Quinoline-5-boronic acid

Base Information

• Chemical Name: Quinoline-5-boronic acid
• CAS No.: 355386-94-6
• Molecular Formula: C9H8BNO2
• Molecular Weight: 172.979
• Hs Code.: 29334900
• European Community (EC) Number: 670-357-0
• DSSTox Substance ID: DTXSID90408935
• Nikkaji Number: J2.439.022E
• Wikidata: Q72505806
• Mol file: 355386-94-6.mol

Synonyms:5-quinolineboronic acid

Chemical Property of Quinoline-5-boronic acid

Chemical Property:

• Vapor Pressure: 3.99E-07mmHg at 25°C
• Melting Point: 144-148 °C
• Refractive Index: 1.644
• Boiling Point: 400.3 °C at 760 mmHg
• PKA: 7.46±0.30(Predicted)
• Flash Point: 195.9 °C
• PSA: 53.35000
• Density: 1.28 g/cm³
• LogP: -0.08540
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 173.0648087
• Heavy Atom Count: 13
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

Quinoline-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C2C=CC=NC2=CC=C1)(O)O

Technology Process of Quinoline-5-boronic acid

There total 4 articles about Quinoline-5-boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

5-bromoquinoline (4964-71-0) + Triisopropyl borate (5419-55-6) → quinolin-5-ylboronic acid (355386-94-6)

Guidance literature:

5-bromoquinoline; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at 20 ℃;

Reference yield: 45.0%

5-bromoquinoline (4964-71-0) + Trimethyl borate (121-43-7,63156-11-6) → quinolin-5-ylboronic acid (355386-94-6)

Guidance literature:

5-bromoquinoline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.3987/COM-05-10496

Reference yield:

5-bromoquinoline (4964-71-0) → quinolin-5-ylboronic acid (355386-94-6)

Guidance literature:

With tetrahydroxydiboron; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine; In ethanol; at 80 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1021/jo401104y

upstream raw materials:

5-bromoquinoline

Trimethyl borate

Triisopropyl borate

water

Downstream raw materials:

5-(trifluoro-λ4-boraneyl)quinoline potassium salt

C₃₁H₁₈F₆N₄O₂

methyl 2-(4-methyl-2-(quinolin-5-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

ML₃₄₇

Refernces

• 1、 -. "Composite taken as URAT 1 inhibitor". Paragraph 0014; 0016. . Retrieved 2018/05/16.
• 2、 Lee, Ihl Young Choi,Jung, Myung Hee,Lim, Hee-Jeong,Lee, Hyo Won. "Synthesis of quinolyl- and isoquinolyl heteroarylamines using palladium catalyzed suzuki cross-coupling reaction". . p. 2505 - 2511. Retrieved 2007/10/03.