Cas no 745784-12-7 (Quinolin-2-ylboronic acid)

Quinolin-2-ylboronic acid is a boronic acid derivative featuring a quinoline scaffold, commonly employed as a versatile intermediate in organic synthesis and cross-coupling reactions, particularly Suzuki-Miyaura couplings. Its stable boronic acid group enables efficient formation of carbon-carbon bonds, making it valuable in pharmaceutical and materials science research. The quinoline moiety enhances its utility in constructing complex heterocyclic systems. This compound exhibits good solubility in common organic solvents, facilitating handling in synthetic applications. It is often utilized in the preparation of bioactive molecules, catalysts, and functional materials. Proper storage under inert conditions is recommended to maintain stability and reactivity.
Quinolin-2-ylboronic acid structure
Quinolin-2-ylboronic acid structure
Product Name:Quinolin-2-ylboronic acid
CAS No:745784-12-7
MF:C9H8BNO2
MW:172.976322174072
MDL:MFCD03095375
CID:68736
PubChem ID:22173501
Update Time:2025-06-25

Quinolin-2-ylboronic acid Chemical and Physical Properties

Names and Identifiers

    • Quinolin-2-ylboronic acid
    • Quinoline-2-boronic acid
    • quinolin-2-yl-2-boronic acid
    • 2-Quinoline boronic acid
    • 2-Quinolinylboronic acid
    • 745784-12-7
    • quinolineboronic
    • FT-0603702
    • SCHEMBL27924
    • MFCD03095375
    • 2-quinolinyl-boronic acid
    • A838164
    • AC-22330
    • (quinolin-2-yl)boronic acid
    • J-510323
    • CS-0175272
    • AKOS005259699
    • GS-6154
    • DWHCQRBWSBKHMI-UHFFFAOYSA-N
    • 2-Quinolinylboronic acid;Quinoline-2-boronic acid
    • EN300-212536
    • AMY10983
    • AB13731
    • quinoline boronic acid
    • Quinolin-2-ylboronicacid
    • A9548
    • DTXSID70623225
    • 4-(4-CARBOXYPHENYL)PIPERIDINEHCL
    • F16122
    • DB-032269
    • 800-408-6
    • MDL: MFCD03095375
    • Inchi: 1S/C9H8BNO2/c12-10(13)9-6-5-7-3-1-2-4-8(7)11-9/h1-6,12-13H
    • InChI Key: DWHCQRBWSBKHMI-UHFFFAOYSA-N
    • SMILES: OB(C1=CC=C2C=CC=CC2=N1)O

Computed Properties

  • Exact Mass: 173.06500
  • Monoisotopic Mass: 173.065
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 177
  • 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: 53.4A^2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.3±0.1 g/cm3
  • Melting Point: >300 C
  • Boiling Point: 400.3±37.0 °C at 760 mmHg
  • Flash Point: 195.9±26.5 °C
  • Refractive Index: 1.645
  • PSA: 53.35000
  • LogP: -0.08540
  • Vapor Pressure: 0.0±1.0 mmHg at 25°C

Quinolin-2-ylboronic acid Security Information

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Additional information on Quinolin-2-ylboronic acid

Quinolin-2-ylboronic Acid: A Comprehensive Overview

Quinolin-2-ylboronic acid (CAS No. 745784-12-7) is a versatile compound that has garnered significant attention in the fields of organic synthesis, materials science, and drug discovery. This compound, characterized by its quinoline skeleton with a boronic acid group at the 2-position, serves as a valuable building block in various chemical reactions. Its unique structure enables it to participate in cross-coupling reactions, making it an essential intermediate in the synthesis of complex molecules.

The synthesis of Quinolin-2-ylboronic acid has been optimized over the years, with researchers exploring various methodologies to enhance yield and efficiency. Recent studies have focused on catalytic systems that facilitate the formation of this compound from quinoline derivatives. For instance, the use of palladium catalysts in Suzuki-Miyaura coupling reactions has proven to be highly effective for incorporating the boronic acid group into the quinoline framework. These advancements have not only streamlined the production process but also opened new avenues for its application in medicinal chemistry.

In terms of applications, Quinolin-2-ylboronic acid has found extensive use in the construction of heterocyclic compounds, which are crucial in drug design. Its ability to undergo cross-coupling reactions with aryl halides has made it a key player in the synthesis of biologically active molecules. Recent research highlights its role in developing potential anticancer agents, where the quinoline moiety contributes to bioactivity while the boronic acid group facilitates further functionalization.

Moreover, Quinolin-2-ylboronic acid has emerged as a valuable precursor in materials science. Its incorporation into conjugated systems has led to the development of novel materials with tailored electronic properties. For example, researchers have utilized this compound to synthesize advanced organic semiconductors, which exhibit improved charge transport characteristics. These materials hold promise for applications in flexible electronics and optoelectronic devices.

The latest studies on Quinolin-2-ylboronic acid have delved into its catalytic properties. Scientists have discovered that this compound can act as a ligand in transition metal-catalyzed reactions, enhancing reaction efficiency and selectivity. This dual role as both a substrate and a catalyst underscores its versatility and positions it as a multi-functional tool in modern organic synthesis.

In conclusion, Quinolin-2-ylboronic acid (CAS No. 745784-12-7) stands out as a pivotal compound in contemporary chemical research. Its structural features and reactivity make it indispensable for constructing complex molecules and advanced materials. As ongoing research continues to uncover new applications and optimize its synthesis, this compound is poised to play an even greater role in shaping future innovations across diverse scientific disciplines.

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