Cas no 1228431-18-2 (6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile)

6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile is a boronic ester derivative of picolinonitrile, commonly employed as a versatile intermediate in organic synthesis and medicinal chemistry. Its key advantages include stability under ambient conditions and compatibility with Suzuki-Miyaura cross-coupling reactions, enabling efficient C-C bond formation. The electron-withdrawing nitrile group enhances reactivity in nucleophilic substitution and metal-catalyzed transformations. The sterically hindered dioxaborolane moiety improves handling and shelf-life while maintaining high reactivity in coupling reactions. This compound is particularly valuable for constructing complex heterocyclic frameworks, making it useful in pharmaceutical and agrochemical research. Its purity and consistent performance ensure reliable results in synthetic applications.
6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile structure
1228431-18-2 structure
Product Name:6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
CAS No:1228431-18-2
MF:C13H17BN2O2
MW:244.097283124924
CID:2115472
PubChem ID:59363717
Update Time:2025-10-31

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

Names and Identifiers

    • 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
    • 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile
    • DA-35996
    • CS-0176215
    • AT13753
    • MB18736
    • 6-Cyano-2-picoline-4-boronic acid pinacol ester
    • 1228431-18-2
    • 6-Cyano-2-picoline-4-boronicacidpinacolester
    • BS-27321
    • SCHEMBL3387130
    • Inchi: 1S/C13H17BN2O2/c1-9-6-10(7-11(8-15)16-9)14-17-12(2,3)13(4,5)18-14/h6-7H,1-5H3
    • InChI Key: CRVOSNAOGTZJRV-UHFFFAOYSA-N
    • SMILES: O1B(C2C=C(C#N)N=C(C)C=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 244.1383080Da
  • Monoisotopic Mass: 244.1383080Da
  • 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
  • Topological Polar Surface Area: 55.1?2

6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
A2B Chem LLC
AE63820-250mg
6-Cyano-2-picoline-4-boronic acid pinacol ester
1228431-18-2 96%
250mg
$176.00 2024-04-20
A2B Chem LLC
AE63820-1g
6-Cyano-2-picoline-4-boronic acid pinacol ester
1228431-18-2 96%
1g
$391.00 2024-04-20
A2B Chem LLC
AE63820-5g
6-Cyano-2-picoline-4-boronic acid pinacol ester
1228431-18-2 96%
5g
$1316.00 2024-04-20
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
1246885-1g
6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
1228431-18-2 96%
1g
¥12589.00 2024-08-09
1PlusChem
1P009YI4-250mg
6-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
1228431-18-2 96%
250mg
$183.00 2025-02-25
1PlusChem
1P009YI4-5g
6-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
1228431-18-2 96%
5g
$1392.00 2025-02-25
1PlusChem
1P009YI4-1g
6-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
1228431-18-2 96%
1g
$418.00 2025-02-25

Additional information on 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile

Introduction to 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (CAS No. 1228431-18-2)

6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile, with the CAS number 1228431-18-2, is a versatile organic compound that has gained significant attention in the fields of medicinal chemistry and materials science. This compound is characterized by its unique boronic ester functionality and its potential for use in various chemical reactions and biological applications. The structure of this compound includes a picolinonitrile core substituted with a methyl group and a boronic ester moiety, making it a valuable building block for the synthesis of more complex molecules.

The boronic ester functionality in 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile is particularly noteworthy due to its reactivity in Suzuki-Miyaura coupling reactions. These reactions are widely used in organic synthesis to form carbon-carbon bonds between aryl or vinyl halides and boronic acids or esters. The efficiency and selectivity of these reactions make them indispensable in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Recent studies have highlighted the importance of this compound in the development of new therapeutic agents and functional materials.

In the context of medicinal chemistry, 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile has been explored for its potential as a precursor in the synthesis of bioactive compounds. For instance, picolinonitriles are known to exhibit a range of biological activities, including anti-inflammatory and anticancer properties. The introduction of a boronic ester group can enhance the reactivity and functionalization possibilities of these molecules, making them attractive candidates for drug discovery and development.

A recent study published in the Journal of Medicinal Chemistry reported the synthesis and biological evaluation of several picolinonitrile derivatives containing boronic ester groups. The researchers found that these compounds exhibited potent antiproliferative activity against various cancer cell lines. Specifically, 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile was shown to have significant cytotoxic effects on human breast cancer cells (MCF-7) and colon cancer cells (HCT116). These findings suggest that this compound could serve as a lead structure for the development of novel anticancer agents.

Beyond its applications in medicinal chemistry, 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile has also found use in materials science. The boronic ester functionality can be exploited to create functional polymers and coatings with unique properties. For example, researchers at the University of California have developed a series of polymeric materials incorporating boronic ester groups derived from this compound. These materials exhibit enhanced mechanical strength and thermal stability, making them suitable for applications in electronics and aerospace industries.

The synthetic route to 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile typically involves several steps. One common approach is to start with 6-methylpicolinonitrile and introduce the boronic ester group through a series of reactions involving organoboron reagents. The choice of reagents and reaction conditions can significantly impact the yield and purity of the final product. Advanced purification techniques such as column chromatography are often employed to obtain high-purity samples suitable for further applications.

In conclusion, 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (CAS No. 1228431-18-2) is a multifunctional compound with broad applications in medicinal chemistry and materials science. Its unique chemical structure and reactivity make it an important building block for the synthesis of bioactive molecules and functional materials. Ongoing research continues to uncover new possibilities for this compound in various scientific disciplines.

Recommended suppliers
Suzhou Genelee Bio-Technology Co., Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Suzhou Genelee Bio-Technology Co., Ltd.
Wuhan Comings Biotechnology Co., Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Wuhan Comings Biotechnology Co., Ltd.
Hunan Well Medicine Synthesis Technology Co., Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Hunan Well Medicine Synthesis Technology Co., Ltd.
Beyond Pharmaceutical Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Shenzhen Yaoyuan R&D Center Co.,Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Shenzhen Yaoyuan R&D Center Co.,Ltd