376581-24-7

Basic information

• Product Name: Quinoline-6-boronic acid
• Synonyms: QUINOLINE-6-BORONIC ACID;QUINOLIN-6-YLBORONIC ACID;CHEMBRDG-BB 4202093;AKOS BRN-0348;Boronic acid, 6-quinolinyl- (9CI);6-Quinolineboronicaid;6-QUINOLINBORONIC ACID;Quinaline-6-boronic acid
• CAS NO: 376581-24-7
• Molecular Formula: C9H8BNO2
• Molecular Weight: 172.98
• EINECS: -0
• Product Categories: BORONICACID;blocks;BoronicAcids;Quinolines;pharmacetical;Boronic Acid;quinoline
• Mol File: 376581-24-7.mol

Chemical Properties

• Melting Point: 106-109°C
• Boiling Point: 400.261 °C at 760 mmHg
• Flash Point: 195.871 °C
• Appearance: White/Crystalline Powder
• Density: 1.289 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Keep Cold
• PKA: 7.70±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Quinoline-6-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline-6-boronic acid(376581-24-7)
• EPA Substance Registry System: Quinoline-6-boronic acid(376581-24-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36/38-22
• Safety Statements: 26-36/37/39-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 376581-24-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Quinoline-6-boronic acid is used as a key intermediate for the synthesis of complex organic molecules. Its boronic acid functionality allows for versatile reactions, such as Suzuki-Miyaura cross-coupling, which is widely employed in the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, quinoline-6-boronic acid is utilized as a starting material or intermediate in the development of new drugs. Its unique structure and reactivity enable the creation of novel therapeutic agents with potential applications in various medical fields.
Used in Agrochemicals:
Quinoline-6-boronic acid is also employed in the agrochemical industry as a building block for the synthesis of pesticides, herbicides, and other crop protection agents. Its incorporation into these compounds can lead to improved efficacy and selectivity, ultimately contributing to more effective and environmentally friendly agricultural practices.
Used in Dyestuff:
In the dyestuff industry, quinoline-6-boronic acid is used as a precursor for the synthesis of various dyes and pigments. Its ability to form a range of colored compounds makes it a valuable asset in the development of new colorants for various applications, including textiles, plastics, and printing inks.

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

Upstream product

• 406463-06-7 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline 
• 7732-18-5 water 
• 73183-34-3 bis(pinacol)diborane 
• 5332-25-2 6-bromoquinoline 
• 121-43-7 Trimethyl borate 

Downstream Products

• 54884-99-0 6-benzylquinoline 

Relevant articles and documents

Preparation method of benzoheterocyclic boric acid

The invention provides a preparation method of benzoheterocyclic boric acid. The preparation method comprises steps as follows: (1) a benzoheterocyclic compound shown in a formula I is dissolved in asolvent A, a liquor A is obtained, a boronylation reagent is dissolved in a solvent B, a liquor B is obtained, a palladium catalyst and an alkaline reagent are immobilized on a channel of a continuousflow reactor, the liquor A and the liquor B are subjected to a continuous adding reaction, the reaction is stopped after the mixture flows out of a reaction tube, and an intermediate is obtained; (2)the intermediate obtained in step (1) is subjected to a hydrolysis reaction, and benzoheterocyclic boric acid is obtained. According to the provided preparation method, the benzoheterocyclic boric acid is synthesized with a flow chemical technology. Compared with methods in the prior art, the method has the advantages that the product yield is 86% or above, the highest yield can reach 90% or above, the yield is very high, the reaction rate is high, energy consumption of a reaction is reduced greatly, and the method is high in operability, high in automation degree and favorable for productionoperation and industrial production.

DERIVATIVES OF QUINOLINE AS INHIBITORS OF DYRK1A AND/OR DYRK1B KINASES

The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

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.