron-10 carriers for neutron capture therapy (NCT). A new synthetic method via condensation with aldehydes having boronic moiety

Yamamoto, Yoshinori; et al, Tetrahedron Letters, 1989, 30(51), 7191-4

Production Method 7

87199-16-4

87199-16-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran

Reference

Application of the 'resin-capture-release' methodology to macrocyclization via intramolecular Suzuki-Miyaura coupling

Lobregat, Virginie; et al, Chemical Communications (Cambridge, 2001, (9), 817-818

(3-formylphenyl)boronic acid Raw materials

• 3-Bromobenzaldehyde
• m-Methylphenylboronic Acid
• Potassium (3-Methylphenyl)trifluoroborate
• (3-formylphenyl)boronic acid
• 3-(Prop-2-en-1-yl)phenylboronic acid
• 1-Bromo-3-(dimethoxymethyl)benzene

(3-formylphenyl)boronic acid Preparation Products

• (3-formylphenyl)boronic acid (87199-16-4)

• 1. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 2. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 3. Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids?
  Hui Liu,Deyong Su,Guolin Cheng,Jimin Xu,Xinyan Wang,Yuefei Hu Org. Biomol. Chem., 2010,8, 1899-1904
• 4. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
• 5. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (3-formylphenyl)boronic Acid (CAS No. 87199-16-4)

(3-formylphenyl)boronic acid, with the chemical identifier CAS No. 87199-16-4, is a versatile boronic acid derivative that has garnered significant attention in the field of pharmaceutical and materials science. This compound, characterized by its formyl and boronic acid functional groups, exhibits unique chemical properties that make it a valuable intermediate in organic synthesis and a promising candidate for various applications.

The structure of (3-formylphenyl)boronic acid consists of a phenyl ring substituted with a formyl group at the 3-position and a boronic acid moiety. This arrangement imparts reactivity that is highly useful in cross-coupling reactions, particularly in Suzuki-Miyaura couplings, which are pivotal in the synthesis of complex organic molecules. The boronic acid group can undergo palladium-catalyzed reactions with aryl halides or alkynes, facilitating the formation of carbon-carbon bonds. This property has made (3-formylphenyl)boronic acid an indispensable tool in the development of novel pharmaceuticals and agrochemicals.

In recent years, there has been a surge in research focusing on the applications of boronic acids in drug discovery and development. The ability of boronic acids to form stable complexes with biological molecules has opened up new avenues for therapeutic intervention. For instance, studies have demonstrated the potential of (3-formylphenyl)boronic acid in targeting specific enzymes and receptors involved in disease pathways. Its role in modulating biological processes has been explored in contexts such as cancer therapy, where it has been investigated for its ability to inhibit key enzymes that drive tumor growth.

One of the most compelling aspects of (3-formylphenyl)boronic acid is its utility in materials science. Boronic acids are known for their ability to self-assemble into supramolecular structures, which can be harnessed for the development of advanced materials. Research has shown that (3-formylphenyl)boronic acid can form stable complexes with other organic molecules, leading to the creation of novel polymers and coatings with enhanced properties. These materials have potential applications in electronics, where their unique optical and electronic characteristics could be leveraged to develop next-generation devices.

The synthesis of (3-formylphenyl)boronic acid is another area where significant advancements have been made. Modern synthetic methodologies have enabled the efficient preparation of this compound, making it more accessible for research and industrial applications. Techniques such as lithiation followed by formylation and subsequent borylation have been optimized to yield high-purity (3-formylphenyl)boronic acid. These improvements have not only streamlined the production process but also opened up new possibilities for its use in complex synthetic transformations.

In the realm of pharmaceutical research, (3-formylphenyl)boronic acid has been investigated for its potential as a prodrug or a pharmacophore. Its ability to undergo biotransformation into more active forms within the body makes it an attractive candidate for drug development. Additionally, its role as a precursor in the synthesis of therapeutic agents has been explored, particularly in cases where precise molecular modifications are required to enhance drug efficacy and reduce side effects.

The environmental impact of using (3-formylphenyl)boronic acid as a chemical intermediate has also been a focus of recent studies. Researchers are increasingly interested in developing sustainable synthetic routes that minimize waste and reduce energy consumption. The use of green chemistry principles has led to the development of more eco-friendly methods for synthesizing this compound, aligning with global efforts to promote sustainable practices in chemical manufacturing.

The future prospects for (3-formylphenyl)boronic acid are promising, with ongoing research uncovering new applications and refining existing ones. As our understanding of its chemical properties continues to grow, so too will its role in advancing pharmaceuticals, materials science, and beyond. The compound's unique reactivity and versatility ensure that it will remain a cornerstone of innovation in these fields for years to come.

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