Quinoline-4-boronic acid

Base Information

• Chemical Name: Quinoline-4-boronic acid
• CAS No.: 371764-64-6
• Molecular Formula: C9H8BNO2
• Molecular Weight: 172.979
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID80376417
• Wikidata: Q72505809
• Mol file: 371764-64-6.mol

Synonyms:371764-64-6;QUINOLINE-4-BORONIC ACID;Quinolin-4-ylboronic Acid;4-Quinolineboronic acid;(quinolin-4-yl)boronic acid;BORONIC ACID, 4-QUINOLINYL-;MFCD03095174;quinolin-4-yl-4-boronic acid;4-quinolyl boronic acid;Quinolin-4-ylboronicAcid;SCHEMBL482068;DTXSID80376417;KATIRQRAVXTBNY-UHFFFAOYSA-N;quinoline-4-boronic acid, AldrichCPR;AKOS005258928;AB13541;AC-6958;CS-W000919;DS-12706;SY003948;A6385;AM20051122;FT-0603703;EN300-212552;Z1198161562

Chemical Property of Quinoline-4-boronic acid

Chemical Property:

• Vapor Pressure: 3.99E-07mmHg at 25°C
• Refractive Index: 1.644
• Boiling Point: 400.3 °C at 760 mmHg
• PKA: 3.70±0.30(Predicted)
• Flash Point: 195.9 °C
• PSA: 53.35000
• Density: 1.28 g/cm³
• LogP: -0.08540
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• 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

4-QuinolineboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39-37

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC=NC2=CC=CC=C12)(O)O
• Uses: 4-Quinolineboronic Acid is a reactant in the synthesis of NSC 12155, a small molecule inhibitor of anthrax lethal factor toxin.

Technology Process of Quinoline-4-boronic acid

There total 5 articles about Quinoline-4-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: 53.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-bromoquinoline (3964-04-3,850917-90-7) → quinolin‐4‐ylboronic acid (371764-64-6)

Guidance literature:

4-bromoquinoline; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; at 20 ℃;

Reference yield:

bis(pinacol)diborane (73183-34-3) + 4-bromoquinoline (3964-04-3,850917-90-7) → quinolin‐4‐ylboronic acid (371764-64-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 2h; Inert atmosphere;

Reference yield:

Triisopropyl borate (5419-55-6) + 4-bromoquinoline (3964-04-3,850917-90-7) → quinolin‐4‐ylboronic acid (371764-64-6)

Guidance literature:

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

Triisopropyl borate; In tetrahydrofuran; at 20 ℃;

upstream raw materials:

4-bromoquinoline

bis(pinacol)diborane

Triisopropyl borate

Trimethyl borate

Downstream raw materials:

potassium trifluoro(quinolin-4-yl)borate

quinoline-4-carboxylic acid methyl ester

Refernces

• 1、 -. "Thiophene derivatives used as inhibitor of URAT1". Paragraph 0178; 0180; 0181; 0182. . Retrieved 2019/04/26.
• 2、 Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina. "Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]". . p. 6427 - 6439. Retrieved 2013/07/26.