Cas no 1217500-86-1 ((2-(Benzyloxy)pyrimidin-5-yl)boronic acid)

(2-(Benzyloxy)pyrimidin-5-yl)boronic acid is a boronic acid derivative featuring a benzyl-protected pyrimidine core, commonly employed as a key intermediate in Suzuki-Miyaura cross-coupling reactions. Its structure combines the reactivity of a boronic acid group with the stability imparted by the benzyloxy substituent, facilitating selective functionalization at the 5-position of the pyrimidine ring. This compound is particularly valuable in pharmaceutical and agrochemical synthesis, where pyrimidine scaffolds are prevalent. The boronic acid moiety ensures compatibility with palladium-catalyzed coupling conditions, while the benzyl group offers straightforward deprotection when needed. High purity and consistent performance make it a reliable choice for constructing complex heterocyclic systems.
(2-(Benzyloxy)pyrimidin-5-yl)boronic acid structure
1217500-86-1 structure
Product Name:(2-(Benzyloxy)pyrimidin-5-yl)boronic acid
CAS No:1217500-86-1
MF:C11H11BN2O3
MW:230.02764248848
MDL:MFCD07375141
CID:835967
PubChem ID:46739560
Update Time:2025-05-20

(2-(Benzyloxy)pyrimidin-5-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • 2-BENZYLOXYPYRIMIDINE-5-BORONIC ACID
    • (2-(Benzyloxy)pyrimidin-5-yl)boronic acid
    • 2-(BENZYLOXY)PYRIMIDINE-5-BORONIC ACID
    • MDL: MFCD07375141
    • Inchi: 1S/C11H11BN2O3/c15-12(16)10-6-13-11(14-7-10)17-8-9-4-2-1-3-5-9/h1-7,15-16H,8H2
    • InChI Key: CYHDQODLSLRGRH-UHFFFAOYSA-N
    • SMILES: O(C1N=CC(B(O)O)=CN=1)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 230.08600
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4

Experimental Properties

  • PSA: 75.47000
  • LogP: -0.26460

(2-(Benzyloxy)pyrimidin-5-yl)boronic acid Pricemore >>

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Additional information on (2-(Benzyloxy)pyrimidin-5-yl)boronic acid

Introduction to (2-(Benzyloxy)pyrimidin-5-yl)boronic Acid (CAS No. 1217500-86-1)

(2-(Benzyloxy)pyrimidin-5-yl)boronic acid is a specialized organic compound with the chemical formula C11H11BNO3. This compound, identified by its CAS number CAS No. 1217500-86-1, has garnered significant attention in the field of pharmaceutical research and chemical synthesis due to its versatile applications. As a boronic acid derivative, it plays a crucial role in various biochemical and medicinal chemistry processes, particularly in the development of innovative therapeutic agents.

The structure of (2-(Benzyloxy)pyrimidin-5-yl)boronic acid consists of a pyrimidine core substituted with a benzyloxy group and a boronic acid moiety. The pyrimidine ring is a common scaffold in many bioactive molecules, often found in nucleoside analogs and kinase inhibitors. The benzyloxy group enhances the solubility and stability of the compound, making it more amenable to further functionalization and derivatization. The boronic acid functionality, on the other hand, is well-known for its ability to participate in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis.

In recent years, (2-(Benzyloxy)pyrimidin-5-yl)boronic acid has been extensively studied for its potential in drug discovery and development. Its unique structural features make it an excellent candidate for designing novel compounds with therapeutic properties. For instance, boronic acids have been explored as inhibitors of enzymes involved in cancer metabolism, such as glycolysis and the pentose phosphate pathway. The pyrimidine moiety, being a part of many pharmacologically active molecules, further enhances its utility in medicinal chemistry.

One of the most notable applications of (2-(Benzyloxy)pyrimidin-5-yl)boronic acid is in the synthesis of targeted therapy agents. Researchers have leveraged its reactivity to develop small-molecule inhibitors that can selectively interact with specific biological targets. These inhibitors have shown promise in preclinical studies for treating various diseases, including cancer and inflammatory disorders. The ability to fine-tune the structure of (2-(Benzyloxy)pyrimidin-5-yl)boronic acid derivatives allows scientists to optimize their binding affinity and selectivity, thereby improving their efficacy as therapeutic agents.

The pharmaceutical industry has also recognized the importance of (2-(Benzyloxy)pyrimidin-5-yl)boronic acid in developing next-generation drugs. Its role in facilitating the construction of complex molecular architectures has made it indispensable in synthetic chemistry. By incorporating this compound into drug candidates, researchers can achieve higher precision and efficiency in their synthetic pathways. This has led to the discovery of several novel compounds that are currently undergoing clinical trials for various therapeutic indications.

Moreover, (2-(Benzyloxy)pyrimidin-5-yl)boronic acid has found applications beyond pharmaceuticals. In materials science, it serves as a key intermediate in the synthesis of advanced polymers and coatings. Its boronic acid group can undergo polymerization reactions, leading to the formation of high-performance materials with unique properties. These materials have potential applications in electronics, aerospace, and other high-tech industries.

The chemical reactivity of (2-(Benzyloxy)pyrimidin-5-yl)boronic acid is another area of significant interest. The boronic acid functionality allows for facile participation in cross-coupling reactions, enabling the construction of complex molecular frameworks with precision. This reactivity has been exploited to develop new synthetic strategies that are more efficient and sustainable compared to traditional methods. Such advancements are crucial for meeting the growing demand for high-quality chemical products while minimizing environmental impact.

In conclusion, (2-(Benzyloxy)pyrimidin-5-yl)boronic acid (CAS No. 1217500-86-1) is a multifaceted compound with broad applications across pharmaceuticals, materials science, and organic synthesis. Its unique structural features and chemical properties make it an invaluable tool for researchers seeking to develop innovative solutions for various challenges. As research continues to uncover new uses for this compound, its significance is expected to grow even further, driving advancements in multiple scientific disciplines.

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