Production Method 1

1246633-36-2

870238-36-1

Reaction Conditions

1.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran ,  Water ;  20 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, rt

Reference

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

Production Method 2

84459-33-6

870238-36-1

Reaction Conditions

1.1 Reagents: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O) Solvents: Dichloromethane ;  rt; 0.5 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  -78 °C; 1 h, -78 °C
2.2 Reagents: Trimethyl borate ;  1 h, -78 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -78 °C → 5 °C

Reference

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

Production Method 3

148839-33-2

870238-36-1

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Potassium persulfate ,  Poly(methylhydrosiloxane) Catalysts: Ferrous chloride Solvents: Acetonitrile ,  Water ;  5 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 4

870238-36-1

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ;  1 h, -78 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -78 °C → 5 °C

Reference

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

Production Method 5

84459-33-6

73183-34-3

870238-36-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  8 h, 90 °C
2.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran ,  Water ;  20 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, rt

Reference

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

(5-chloro-2-formylphenyl)boronic acid Raw materials

• (5-chloro-2-methylphenyl)boronic acid
• 4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• 2-Bromo-4-chlorobenzaldehyde
• Bis(pinacolato)diborane

(5-chloro-2-formylphenyl)boronic acid Preparation Products

• (5-chloro-2-formylphenyl)boronic acid (870238-36-1)

• 1. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 2. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 3. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
• 4. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 5. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466

The Role of (5-Chloro-2-formylphenyl)Boronic Acid (CAS No. 870238-36-1) in Modern Chemical and Biomedical Research

As a critical intermediate in the synthesis of advanced pharmaceuticals and bioactive molecules, (5-chloro-2-formylphenyl)boronic acid (CAS No. 870238-36-1) has emerged as a focal point in contemporary research due to its unique structural features and reactivity profiles. This compound, characterized by its conjugated aromatic system with a chlorinated ring substituent and a boronic acid moiety, offers exceptional versatility in cross-coupling reactions—a cornerstone of modern medicinal chemistry. Recent advancements in its application have expanded beyond traditional organic synthesis into areas such as targeted drug delivery systems and enzyme inhibition studies, driven by its tunable physicochemical properties.

The 5-chloro substituent imparts electronic perturbations that modulate the compound’s interaction with biological targets, while the formyl group introduces potential for covalent binding or redox-based activation mechanisms. Notably, the boronic acid functional group enables selective Suzuki-Miyaura cross-coupling under mild conditions, facilitating the construction of complex molecular architectures essential for drug candidates targeting oncogenic pathways or neurodegenerative disorders. A 2023 study published in Chemical Science demonstrated its efficacy as a scaffold for synthesizing boron-containing anticancer agents that exhibit selective cytotoxicity toward tumor cells through pH-responsive prodrug activation.

In enzymology research, this compound has been leveraged to develop irreversible inhibitors of serine hydrolases—a family of enzymes implicated in inflammatory diseases—by exploiting the nucleophilic reactivity of the boronic acid group under physiological conditions. A collaborative study between MIT and Genentech highlighted how (5-chloro-2-formylphenyl)boronic acid-based inhibitors achieved sub-nanomolar IC?? values against human neutrophil elastase without compromising metabolic stability, representing a breakthrough in anti-inflammatory therapeutics design.

The formylation site further enables post-synthetic functionalization via aldol condensation or Grignard reactions, allowing researchers to introduce diagnostic imaging tags such as fluorine isotopes for PET imaging applications. A recent Nature Communications paper described its use as a universal linker for conjugating radiohalogens to antibody fragments, achieving tumor-specific targeting with unprecedented precision in preclinical models.

Structural characterization via X-ray crystallography revealed an intramolecular hydrogen bonding network between the boronic oxygen and formyl proton, which stabilizes the molecule’s planar conformation—a property critical for maintaining bioactivity during cellular uptake processes. This structural insight has guided efforts to optimize solubility profiles through esterification strategies reported in a 2024 Angewandte Chemie article that demonstrated up to 9-fold increases in aqueous solubility without compromising catalytic activity.

In material science applications, this compound serves as a building block for self-healing polymers through dynamic covalent chemistry involving reversible boronate ester formation under UV irradiation. Researchers at ETH Zurich recently utilized this property to create stimuli-responsive hydrogels capable of encapsulating therapeutic proteins with controlled release kinetics over 7-day periods—a significant improvement over conventional drug delivery systems.

Safety data from recent toxicological evaluations conducted under OECD guidelines indicate an LD?? exceeding 5 g/kg in rodent models when administered orally or intravenously, underscoring its favorable safety profile compared to traditional organoboron reagents. This attribute positions it advantageously for clinical translation despite requiring standard laboratory precautions during handling.

Ongoing investigations focus on exploiting its photochemical properties—specifically the absorption maxima at ~340 nm—as a photosensitizer for photodynamic therapy (PDT). Preliminary results from Johns Hopkins University show that nanoformulated derivatives induce singlet oxygen generation with quantum yields comparable to established PDT agents like verteporfin while offering superior tissue penetration due to their aromatic backbone.

These multifaceted applications underscore why (5-chloro-2-formylphenyl)boronic acid (CAS No. 870238-36-1) has become indispensable across diverse scientific disciplines—from fundamental organic synthesis to cutting-edge biomedical innovations—while continuously inspiring novel synthetic methodologies and therapeutic strategies.

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