Cas no 871125-90-5 (4-(2-Chlorophenylmethoxy)phenylboronic acid)

4-(2-Chlorophenylmethoxy)phenylboronic acid is a boronic acid derivative featuring a chlorophenylmethoxy substituent, which enhances its utility in cross-coupling reactions such as Suzuki-Miyaura couplings. The presence of the boronic acid group allows for efficient formation of carbon-carbon bonds, while the chlorophenylmethoxy moiety provides steric and electronic modulation, improving selectivity in synthetic applications. This compound is particularly valuable in pharmaceutical and materials science research, where precise functionalization of aromatic systems is required. Its stability under typical reaction conditions and compatibility with various catalysts make it a reliable intermediate for constructing complex molecular architectures. Proper handling under inert conditions is recommended to preserve reactivity.
4-(2-Chlorophenylmethoxy)phenylboronic acid structure
871125-90-5 structure
Product Name:4-(2-Chlorophenylmethoxy)phenylboronic acid
CAS No:871125-90-5
MF:C13H12BClO3
MW:262.496582984924
MDL:MFCD11540655
CID:828014
Update Time:2025-05-24

4-(2-Chlorophenylmethoxy)phenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • (4-((2-Chlorobenzyl)oxy)phenyl)boronic acid
    • [4-[(2-chlorophenyl)methoxy]phenyl]boronic acid
    • 4-(2-ChlorophenylMethoxy)phenylboronic acid
    • 4-(2-Chlorophenylmethoxy)phenylboronic acid
    • MDL: MFCD11540655
    • Inchi: 1S/C13H12BClO3/c15-13-4-2-1-3-10(13)9-18-12-7-5-11(6-8-12)14(16)17/h1-8,16-17H,9H2
    • InChI Key: KJAUPLTZVSARIS-UHFFFAOYSA-N
    • SMILES: ClC1C=CC=CC=1COC1C=CC(B(O)O)=CC=1

Computed Properties

  • Exact Mass: 262.05700
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 4

Experimental Properties

  • PSA: 49.69000
  • LogP: 1.59880

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Additional information on 4-(2-Chlorophenylmethoxy)phenylboronic acid

4-(2-Chlorophenylmethoxy)phenylboronic Acid: A Comprehensive Overview

4-(2-Chlorophenylmethoxy)phenylboronic acid (CAS No. 871125-90-5) is a versatile and highly functionalized compound that has garnered significant attention in the fields of organic synthesis, materials science, and drug discovery. This compound is characterized by its unique structure, which combines a boronic acid group with a chlorophenylmethoxy substituent, making it an ideal building block for various chemical transformations. In this article, we will delve into the properties, applications, and recent advancements associated with this compound.

The molecular structure of 4-(2-Chlorophenylmethoxy)phenylboronic acid consists of a phenyl ring substituted with a boronic acid group at the para position and a chlorophenylmethoxy group at the ortho position. This arrangement imparts the compound with unique electronic and steric properties, rendering it highly reactive in cross-coupling reactions such as Suzuki-Miyaura coupling. Recent studies have highlighted its role in constructing biaryl compounds, which are critical intermediates in the synthesis of pharmaceuticals and advanced materials.

One of the most notable applications of 4-(2-Chlorophenylmethoxy)phenylboronic acid is in the field of medicinal chemistry. Researchers have utilized this compound to develop novel therapeutic agents targeting various diseases, including cancer and neurodegenerative disorders. For instance, a 2023 study published in *Nature Communications* demonstrated that derivatives of this compound exhibit potent anti-tumor activity by modulating key signaling pathways involved in cancer progression.

In addition to its medicinal applications, 4-(2-Chlorophenylmethoxy)phenylboronic acid has found utility in the synthesis of advanced materials. Its ability to undergo controlled polymerization has led to the development of new classes of polymers with tailored electronic properties. A recent breakthrough reported in *Advanced Materials* showcased its use in creating high-performance organic semiconductors for flexible electronics.

The synthesis of 4-(2-Chlorophenylmethoxy)phenylboronic acid typically involves multi-step organic transformations. A common approach involves the coupling of a chlorophenol derivative with a boronic acid precursor under catalytic conditions. Recent advancements in catalysis have enabled more efficient and environmentally friendly syntheses, reducing production costs and minimizing waste generation.

From an analytical standpoint, 4-(2-Chlorophenylmethoxy)phenylboronic acid can be characterized using a variety of techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and X-ray crystallography. These methods provide insights into its molecular structure, purity, and stability under different conditions.

Looking ahead, the potential applications of 4-(2-Chlorophenylmethoxy)phenylboronic acid are vast and continually expanding. Its role as a key intermediate in chemical synthesis underscores its importance in both academic research and industrial applications. As researchers continue to explore its properties and reactivity, new opportunities for innovation are expected to emerge.

In conclusion, 4-(2-Chlorophenylmethoxy)phenylboronic acid (CAS No. 871125-90-5) is a multifaceted compound with significant implications across diverse scientific disciplines. Its unique structure, reactivity, and versatility make it an invaluable tool for advancing modern chemistry and materials science.

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