Cas no 1624715-00-9 (4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile)

4-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile is a boronic ester derivative featuring a pyridine core functionalized with a nitrile group and a tetramethyl dioxaborolane moiety. This compound serves as a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its stable boronate ester group, which enhances handling and storage. The electron-withdrawing nitrile group further modulates reactivity, making it suitable for constructing complex heterocyclic frameworks. Its well-defined structure and compatibility with diverse reaction conditions make it valuable for pharmaceutical and materials science applications. The compound is typically supplied with high purity to ensure consistent performance in synthetic workflows.
4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile structure
1624715-00-9 structure
Product Name:4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile
CAS No:1624715-00-9
MF:C13H17BN2O2
MW:244.097283124924
CID:5465577
PubChem ID:129321214
Update Time:2025-06-09

4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile
    • AT22609
    • Z2049909904
    • 4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile
    • 3-Pyridinecarbonitrile, 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
    • Inchi: 1S/C13H17BN2O2/c1-9-10(6-15)7-16-8-11(9)14-17-12(2,3)13(4,5)18-14/h7-8H,1-5H3
    • InChI Key: UAHADQFHTFLYJY-UHFFFAOYSA-N
    • SMILES: O1B(C2C=NC=C(C#N)C=2C)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 244.1383080 g/mol
  • Monoisotopic Mass: 244.1383080 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 1
  • Complexity: 358
  • 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
  • Molecular Weight: 244.10
  • Topological Polar Surface Area: 55.1

4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile Pricemore >>

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Additional information on 4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile

4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile: A Comprehensive Overview

4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile is a highly specialized organic compound with the CAS Registry Number 1624715-00-9. This compound belongs to the class of boron-containing heterocycles and has garnered significant attention in recent years due to its unique structural features and potential applications in various fields. The molecule consists of a pyridine ring substituted with a methyl group at position 4, a tetramethyl-dioxaborolane moiety at position 5, and a cyano group at position 3. These substituents contribute to its versatile reactivity and functional properties.

The synthesis of 4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile typically involves multi-step organic reactions, including nucleophilic substitutions, coupling reactions, and boron-based cyclizations. Recent advancements in catalytic methodologies have enabled more efficient and selective syntheses of such compounds. For instance, the use of transition metal catalysts like palladium or nickel has facilitated the formation of the dioxaborolane ring under mild conditions. These developments have significantly enhanced the scalability and cost-effectiveness of producing this compound for research and industrial purposes.

One of the most notable applications of 4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile lies in its role as an intermediate in drug discovery programs. The presence of the dioxaborolane group allows for controlled reactivity in cross-coupling reactions, making it an ideal precursor for constructing complex molecular architectures. Recent studies have demonstrated its utility in synthesizing bioactive compounds with potential anti-cancer and anti-inflammatory properties. For example, researchers have employed this compound to develop novel pyridine-based inhibitors targeting specific enzymes involved in disease pathways.

In addition to its pharmaceutical applications, 4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile has also found relevance in materials science. The cyano group at position 3 imparts electron-withdrawing characteristics to the molecule, which can be exploited in designing functional materials such as conductive polymers or sensors. Recent breakthroughs in polymer chemistry have highlighted the potential of this compound as a building block for high-performance electronic materials.

The chemical stability and reactivity of 4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile make it a valuable tool in both academic research and industrial settings. Its ability to undergo selective transformations under various reaction conditions underscores its versatility as a synthetic intermediate. Moreover, the tetramethyl-dioxaborolane moiety provides a unique platform for exploring novel boron-containing materials with unprecedented properties.

From an environmental standpoint, researchers have been investigating the eco-friendly synthesis and disposal methods for 4-Methyl-5-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-3-Carbonitrile to minimize its ecological footprint. Green chemistry approaches, such as using renewable feedstocks and catalytic systems that avoid hazardous byproducts, are being actively pursued. These efforts align with global sustainability goals while ensuring the continued development of this compound for diverse applications.

In conclusion, 4-Methyl

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