86-58-8 Usage
Description
8-Quinolineboronic acid is an organic compound with the chemical formula C9H8BNO2. It is a derivative of quinoline, a heterocyclic aromatic compound, and features a boronic acid functional group. 8-Quinolineboronic acid is known for its reactivity and stability, making it a versatile building block in organic synthesis.
Uses
Used in Suzuki Reaction:
8-Quinolineboronic acid is used as a reactant in Suzuki reactions for the formation of C-C bonds between aryl and vinyl halides or triflates and arylboronic acids. This palladium-catalyzed cross-coupling reaction is widely employed in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in C-H and C-S Bond Activations:
8-Quinolineboronic acid is used as a reactant involved in C-H and C-S bond activations, enabling the functionalization of unactivated carbon-hydrogen and carbon-sulfur bonds. This allows for the synthesis of diverse quinoline-containing compounds with potential applications in medicinal chemistry and materials science.
Used in Synthesis of Pyridazine:
8-Quinolineboronic acid is used as a building block in the synthesis of pyridazine via sequential amination, Suzuki coupling, and alkylation reactions. Pyridazine is a fused bicyclic compound with potential applications as a pharmaceutical intermediate and in the development of novel agrochemicals.
Used in Synthesis of Biaryl Monophosphorus Ligands:
8-Quinolineboronic acid is used as a reactant in Suzuki-Miyaura coupling reactions for the synthesis of biaryl monophosphorus ligands. These ligands are valuable in asymmetric catalysis, enabling the enantioselective synthesis of chiral compounds with potential applications in the pharmaceutical industry.
Used in Synthesis of Fused Tricyclic Oxa-Quinolones:
8-Quinolineboronic acid is used as a reactant in the synthesis of fused tricyclic oxa-quinolones, which are structurally diverse and exhibit a range of biological activities. These compounds have potential applications as anticancer agents, antimalarials, and antitubercular drugs.
Used in Synthesis of Substituted β-Amino Acids:
8-Quinolineboronic acid is used as a building block in the synthesis of substituted β-amino acids via Suzuki-Miyaura coupling reactions. These non-natural amino acids are valuable in the development of peptidomimetics, which can serve as bioactive molecules with potential applications in drug discovery.
Used in Copper-Catalyzed Azidation:
8-Quinolineboronic acid is used as a reactant in copper-catalyzed azidation with sodium azide, enabling the introduction of azide groups into organic molecules. This reaction can be used for the synthesis of various functionalized compounds, including those with potential applications in click chemistry.
Used in Studies of Fluoride Effects on Boronic Acid Stability:
8-Quinolineboronic acid is used as a model compound in studies investigating the effects of fluoride on the stability of boronic acids during click reactions. Understanding these effects can help optimize reaction conditions and improve the efficiency of click chemistry processes.
Check Digit Verification of cas no
The CAS Registry Mumber 86-58-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 86-58:
(4*8)+(3*6)+(2*5)+(1*8)=68
68 % 10 = 8
So 86-58-8 is a valid CAS Registry Number.
86-58-8Relevant articles and documents
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Letsinger,Dandegaonker
, p. 498,501 (1959)
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Silicon-bridged metallocene complex containing nitrogen heterocyclic ring structures and application thereof
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Paragraph 0045-0048, (2020/06/04)
The invention relates to a preparation method and application of an olefin polymerization reaction catalyst, in particular to a silicon-bridged metallocene complex with nitrogen heterocyclic ring structures and application thereof. Molecules of the designed novel silicon-bridged metallocene complex contain three different nitrogen heterocyclic ring structures, and the distances from nitrogen atomsto a metal center are different, so that different chemical environments are provided for the metal center, and the metallocene complex with a novel structure is constructed. By changing a skeleton structure and a substituent group, the three-dimensional effect and the electronic effect of the metallocene complex can be conveniently regulated and controlled, the catalytic performance is regulatedand controlled, and polyolefin high polymer materials with different structures and properties are prepared.
Pyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia
Abrunhosa-Thomas, Isabelle,Anizon, Fabrice,Artola, Alain,Dallel, Radhouane,Descheemaeker, Amélie,Giraud, Francis,Moreau, Pascale,Nauton, Lionel,Pinto-Pardo, Nicolas,Théry, Vincent,Visseq, Alexia
, (2019/12/24)
Mechanical Allodynia (MA), a frequent chronic pain symptom caused by innocuous stimuli, constitutes an unmet medical need, as treatments using analgesics available today are not always effective and can be associated with important side-effects. A series of 3,5-disubstituted pyridin-2(1H)-ones was designed, synthesized and evaluated in vivo toward a rat model of inflammatory MA. We found that the series rapidly and strongly prevented the development of MA. 3-(2-Bromophenyl)-5-(phenylamino)pyridin-2(1H)-one 69, the most active compound of the series, was also able to quickly reverse neuropathic MA in rats. Next, when 69 was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biological target(s), we found that 69 is a p38α MAPK inhibitor, a PK known to contribute to pain hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones thus could represent a novel class of analgesic for the treatment of MA.
