Cas no 1310404-20-6 (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde)

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde is a boronic ester derivative of nicotinaldehyde, serving as a versatile intermediate in organic synthesis and pharmaceutical research. Its key advantages include stability under ambient conditions, facilitated by the tetramethyl dioxaborolane protecting group, which enhances handling and storage. The aldehyde functionality allows for further functionalization via condensation or nucleophilic addition reactions, while the boronate moiety enables Suzuki-Miyaura cross-coupling, a critical transformation in C-C bond formation. This compound is particularly valuable in the synthesis of heterocyclic compounds and bioactive molecules, offering high reactivity and selectivity in metal-catalyzed reactions. Its well-defined structure and purity make it suitable for precise synthetic applications.
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde structure
1310404-20-6 structure
Product Name:4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde
CAS No:1310404-20-6
MF:C12H16BNO3
MW:233.071343421936
CID:1033310
PubChem ID:49760391
Update Time:2025-06-21

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde Chemical and Physical Properties

Names and Identifiers

    • 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde
    • 3-Formylpyridine-4-boronic acid pinacol ester
    • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde
    • AKOS015950159
    • 1310404-20-6
    • CS-0444442
    • DTXSID00678187
    • DS-016638
    • FD10388
    • MDL: MFCD08063101
    • Inchi: 1S/C12H16BNO3/c1-11(2)12(3,4)17-13(16-11)10-5-6-14-7-9(10)8-15/h5-8H,1-4H3
    • InChI Key: QYYPSQCYZQLFIL-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CN=CC=2C=O)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 233.1223235g/mol
  • Monoisotopic Mass: 233.1223235g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 290
  • 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: 48.4?2

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
1515109-250mg
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde
1310404-20-6 98%
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¥8413.00 2024-08-09
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
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Additional information on 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde (CAS No. 1310404-20-6): A Versatile Building Block in Modern Medicinal Chemistry

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde (CAS No. 1310404-20-6) is a significant compound in the field of medicinal chemistry and pharmaceutical research. This compound, often referred to as a boronic ester derivative of nicotinaldehyde, has gained considerable attention due to its unique chemical properties and potential applications in the synthesis of bioactive molecules.

The structure of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde features a boronic ester moiety attached to a nicotinaldehyde backbone. The boronic ester functionality is particularly valuable because it can participate in various chemical reactions, such as Suzuki-Miyaura cross-coupling reactions. These reactions are widely used in the synthesis of complex organic molecules and are essential in the development of new pharmaceuticals.

Recent studies have highlighted the importance of boronic esters in medicinal chemistry. For instance, a 2023 publication in the Journal of Medicinal Chemistry demonstrated the use of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde in the synthesis of novel antitumor agents. The compound served as a key intermediate in the preparation of a series of pyridine-based derivatives with potent anticancer activity against various human cancer cell lines.

The versatility of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde extends beyond its use in antitumor drug development. It has also been employed in the synthesis of compounds with anti-inflammatory and neuroprotective properties. A 2022 study published in Bioorganic & Medicinal Chemistry Letters reported the successful synthesis of a series of nicotinamide derivatives using this compound as a starting material. These derivatives exhibited significant anti-inflammatory activity and were found to be effective in reducing inflammation in animal models.

In addition to its applications in drug discovery and development, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde has been utilized in the field of materials science. Researchers have explored its potential as a building block for the synthesis of functional polymers and materials with unique optical and electronic properties. A 2021 article in Macromolecules described the preparation of conjugated polymers using this compound as a monomer unit. The resulting polymers showed excellent photoluminescence properties and were proposed for use in organic light-emitting diodes (OLEDs).

The synthetic accessibility and functional versatility of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde make it an attractive choice for researchers working on diverse projects. Its ability to undergo efficient cross-coupling reactions allows for the rapid construction of complex molecular architectures. This is particularly beneficial in high-throughput screening (HTS) campaigns where large libraries of compounds are synthesized and tested for biological activity.

In conclusion, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde (CAS No. 1310404-20-6) is a valuable compound with broad applications in medicinal chemistry and materials science. Its unique chemical properties and synthetic flexibility make it an indispensable tool for researchers aiming to develop new bioactive molecules and functional materials. As research continues to advance in these fields, the importance of this compound is likely to grow further.

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