Cas no 1356068-47-7 (3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester)

3-Cyano-2-(diethylamino)pyridine-5-boronic acid pinacol ester is a versatile boronic ester derivative used in cross-coupling reactions, particularly Suzuki-Miyaura couplings, due to its stability and reactivity. The presence of the cyano and diethylamino groups enhances its electronic properties, making it valuable in the synthesis of complex heterocyclic compounds. The pinacol ester moiety improves handling and shelf-life by protecting the boronic acid functionality from protodeboronation. This compound is particularly useful in pharmaceutical and materials science research, where precise functionalization of pyridine scaffolds is required. Its compatibility with a range of reaction conditions and substrates underscores its utility in advanced synthetic applications.
3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester structure
1356068-47-7 structure
Product Name:3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester
CAS No:1356068-47-7
MF:C16H24BN3O2
MW:301.191663742065
MDL:MFCD18434469
CID:1039167
PubChem ID:53217327
Update Time:2025-11-02

3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester Chemical and Physical Properties

Names and Identifiers

    • 2-(Diethylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile
    • 3-Cyano-2-(diethylamino)pyridine-5-boronic acid,pinacol ester
    • A-3444
    • 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester
    • DTXSID80682388
    • MFCD18434469
    • AT14341
    • 1356068-47-7
    • 2-(diethylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile
    • BS-26849
    • AKOS016000993
    • CS-0174436
    • 3-Cyano-2-(diethylamino)pyridine-5-boronic acid pinacol ester
    • MDL: MFCD18434469
    • Inchi: 1S/C16H24BN3O2/c1-7-20(8-2)14-12(10-18)9-13(11-19-14)17-21-15(3,4)16(5,6)22-17/h9,11H,7-8H2,1-6H3
    • InChI Key: RKOAVQWEWYFTRG-UHFFFAOYSA-N
    • SMILES: O1B(C2C=NC(=C(C#N)C=2)N(CC)CC)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 301.19600
  • Monoisotopic Mass: 301.196
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 4
  • Complexity: 426
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 58.4A^2

Experimental Properties

  • PSA: 58.38000
  • LogP: 2.09868

3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester Pricemore >>

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Additional information on 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester

Comprehensive Guide to 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester (CAS No. 1356068-47-7)

3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester (CAS No. 1356068-47-7) is a specialized boronic acid derivative widely used in pharmaceutical research, organic synthesis, and material science. This compound belongs to the class of pyridine boronic esters, which are known for their versatility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic chemistry. Researchers and industries value this compound for its stability, reactivity, and broad applicability in creating complex molecular architectures.

The molecular structure of 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester features a cyano group and a diethylamino substituent on the pyridine ring, enhancing its electronic properties and making it a valuable intermediate in drug discovery. The pinacol ester moiety protects the boronic acid group, improving its shelf life and handling characteristics. This compound is particularly useful in the synthesis of heterocyclic compounds, which are prevalent in many FDA-approved drugs and agrochemicals.

One of the most significant applications of 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester is in the development of kinase inhibitors, a hot topic in cancer research. Kinases play a critical role in cell signaling, and their dysregulation is associated with various cancers. Researchers are actively exploring this compound to design novel small-molecule therapeutics targeting specific kinases. Its boronic acid functionality allows for efficient coupling with aryl halides, enabling the rapid assembly of diverse chemical libraries for high-throughput screening.

In addition to pharmaceuticals, 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester finds applications in material science, particularly in the synthesis of organic electronic materials. The compound’s ability to participate in cross-coupling reactions makes it a valuable building block for creating π-conjugated systems, which are essential for organic light-emitting diodes (OLEDs) and photovoltaic devices. With the growing demand for sustainable energy solutions, this compound is gaining attention in the field of green chemistry and renewable energy technologies.

The market for boronic acid derivatives like 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester is expanding, driven by advancements in drug discovery and organic electronics. Suppliers and manufacturers are increasingly focusing on producing high-purity batches to meet the demands of academic and industrial researchers. Quality control and scalability are critical factors, as impurities can significantly impact the outcomes of sensitive chemical reactions. Companies specializing in fine chemicals are investing in advanced purification techniques to ensure the reliability of this compound for critical applications.

For researchers working with 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester, proper storage and handling are essential to maintain its stability. The compound should be stored in a cool, dry place, preferably under an inert atmosphere, to prevent degradation. Safety data sheets (SDS) provide detailed guidelines for handling, ensuring compliance with laboratory safety standards. As with all chemical reagents, personal protective equipment (PPE) such as gloves and goggles should be used to minimize exposure.

In summary, 3-Cyano-2-(diethylamino)pyridine-5-boronic acid, pinacol ester (CAS No. 1356068-47-7) is a versatile and valuable compound in synthetic chemistry, with significant applications in drug development and material science. Its unique structural features and reactivity make it a preferred choice for researchers exploring new therapeutic agents and advanced materials. As the demand for innovative chemical solutions grows, this compound is poised to play a pivotal role in shaping the future of science and technology.

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