Cas no 1207443-48-8 ((4-Ethoxy-2-methoxyphenyl)boronic acid)

(4-Ethoxy-2-methoxyphenyl)boronic acid is a boronic acid derivative commonly employed as a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. Its ethoxy and methoxy substituents enhance its stability and reactivity, making it a valuable reagent for constructing complex aryl-aryl bonds. The compound exhibits good solubility in common organic solvents, facilitating its use in homogeneous catalytic systems. Its well-defined structure ensures high selectivity in coupling reactions, contributing to efficient yields. Additionally, it is often utilized in pharmaceutical and materials science research for the preparation of advanced intermediates. Proper handling under inert conditions is recommended to maintain its stability.
(4-Ethoxy-2-methoxyphenyl)boronic acid structure
1207443-48-8 structure
Product Name:(4-Ethoxy-2-methoxyphenyl)boronic acid
CAS No:1207443-48-8
MF:C9H13BO4
MW:196.008123159409
MDL:MFCD04037217
CID:1089658
Update Time:2025-06-11

(4-Ethoxy-2-methoxyphenyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (4-Ethoxy-2-methoxyphenyl)boronic acid
    • 4-ETHOXY-2-METHOXYPHENYLBORONIC ACID
    • AK141210
    • AB17001
    • AX8281403
    • MDL: MFCD04037217
    • Inchi: 1S/C9H13BO4/c1-3-14-7-4-5-8(10(11)12)9(6-7)13-2/h4-6,11-12H,3H2,1-2H3
    • InChI Key: WMVVZNXFUFZMPF-UHFFFAOYSA-N
    • SMILES: O(CC)C1C=CC(B(O)O)=C(C=1)OC

Computed Properties

  • Exact Mass: 196.09100
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 165
  • Topological Polar Surface Area: 58.9

Experimental Properties

  • PSA: 58.92000
  • LogP: -0.22630

(4-Ethoxy-2-methoxyphenyl)boronic acid Security Information

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Additional information on (4-Ethoxy-2-methoxyphenyl)boronic acid

Introduction to (4-Ethoxy-2-methoxyphenyl)boronic acid (CAS No. 1207443-48-8)

(4-Ethoxy-2-methoxyphenyl)boronic acid (CAS No. 1207443-48-8) is a versatile compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This boronic acid derivative is characterized by its unique functional groups, which include an ethoxy and a methoxy substituent on the phenyl ring, making it a valuable building block for various chemical transformations.

The (4-Ethoxy-2-methoxyphenyl)boronic acid is a white to off-white solid with a molecular formula of C10H13BO3 and a molecular weight of 199.01 g/mol. Its solubility in water is limited, but it dissolves well in polar organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO). These properties make it suitable for use in a wide range of chemical reactions, particularly those involving Suzuki-Miyaura coupling reactions.

In the context of medicinal chemistry, (4-Ethoxy-2-methoxyphenyl)boronic acid has been extensively studied for its potential applications in drug discovery and development. The presence of the boronic acid functional group allows for the formation of stable boronate esters, which can be used to introduce new functionalities into target molecules. This is particularly useful in the synthesis of complex organic molecules with therapeutic potential.

Recent research has highlighted the role of (4-Ethoxy-2-methoxyphenyl)boronic acid in the development of novel pharmaceuticals. For instance, a study published in the *Journal of Medicinal Chemistry* demonstrated that this compound can be used as an intermediate in the synthesis of potent inhibitors of protein-protein interactions (PPIs). These inhibitors have shown promise in treating various diseases, including cancer and neurodegenerative disorders.

In addition to its applications in medicinal chemistry, (4-Ethoxy-2-methoxyphenyl)boronic acid has also found use in materials science. The boronic acid group can form covalent bonds with hydroxyl groups on surfaces, making it useful for surface modification and functionalization. This property has been exploited in the development of advanced materials such as coatings, adhesives, and biomaterials.

The Suzuki-Miyaura coupling reaction is one of the most prominent applications of (4-Ethoxy-2-methoxyphenyl)boronic acid. This palladium-catalyzed cross-coupling reaction is widely used to form carbon-carbon bonds between aryl or vinyl boronic acids and aryl or vinyl halides or triflates. The efficiency and selectivity of this reaction have made it a cornerstone of modern organic synthesis, enabling the rapid construction of complex molecular architectures.

A recent study published in *Organic Letters* reported the use of (4-Ethoxy-2-methoxyphenyl)boronic acid in a highly efficient Suzuki-Miyaura coupling reaction to synthesize a series of substituted biphenyl compounds. These compounds exhibited excellent optical properties and were used as building blocks for organic light-emitting diodes (OLEDs). The success of this study underscores the versatility and importance of (4-Ethoxy-2-methoxyphenyl)boronic acid in both academic research and industrial applications.

Beyond its use in chemical synthesis, (4-Ethoxy-2-methoxyphenyl)boronic acid has also been explored for its potential biological activities. Studies have shown that boronic acids can interact with various biological targets, including enzymes and receptors. For example, a study published in *Bioorganic & Medicinal Chemistry* demonstrated that derivatives of (4-Ethoxy-2-methoxyphenyl)boronic acid exhibited potent inhibitory activity against carbonic anhydrase enzymes, which are implicated in several diseases such as glaucoma and epilepsy.

The safety profile of (4-Ethoxy-2-methoxyphenyl)boronic acid is another important consideration for its use in various applications. While boronic acids are generally considered to be low-toxicity compounds, proper handling and storage precautions should be followed to ensure safety. It is recommended to handle this compound under inert conditions to prevent oxidation and degradation.

In conclusion, (4-Ethoxy-2-meth oxyphenyl)boronic acid (CAS No. 1207443-48-8) is a multifaceted compound with significant potential across multiple scientific disciplines. Its unique chemical properties make it an indispensable tool for researchers working in organic synthesis, medicinal chemistry, materials science, and beyond. As ongoing research continues to uncover new applications and insights into its behavior, (4-Eth oxy-2-meth oxyphen yl)b oron ic ac id is poised to play an increasingly important role in advancing scientific knowledge and technological innovation.

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