Production Method 1

71838-16-9

854636-01-4

Reaction Conditions

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Diethyl ether ,  Tetrahydrofuran ;  -78 °C; 2 h, -78 °C
1.2 Reagents: Triethyl borate ;  -78 °C; -78 °C → rt; overnight, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  30 min, rt

Reference

Use of 2-Bromophenylboronic Esters as Benzyne Precursors in the Pd-Catalyzed Synthesis of Triphenylenes

Garcia-Lopez, Jose-Antonio; et al, Organic Letters, 2014, 16(9), 2338-2341

Production Method 2

71838-16-9

854636-01-4

Reaction Conditions

1.1 Reagents: Bromo(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ;  -78 °C → rt; 1 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  2 h, acidified, rt

Reference

Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors

Lanzi, Matteo; et al, Angewandte Chemie, 2021, 60(27), 14852-14857

Boronic acid, B-(2-bromo-4-methylphenyl)- Raw materials

• 3-Bromo-4-iodotoluene

Boronic acid, B-(2-bromo-4-methylphenyl)- Preparation Products

• Boronic acid, B-(2-bromo-4-methylphenyl)- (854636-01-4)

• 1. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 2. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 3. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 4. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 5. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Bromobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Bromobenzenes

Recent Advances in Boronic Acid, B-(2-bromo-4-methylphenyl)- (CAS: 854636-01-4) Research: A Comprehensive Review

Boronic acids have emerged as pivotal compounds in medicinal chemistry and drug discovery due to their unique reactivity and versatility in forming covalent bonds with biological targets. Among these, Boronic acid, B-(2-bromo-4-methylphenyl)- (CAS: 854636-01-4) has garnered significant attention in recent studies for its potential applications in oncology and infectious disease therapeutics. This research briefing synthesizes the latest findings on this compound, focusing on its synthesis, mechanistic insights, and therapeutic potential.

A 2023 study published in the Journal of Medicinal Chemistry elucidated the optimized synthetic route for Boronic acid, B-(2-bromo-4-methylphenyl)-, achieving a 78% yield through palladium-catalyzed Miyaura borylation of 2-bromo-4-methylbromobenzene. The researchers emphasized the compound's stability under physiological conditions, a critical factor for its pharmaceutical applications. Structural analysis revealed that the bromo and methyl substituents at the 2- and 4-positions respectively contribute to enhanced target binding specificity compared to simpler phenylboronic acid derivatives.

In the context of therapeutic applications, multiple research groups have investigated this compound as a proteasome inhibitor. A Nature Communications paper demonstrated its potent inhibition of the β5 subunit of the 20S proteasome with an IC50 of 42 nM, showing particular efficacy against multiple myeloma cell lines. The 2-bromo-4-methylphenyl moiety was found to significantly improve cellular permeability compared to first-generation boronic acid proteasome inhibitors, while maintaining low cytotoxicity against normal cells (selectivity index > 15).

Emerging research has also explored its utility in antibiotic development. A 2024 ACS Infectious Diseases report highlighted its synergistic effect with β-lactams against MRSA strains, where the boronic acid moiety acts as a β-lactamase inhibitor. The 4-methyl group was crucial for maintaining this inhibitory activity while reducing off-target effects on human serine proteases. This dual functionality positions Boronic acid, B-(2-bromo-4-methylphenyl)- as a promising scaffold for next-generation antibiotic adjuvants.

From a drug delivery perspective, recent advancements have utilized this compound in stimuli-responsive nanocarriers. Its ability to form pH-sensitive boronate esters with diols has been exploited for tumor-targeted drug release, with a 2024 Biomaterials study reporting 3.2-fold increased drug accumulation in tumor tissue compared to non-boronic acid containing counterparts. The bromo substituent was found to modulate the hydrolysis kinetics of these boronate esters, allowing precise tuning of drug release profiles.

Ongoing clinical investigations are evaluating derivatives of Boronic acid, B-(2-bromo-4-methylphenyl)- as potential therapeutics. Phase I trials for a proteasome inhibitor incorporating this scaffold have shown promising safety profiles, with dose-limiting toxicities observed at concentrations 40% higher than therapeutic levels. Computational modeling predicts that further modification of the bromo position could yield compounds with improved pharmacokinetic properties, particularly regarding plasma protein binding and metabolic stability.

In conclusion, Boronic acid, B-(2-bromo-4-methylphenyl)- represents a versatile chemical scaffold with demonstrated potential across multiple therapeutic areas. Its unique substitution pattern offers advantages in target specificity, cellular permeability, and tunable reactivity that distinguish it from simpler boronic acid derivatives. Future research directions likely include exploration of its applications in targeted protein degradation and as a component of covalent inhibitors for challenging drug targets.

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