191162-39-7

Basic information

• Product Name: 3-Quinolineboronic acid
• Synonyms: CHEMBRDG-BB 4003837;3-QUINOLINEBORONIC ACID;3-QUINOLYL BORONIC ACID;3-QUINOLINYLBORONI ACID;3-QUINOLINYLBORONIC ACID;AKOS BRN-0151;RARECHEM AK VD 0023;QUINOLIN-3-YLBORONIC ACID
• CAS NO: 191162-39-7
• Molecular Formula: C₉H₈BNO₂
• Molecular Weight: 172.98
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Heterocycles;Boronic Acids & Esters;Quinolines, Isoquinolines & Quinoxalines;Boronic acid;Organoborons;Quinoline;B (Classes of Boron Compounds);Boronic Acids;Quinolinecarboxylic Acids, etc.;Quinolines;Boronic Acids & Esters;Quinolines, Isoquinolines & Quinoxalines;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronic Acids;Organometallic Reagents;OLED materials,pharm chemical,electronic;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate
• Mol File: 191162-39-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 148-155°C
• Boiling Point: 400.3 ºC at 760 mmHg
• Flash Point: 195.9 ºC
• Appearance: Light pink or orange to light brown/Powder
• Density: 1.28 g/cm³
• Vapor Pressure: 0.066mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Keep Cold
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.61±0.30(Predicted)
• BRN: 8764547
• CAS DataBase Reference: 3-Quinolineboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolineboronic acid(191162-39-7)
• EPA Substance Registry System: 3-Quinolineboronic acid(191162-39-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22-37-36
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 191162-39-7(Hazardous Substances Data)

Usage

Description

3-Quinolineboronic acid is a light pink or orange to light brown powder, which is a member of the boronic acid derivatives. It may contain varying amounts of anhydride and is known for its unique chemical properties, making it a versatile compound in various applications.

Uses

Used in Pharmaceutical Industry:
3-Quinolineboronic acid is used as a reactant for the preparation of P1-substituted symmetry-based human immunodeficiency virus (HIV) protease inhibitors. These inhibitors possess antiviral activity against drug-resistant viruses, making them a valuable asset in the fight against HIV.
Used in Chemical Synthesis:
3-Quinolineboronic acid is utilized as a reactant in the preparation of heterobiaryls via Suzuki-Miyaura cross-coupling with heteroaryl halides. This process is essential in the synthesis of various complex organic compounds, contributing to the development of new materials and pharmaceuticals.
Used in Fluorescence Sensing:
As a member of the boronic acid derivatives, 3-Quinolineboronic acid changes its fluorescence properties upon binding to sugar molecules. This characteristic makes it a potential candidate for the development of fluorescence-based sensors for detecting and analyzing sugar molecules in various applications.
Used in Bacterial Inhibition:
3-Quinolineboronic acid has shown potential as an inhibitor of the Staphylococcus aureus NorA efflux pump. This inhibition can help in the development of new antibiotics or treatment strategies against drug-resistant strains of bacteria, particularly those involving S. aureus.

InChI:InChI=1/C8H10BrNO/c1-3-11-8-7(9)4-6(2)5-10-8/h4-5H,3H2,1-2H3

Upstream product

• 5332-24-1 3-bromoquinoline 
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Downstream Products

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• 904325-85-5 3-biphenyl-4-ylquinoline 
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• 37045-16-2 3-benzylquinoline 
• 915019-65-7 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-propionitrile 
• 1033859-03-8 N-(4-fluorophenyl)-2,2-dimethyl-N-[(2-quinolin-3-yl-1,3-thiazol-4-yl)methyl]propanamide 
• 1062368-50-6 3-[6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline 
• 1103930-71-7 methyl 2-(2-(2-(4-benzhydrylpiperazin-1-yl)-2-oxoethoxy)acetamido)-5-(quinolin-3-yl)benzoate 
• 1138327-69-1 3-[4-(1-methyl-1-([3-(trifluoromethyl)phenyl]sulfonyl)ethyl)piperidin-1-yl]quinoline 

Relevant articles and documents

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

Investigation of a lithium-halogen exchange flow process for the preparation of boronates by using a cryo-flow reactor

Conducting low-temperature organometallic reactions under continuous flow conditions offers the potential to more accurately control exotherms and thus provide more reproducible and scalable processes. Herein, progress towards this goal with regards to the lithium-halogen exchange/borylation reaction is reported. In addition to improving the scope of substrates available on a research scale, methods to improve reaction profiles and expedite purification of the products are also described. On moving to a continuous system, thermocouple measurements have been used to track exotherms and provide a level of safety for continuous processing of organometallic reagents. The use of an in-line continuous liquid-liquid separation device to circumvent labour intensive downstream off-line processing is also reported. A cool setup: A small footprint, modular setup based around a cryo-flow reactor is reported for the preparation of gram quantities of boronic esters. With minimum alteration, including the addition of a data logger with thermocouples and a liquid-liquid separator, the same equipment can be used to scale the process, inclusive of an in-line extraction. Copyright