171364-85-5

Basic information

• Product Name: QUINOLINE-3-BORONIC ACID PINACOLATE
• Synonyms: QUINOLINE-3-BORONIC ACID PINACOLATE;AKOS BRN-1143;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)QUINOLINE;3-QUINOLINEBORONIC ACID PINACOL ESTER, 97%;QUINOLINE-3-BORONIC ACID PINACOL ESTER;quinoline-boronic acid pinacol ester;Quinoline, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;3-hydroxy-2,3-diMethylbutan-2-yl hydrogen quinolin-3-ylboronate
• CAS NO: 171364-85-5
• Molecular Formula: C₁₅H₁₈BNO₂
• Molecular Weight: 255.12
• Product Categories: API intermediates;Boronic Acid
• Mol File: 171364-85-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 56-60 °C(lit.)
• Boiling Point: 386.468 °C at 760 mmHg
• Flash Point: 187.53 °C
• Appearance: White to pale brown/Powder or Solid
• Density: 1.101 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 5.12±0.12(Predicted)
• CAS DataBase Reference: QUINOLINE-3-BORONIC ACID PINACOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINOLINE-3-BORONIC ACID PINACOLATE(171364-85-5)
• EPA Substance Registry System: QUINOLINE-3-BORONIC ACID PINACOLATE(171364-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 171364-85-5(Hazardous Substances Data)

Usage

Description

QUINOLINE-3-BORONIC ACID PINACOLATE, also known as 3-Quinolineboronic Acid Pinacol Ester, is an organic compound that serves as a versatile reagent in the field of chemical synthesis. It is characterized by its unique chemical structure, which includes a quinoline ring and a boronic acid group, making it a valuable component in the creation of various complex molecules.

Uses

Used in Pharmaceutical Industry:
QUINOLINE-3-BORONIC ACID PINACOLATE is used as a synthetic reagent for the production of 11-(pyridinylphenyl)steroids, which are a novel class of mixed progesterone agonists/antagonists. These compounds have potential applications in the development of new drugs for the treatment of various hormonal disorders and conditions related to the progesterone receptor.
In the synthesis process, QUINOLINE-3-BORONIC ACID PINACOLATE plays a crucial role in the formation of the desired steroidal structure, allowing for the creation of molecules with specific biological activities. Its use in this application highlights its importance in the development of innovative pharmaceuticals and contributes to the advancement of medical treatments.

InChI:InChI=1/C15H18BNO2/c1-14(2)15(3,4)19-16(18-14)12-9-11-7-5-6-8-13(11)17-10-12/h5-10H,1-4H3

Upstream product

• 91-22-5 quinoline 
• 73183-34-3 bis(pinacol)diborane 
• 580-17-6 3-aminoquinoline 
• 5332-24-1 3-bromoquinoline 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 79476-07-6 3-Iodoquinoline 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 

Downstream Products

• 1386394-19-9 3-(1-(cyclohex-1-en-1-yl)ethyl)quinoline 
• 1360628-88-1 3-fluoro-4-(7-methoxy-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile 
• 1448538-36-0 3-[4-benzyl-5-(phenylsulfanyl)-4H-1,2,4-triazol-3-yl]quinoline 
• 1454654-29-5 (4-morpholin-4-yl-phenyl)-(5-quinolin-3-yl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-amine 
• 1201646-91-4 2-methyl-2-(4-((3'-nitro[3,6-biquinolin]-4'-yl)amino)-phenyl)propanenitrile 
• 34846-64-5 3-cyanoquinoline 
• 1448812-68-7 N-(3-chloro-5-(((4-cyano-3-methyl-1-(3-(quinolin-3-yl)phenyl)-1H-pyrazol-5-yl)amino)methyl)-2-hydroxyphenyl)propionamide 

Relevant articles and documents

Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates

The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80-100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromatics was also achieved by using an almost equimolar amount of substrates and the diboron.

Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4?-/S42- and S3?-/S32- redox couples.

Efficient Synthesis of Aryl Boronates via Cobalt-Catalyzed Borylation of Aryl Chlorides and Bromides

An efficient catalytic system based on a Co(II)-NHC precursor has been developed for the cross coupling of bis(pinacolato)diboron with aryl halides including aryl chlorides, affording the aryl boronates in good to excellent yields. A wide range of functional groups are tolerated under mild reaction conditions. The reaction shows excellent chemoselectivity for bromide over chloride. Preliminary mechanistic investigations show that the catalytic cycle may rely on a cobalt(I)-(III) redox couple.