Production Method 1

1132669-91-0

913835-76-4

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

209919-30-2

913835-76-4

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

913835-76-4

Reaction Conditions

Reference

A One-pot Dual C - C Bond Forming Cascade Process via Suzuki Coupling and Intramolecular Cyclocondensation: An Access to Functionalized Naphthalenes

Waghmare, Pradip S.; et al, Journal of Organic Chemistry, 2023, 88(19), 13392-13403

Production Method 4

913835-76-4

Reaction Conditions

Reference

Discovery of Clinical Candidate (1R,4r)-4-((R)-2-((S)-6-Fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a Potent and Selective Inhibitor of Indoleamine 2,3-Dioxygenase 1

Kumar, Sanjeev; et al, Journal of Medicinal Chemistry, 2019, 62(14), 6705-6733

Production Method 5

73183-34-3

174265-12-4

913835-76-4

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,

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

• (4-chloro-2-methylphenyl)boronic acid
• 4-Chloro-2-formylphenylboronic Acid Pinacol Ester
• Bis(pinacolato)diborane
• 2-Bromo-5-chlorobenzaldehyde

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

• (4-chloro-2-formylphenyl)boronic acid (913835-76-4)

• 1. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
• 2. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 3. Aluminium complexes with thio-phosphorus ligands: syntheses and characterisations of [Al2(CyPS3)2(CyPHS2)2] and [Al(S2PPh2)3]?
  Robert P. Davies,Maria A. Giménez,Laura Patel,Andrew J. P. White Dalton Trans., 2008, 5705-5707
• 4. An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform?
  Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao You Analyst, 2015,140, 1827-1831
• 5. An antimonate pyrochlore (H1.23Sr0.45SbO3.48) for photocatalytic oxidation of benzene: effective oxygen usage and excellent activity?
  Jing Chen,Yu Shao,Danzhen Li J. Mater. Chem. A, 2017,5, 937-941

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives

Comprehensive Overview of (4-chloro-2-formylphenyl)boronic acid (CAS No. 913835-76-4)

(4-chloro-2-formylphenyl)boronic acid (CAS No. 913835-76-4) is a versatile boronic acid derivative widely used in organic synthesis, pharmaceutical research, and material science. This compound features a unique combination of a formyl group and a boronic acid moiety on a chlorinated benzene ring, making it a valuable intermediate for Suzuki-Miyaura cross-coupling reactions. Its molecular structure enables precise functionalization, which is critical for developing advanced drug candidates and functional materials.

In recent years, the demand for boronic acid-based compounds has surged due to their applications in targeted drug delivery and bioconjugation. Researchers are particularly interested in (4-chloro-2-formylphenyl)boronic acid for its role in synthesizing proteolysis-targeting chimeras (PROTACs), a cutting-edge technology in cancer therapy. The compound's ability to form stable covalent bonds with diols and other nucleophiles also makes it useful in sensor development and diagnostic assays.

The synthesis of (4-chloro-2-formylphenyl)boronic acid typically involves palladium-catalyzed borylation of halogenated aromatic precursors, followed by oxidation. Its high purity and stability under controlled conditions ensure reliable performance in high-throughput screening and combinatorial chemistry. Analytical techniques such as NMR spectroscopy and HPLC are commonly employed to verify its structural integrity.

From an industrial perspective, (4-chloro-2-formylphenyl)boronic acid is gaining traction in the agrochemical sector for designing novel pesticides and herbicides. Its reactivity with heterocycles aligns with the growing need for eco-friendly crop protection solutions. Additionally, the compound's compatibility with green chemistry principles supports sustainable manufacturing practices, a key focus for modern chemical enterprises.

For researchers exploring structure-activity relationships (SAR), (4-chloro-2-formylphenyl)boronic acid serves as a scaffold to optimize bioavailability and binding affinity. Its integration into metal-organic frameworks (MOFs) further expands its utility in gas storage and catalysis. As the scientific community prioritizes precision medicine and smart materials, this compound is poised to play a pivotal role in innovation.

In summary, (4-chloro-2-formylphenyl)boronic acid (CAS No. 913835-76-4) exemplifies the convergence of chemical versatility and practical applicability. Its relevance in drug discovery, material science, and sustainable chemistry underscores its importance in contemporary research. Future studies may uncover additional functionalities, solidifying its status as a cornerstone in advanced synthetic methodologies.

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