Cas no 1072952-48-7 ((2-Bromo-5-methoxypyridin-4-yl)boronic acid)

(2-Bromo-5-methoxypyridin-4-yl)boronic acid is a versatile boronic acid derivative widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions. Its bromo and boronic acid functional groups enable selective modifications of the pyridine ring, facilitating the synthesis of complex heterocyclic compounds. The methoxy substituent enhances electronic properties, making it valuable in pharmaceutical and agrochemical research. This compound exhibits good stability under standard conditions, ensuring reliable handling and storage. Its high purity and consistent reactivity make it a preferred choice for constructing advanced molecular architectures in medicinal chemistry and materials science. Proper handling under inert conditions is recommended to preserve its integrity.
(2-Bromo-5-methoxypyridin-4-yl)boronic acid structure
1072952-48-7 structure
Product Name:(2-Bromo-5-methoxypyridin-4-yl)boronic acid
CAS No:1072952-48-7
MF:C6H7BBrNO3
MW:231.83968091011
MDL:MFCD07781222
CID:841586
PubChem ID:44119383
Update Time:2025-06-29

(2-Bromo-5-methoxypyridin-4-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (2-Bromo-5-methoxypyridin-4-yl)boronic acid
    • 2-Bromo-5-methoxypyridine-4-boronic acid
    • OR3661
    • 1072952-48-7
    • (2-Bromo-5-methoxypyridin-4-yl)boronicacid
    • SCSULHVJKCOJPH-UHFFFAOYSA-N
    • 2-BROMO-5-METHOXYPYRIDIN-4-YLBORONIC ACID
    • AS-48822
    • MFCD07781222
    • CS-0174023
    • 2-Bromo-5-methoxypyridine-4-boronicacid
    • J-001780
    • FD10148
    • SCHEMBL14993687
    • DTXSID20657191
    • AKOS015835738
    • AB42605
    • MDL: MFCD07781222
    • Inchi: 1S/C6H7BBrNO3/c1-12-5-3-9-6(8)2-4(5)7(10)11/h2-3,10-11H,1H3
    • InChI Key: SCSULHVJKCOJPH-UHFFFAOYSA-N
    • SMILES: BrC1=CC(B(O)O)=C(C=N1)OC

Computed Properties

  • Exact Mass: 230.97000
  • Monoisotopic Mass: 230.97
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 149
  • 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: 62.6A^2

Experimental Properties

  • Density: 1.71±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (9 g/l) (25 o C),
  • PSA: 62.58000
  • LogP: -0.46750

(2-Bromo-5-methoxypyridin-4-yl)boronic acid Security Information

  • Hazard Statement: Irritant
  • Hazardous Material Identification: Xi

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Additional information on (2-Bromo-5-methoxypyridin-4-yl)boronic acid

Introduction to (2-Bromo-5-methoxypyridin-4-yl)boronic Acid (CAS No. 1072952-48-7)

(2-Bromo-5-methoxypyridin-4-yl)boronic acid is a significant compound in the realm of organic synthesis and pharmaceutical development, characterized by its unique structural and chemical properties. This boronic acid derivative, identified by the CAS number 1072952-48-7, has garnered considerable attention due to its utility in cross-coupling reactions, particularly Suzuki-Miyaura coupling, which is a cornerstone of modern synthetic chemistry. The presence of both bromine and methoxy substituents on the pyridine ring endows this compound with versatile reactivity, making it a valuable intermediate in the synthesis of complex molecules.

The compound's structure consists of a pyridine core substituted at the 2-position with a bromine atom and at the 5-position with a methoxy group, while the 4-position is functionalized with a boronic acid moiety. This specific arrangement enhances its compatibility with various palladium-catalyzed reactions, enabling the formation of carbon-carbon bonds that are essential for constructing intricate molecular frameworks. In pharmaceutical research, such boronic acid derivatives are frequently employed in the development of novel therapeutic agents, where their ability to undergo efficient coupling reactions under mild conditions is highly advantageous.

Recent advancements in the field have highlighted the role of (2-bromo-5-methoxypyridin-4-yl)boronic acid in the synthesis of bioactive molecules. For instance, studies have demonstrated its effectiveness in generating pyridine-based scaffolds that are prevalent in many drug candidates. The bromine substituent allows for further functionalization via halogen-metal exchange or direct arylation reactions, while the methoxy group can be easily modified through oxidation or demethylation processes. These attributes make it an indispensable tool for medicinal chemists seeking to explore new chemical spaces.

Moreover, the compound's application extends beyond pharmaceuticals into materials science and agrochemicals. In materials science, for example, it serves as a precursor for synthesizing organic semiconductors and ligands used in catalysis. The boronic acid functionality facilitates its integration into polymers and coatings, where it can impart desirable electronic properties. Similarly, in agrochemical research, derivatives of this compound have been investigated for their potential as intermediates in the development of novel pesticides and herbicides.

The synthesis of (2-bromo-5-methoxypyridin-4-yl)boronic acid typically involves multi-step procedures that begin with the selective halogenation and methylation of pyridine derivatives. Advanced synthetic methodologies have been developed to optimize yield and purity, ensuring that the final product meets the stringent requirements of industrial applications. Recent publications have reported novel catalytic systems that enhance the efficiency of these transformations, reducing reaction times and minimizing waste generation.

In conclusion, (2-bromo-5-methoxypyridin-4-yl)boronic acid (CAS No. 1072952-48-7) is a multifaceted compound with broad utility across multiple scientific disciplines. Its role in facilitating cross-coupling reactions has made it an indispensable intermediate in pharmaceutical synthesis, while its adaptability to various functionalization strategies continues to drive innovation in organic chemistry. As research progresses, further applications of this compound are expected to emerge, solidifying its position as a cornerstone of modern synthetic chemistry.

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