Cas no 870459-90-8 ((4-(Trifluoromethyl)pyridin-2-yl)boronic acid)

(4-(Trifluoromethyl)pyridin-2-yl)boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex biaryl and heteroaryl structures. The trifluoromethyl group enhances the compound's electron-withdrawing properties, improving reactivity and stability in coupling reactions. This reagent is particularly valuable in pharmaceutical and agrochemical research, where the introduction of a trifluoromethyl-substituted pyridine moiety can modulate biological activity and metabolic stability. Its high purity and consistent performance make it a reliable choice for synthetic applications. Proper handling under inert conditions is recommended to preserve its reactivity, as boronic acids are sensitive to protodeboronation under protic or oxidative conditions.
(4-(Trifluoromethyl)pyridin-2-yl)boronic acid structure
870459-90-8 structure
Product Name:(4-(Trifluoromethyl)pyridin-2-yl)boronic acid
CAS No:870459-90-8
MF:C6H5BF3NO2
MW:190.915611982346
MDL:MFCD08063026
CID:841989
PubChem ID:53398051
Update Time:2025-05-24

(4-(Trifluoromethyl)pyridin-2-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (4-(Trifluoromethyl)pyridin-2-yl)boronic acid
    • 4-(trifluoromethyl)pyridin-2-ylboronic acid
    • 4-(Trifluoromethyl)pyridine-2-boronic acid
    • 4-Trifluoromethylpyridine-2-boronic acid
    • O10099
    • (4-(Trifluoromethyl)pyridin-2-yl)boronicacid
    • Boronic acid, [4-(trifluoromethyl)-2-pyridinyl]-
    • MFCD08063026
    • CS-W018367
    • J-513934
    • KJFNGXQZOZOTHA-UHFFFAOYSA-N
    • 870459-90-8
    • [4-(trifluoromethyl)-2-pyridinyl]boronic acid
    • [4-(trifluoromethyl)pyridin-2-yl]boronic acid
    • AS-49910
    • AKOS006286933
    • DTXSID80694401
    • SCHEMBL14929731
    • EN300-4285582
    • A841922
    • SY046961
    • DB-095760
    • [4-(trifluoromethyl)-2-pyridyl]boronic acid
    • MDL: MFCD08063026
    • Inchi: 1S/C6H5BF3NO2/c8-6(9,10)4-1-2-11-5(3-4)7(12)13/h1-3,12-13H
    • InChI Key: KJFNGXQZOZOTHA-UHFFFAOYSA-N
    • SMILES: FC(C1C=CN=C(B(O)O)C=1)(F)F

Computed Properties

  • Exact Mass: 191.03700
  • Monoisotopic Mass: 191.037
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 176
  • 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: 53.4?2

Experimental Properties

  • Boiling Point: 316.1±52.0℃ at 760 mmHg
  • PSA: 53.35000
  • LogP: -0.21980

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Additional information on (4-(Trifluoromethyl)pyridin-2-yl)boronic acid

Introduction to (4-(Trifluoromethyl)pyridin-2-yl)boronic Acid (CAS No. 870459-90-8)

(4-(Trifluoromethyl)pyridin-2-yl)boronic acid, with the CAS number 870459-90-8, is a specialized organoboron compound that has garnered significant attention in the field of pharmaceutical and materials science due to its unique structural and chemical properties. This compound belongs to the class of boronic acids, which are widely recognized for their utility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis. The presence of a trifluoromethyl group at the 4-position of the pyridine ring introduces additional functionalities that enhance its reactivity and applicability in various synthetic pathways.

The trifluoromethyl group is a key feature that distinguishes this compound from other pyridine-based boronic acids. This substituent not only influences the electronic properties of the molecule but also contributes to its stability and reactivity. Boronic acids are known for their ability to participate in palladium-catalyzed cross-coupling reactions, which are fundamental in the synthesis of complex organic molecules, including pharmaceuticals. The combination of a pyridine ring with a trifluoromethyl group makes (4-(Trifluoromethyl)pyridin-2-yl)boronic acid a valuable intermediate in the development of novel compounds.

In recent years, there has been a growing interest in the use of fluorinated compounds in medicinal chemistry due to their favorable pharmacokinetic properties. The introduction of fluorine atoms into drug molecules can enhance metabolic stability, improve binding affinity, and modulate pharmacological activity. (4-(Trifluoromethyl)pyridin-2-yl)boronic acid leverages these benefits by providing a versatile building block for the synthesis of fluorinated pyridine derivatives. These derivatives have shown promise in various therapeutic areas, including oncology, inflammation, and central nervous system disorders.

The synthesis of (4-(Trifluoromethyl)pyridin-2-yl)boronic acid typically involves the reaction of 2-bromo-4-(trifluoromethyl)pyridine with lithium diisopropylamide followed by quenching with boron tribromide. This method highlights the importance of boronic acids in modern synthetic chemistry. The resulting boronic acid can then be used in cross-coupling reactions to introduce additional functional groups or to construct more complex molecular architectures. The ability to selectively modify specific positions on the pyridine ring makes this compound particularly useful for generating libraries of diverse compounds for high-throughput screening.

One of the most notable applications of (4-(Trifluoromethyl)pyridin-2-yl)boronic acid is in the development of kinase inhibitors. Kinases are enzymes that play critical roles in many cellular processes, and their dysregulation is often associated with diseases such as cancer. By incorporating this boronic acid into drug candidates, researchers can design molecules that specifically target and inhibit aberrant kinase activity. Recent studies have demonstrated the efficacy of such inhibitors in preclinical models, paving the way for new therapeutic strategies.

The use of computational methods has also been instrumental in understanding the reactivity and selectivity of (4-(Trifluoromethyl)pyridin-2-yl)boronic acid. Molecular modeling techniques allow researchers to predict how this compound will behave in different reaction conditions, enabling them to optimize synthetic routes and minimize unwanted side reactions. Additionally, computational studies have helped identify new applications for this compound by highlighting its potential utility in areas such as materials science and catalysis.

In conclusion, (4-(Trifluoromethyl)pyridin-2-yl)boronic acid (CAS No. 870459-90-8) is a multifaceted compound with significant potential in pharmaceutical research and development. Its unique structure, combining a pyridine ring with a trifluoromethyl group, makes it an invaluable tool for synthetic chemists seeking to create novel bioactive molecules. As research continues to uncover new applications for this compound, it is likely to remain a cornerstone of organoboron chemistry for years to come.

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