355386-94-6

Basic information

• Product Name: Quinoline-5-boronic acid
• Synonyms: 5-QUINOLINEBORONIC ACID;AKOS BRN-0681;CHEMBRDG-BB 4202092;QUINOLIN-5-YLBORONIC ACID;QUINOLINE-5-BORONIC ACID;Boronic acid, 5-quinolinyl- (9CI);5-QUINOLINBORONIC ACID;QUINOLIN-5-YL-5-BORONIC ACID
• CAS NO: 355386-94-6
• Molecular Formula: C₉H₈BNO₂
• Molecular Weight: 172.98
• EINECS: -0
• Product Categories: BORONICACID;Boronic Acid;Organoborons;Quinoline
• Mol File: 355386-94-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 144-148°C
• Boiling Point: 400.3 °C at 760 mmHg
• Flash Point: 195.9 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 3.99E-07mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.46±0.30(Predicted)
• CAS DataBase Reference: Quinoline-5-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline-5-boronic acid(355386-94-6)
• EPA Substance Registry System: Quinoline-5-boronic acid(355386-94-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39-37
• HazardClass: IRRITANT
• Hazardous Substances Data: 355386-94-6(Hazardous Substances Data)

Usage

General Description

Quinoline-5-boronic acid is a chemical compound with the molecular formula C9H8BNO2. It is a boronic acid derivative of quinoline, a heterocyclic aromatic compound. This chemical is commonly used as a building block in organic synthesis and pharmaceutical research. It is known for its ability to form coordination complexes with other molecules, and is often used in the development of new drugs and agrochemicals. Quinoline-5-boronic acid is also used in the production of OLEDs (organic light-emitting diodes) and other electronic materials due to its versatile properties and compatibility with various organic molecules.

InChI:InChI=1/C9H8BNO2/c12-10(13)8-4-1-5-9-7(8)3-2-6-11-9/h1-6,12-13H

Upstream product

• 4964-71-0 5-bromoquinoline 
• 5419-55-6 Triisopropyl borate 
• 7732-18-5 water 
• 121-43-7 Trimethyl borate 

Downstream Products

• 1411985-86-8 5-(trifluoro-λ4-boraneyl)quinoline potassium salt 
• 1612182-17-8 4-N-[2-(4-chlorophenyl)ethyl]-6-(quinolin-5-yl)pyrimidine-2,4-diamine 
• 16675-62-0 methyl quinoline-5-carboxylate 

Relevant articles and documents

Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates

We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox. We demonstrate the broad scope, scalability, and robustness of this unconventional catalyst-free transformation, leading to functionalized biaryls and ultimately furnishing drug-like small molecules, as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental investigations.

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.