Production Method 1

1207999-25-4

80500-27-2

Reaction Conditions

1.1 Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ,  Water ;  60 min, rt

Reference

Iron trichloride promoted hydrolysis of potassium organotrifluoroborates

Blevins, David W.; et al, Tetrahedron Letters, 2011, 52(49), 6534-6536

Production Method 2

5720-05-8

80500-27-2

Reaction Conditions

Reference

Product subclass 7: hydroxyboranes

Miyaura, N., Science of Synthesis, 2004, 6, 257-300

Production Method 3

182281-36-3

80500-27-2

Reaction Conditions

Reference

Product subclass 7: hydroxyboranes

Miyaura, N., Science of Synthesis, 2004, 6, 257-300

Production Method 4

80500-27-2

Reaction Conditions

Reference

Product subclass 7: hydroxyboranes

Miyaura, N., Science of Synthesis, 2004, 6, 257-300

Production Method 5

624-31-7

331432-85-0

80500-27-2

Reaction Conditions

Reference

Product subclass 7: hydroxyboranes

Miyaura, N., Science of Synthesis, 2004, 6, 257-300

(4-methyl-3-nitrophenyl)boronic acid Raw materials

• 4-Iodotoluene
• Potassium trifluoro(4-methyl-3-nitrophenyl)boranuide
• 4H-4a,9-Methanoazuleno[5,6-d]-1,3,2-dioxaborole, octahydro-5,8,8,9a-tetramethyl-, (3aS,4aR,5R,7aS,9R,9aR)-
• 4-Methylbenzeneboronic Acid
• 1,3,2-Dioxaborinane, 2-(4-methylphenyl)-4,6-diphenyl-, (4R,6R)-rel-

(4-methyl-3-nitrophenyl)boronic acid Preparation Products

• (4-methyl-3-nitrophenyl)boronic acid (80500-27-2)

• 1. Fast synthesis of red Li3BaSrLn3(WO4)8:Eu3+ phosphors for white LEDs under near-UV excitation by a microwave-assisted solid state reaction method and photoluminescence studies
  Bo Wei,Zhenyu Liu,Chen Xie,Shu Yang,Wentao Tang,Aiwei Gu,Wing-Tak Wong,Ka-Leung Wong J. Mater. Chem. C, 2015,3, 12322-12327
• 2. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
• 3. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 4. Excited state potential energy surfaces and their interactions in FeIVO active sites
  Shaun D. Wong,Edward I. Solomon Dalton Trans., 2014,43, 17567-17577
• 5. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990

• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

(4-methyl-3-nitrophenyl)boronic acid: A Versatile Compound in Modern Chemistry and Pharmaceutical Research

(4-methyl-3-nitrophenyl)boronic acid (CAS No. 80500-27-2) is a significant compound in the field of organic chemistry and pharmaceutical research. This boronic acid derivative, characterized by its unique molecular structure, has garnered considerable attention due to its potential applications in various chemical reactions and biological processes. In this article, we will delve into the properties, synthesis, and applications of (4-methyl-3-nitrophenyl)boronic acid, highlighting its importance in contemporary scientific research.

The molecular formula of (4-methyl-3-nitrophenyl)boronic acid is C₈H₉BO₃N, with a molecular weight of approximately 174.06 g/mol. The compound features a benzene ring substituted with a methyl group at the 4-position and a nitro group at the 3-position, along with a boronic acid moiety. This specific arrangement of functional groups imparts unique chemical properties to the molecule, making it an attractive candidate for various synthetic transformations and biological studies.

One of the key applications of (4-methyl-3-nitrophenyl)boronic acid is in Suzuki-Miyaura coupling reactions, a widely used method for forming carbon-carbon bonds. In these reactions, boronic acids react with aryl or vinyl halides in the presence of a palladium catalyst to produce biaryls or styrenes. The presence of the nitro group in (4-methyl-3-nitrophenyl)boronic acid can influence the reactivity and selectivity of the coupling process, making it a valuable reagent for fine-tuning reaction outcomes. Recent studies have demonstrated that the use of (4-methyl-3-nitrophenyl)boronic acid in Suzuki-Miyaura couplings can lead to high yields and excellent regioselectivity, particularly when coupled with electron-deficient aryl halides.

Beyond its role in synthetic chemistry, (4-methyl-3-nitrophenyl)boronic acid has shown promise in pharmaceutical research. The nitro group is known to exhibit redox properties, which can be exploited for developing new therapeutic agents. For instance, nitroaromatic compounds have been investigated for their potential as anti-cancer agents due to their ability to generate reactive oxygen species (ROS) that can induce apoptosis in cancer cells. Recent studies have explored the use of (4-methyl-3-nitrophenyl)boronic acid as a precursor for synthesizing novel anti-cancer drugs. The boronic acid moiety can be readily functionalized to introduce additional pharmacophores, enhancing the compound's biological activity and selectivity.

In addition to its potential as an anti-cancer agent, (4-methyl-3-nitrophenyl)boronic acid has been studied for its use in bioconjugation reactions. Bioconjugation involves linking biomolecules such as proteins, peptides, or nucleic acids to other molecules to create functional hybrids with enhanced properties. The boronic acid group in (4-methyl-3-nitrophenyl)boronic acid can form stable covalent bonds with cis-diol-containing biomolecules under mild conditions, making it an ideal reagent for bioconjugation applications. This property has been leveraged in the development of targeted drug delivery systems and diagnostic tools.

The synthesis of (4-methyl-3-nitrophenyl)boronic acid typically involves several steps. One common approach is to start with 4-methyl-3-nitrotoluene and convert it into the corresponding boronic acid through a series of reactions involving hydroboration and oxidation. The choice of reagents and conditions can significantly impact the yield and purity of the final product. Recent advancements in green chemistry have led to the development of more environmentally friendly methods for synthesizing boronic acids, including microwave-assisted synthesis and catalytic methods that minimize waste generation.

The safety and handling of (4-methyl-3-nitrophenyl)boronic acid are important considerations for researchers working with this compound. While it is not classified as a hazardous material under most regulatory frameworks, proper precautions should be taken to ensure safe handling and storage. The compound should be stored in a cool, dry place away from strong oxidizers and sources of ignition. Personal protective equipment such as gloves and safety goggles should be worn when handling the compound to prevent skin contact and inhalation.

In conclusion, (4-methyl-3-nitrophenyl)boronic acid (CAS No. 80500-27-2) is a versatile compound with significant applications in organic synthesis, pharmaceutical research, and bioconjugation reactions. Its unique molecular structure endows it with valuable chemical properties that make it an essential reagent in modern scientific research. As ongoing studies continue to uncover new uses for this compound, its importance is likely to grow further in the coming years.

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