3-Quinolineboronic acid

Base Information

• Chemical Name: 3-Quinolineboronic acid
• CAS No.: 191162-39-7
• Molecular Formula: C9H8BNO2
• Molecular Weight: 172.979
• Hs Code.: 29334900
• European Community (EC) Number: 640-162-5
• DSSTox Substance ID: DTXSID60370433
• Nikkaji Number: J1.751.727I
• Wikidata: Q72505803
• ChEMBL ID: CHEMBL3236629
• Mol file: 191162-39-7.mol

Synonyms:3-quinolineboronic acid;191162-39-7;Quinoline-3-boronic Acid;Quinolin-3-ylboronic Acid;3-quinolylboronic acid;3-quinolinylboronic acid;Boronic acid, 3-quinolinyl-;MFCD02183527;(quinolin-3-yl)boronic acid;Quinoline-3-boronicacid;3-Quinoline boronic acid;quinolin-3-boronic acid;3-Quinolinyl-boronic acid;quinolin-3-yl-boronic acid;quinoline-3-yl boronic acid;SCHEMBL20226;Boronic acid, B-3-quinolinyl-;CHEMBL3236629;YGDICLRMNDWZAK-UHFFFAOYSA-;DTXSID60370433;YGDICLRMNDWZAK-UHFFFAOYSA-N;BCP21925;AKOS003237476;CS-W002923;GS-6504;OL10102;PB21802;SB20064;3-Quinolineboronic acid, technical grade;AC-27324;SY004117;A4218;AM20050916;FT-0616380;Q0080;EN300-31679;J-012350;J-513104;J-521587;F0001-2468;Z330820004;InChI=1/C9H8BNO2/c12-10(13)8-5-7-3-1-2-4-9(7)11-6-8/h1-6,12-13H

Chemical Property of 3-Quinolineboronic acid

Chemical Property:

• Appearance/Colour: light pink or orange to light brown powder
• Vapor Pressure: 0.066mmHg at 25°C
• Melting Point: 148-155 ºC
• Refractive Index: 1.531
• Boiling Point: 400.3 ºC at 760 mmHg
• PKA: 4.61±0.30(Predicted)
• Flash Point: 195.9 ºC
• PSA: 53.35000
• Density: 1.28 g/cm³
• LogP: -0.08540
• Storage Temp.: Keep Cold
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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

3-Quinoline boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22-37-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=CC=CC=C2N=C1)(O)O
• Uses: 3-Quinolineboronic acid can be used as a reactant for: Preparation of P1-substituted symmetry-based human immunodeficiency virus protease inhibitors with antiviral activity against drug-resistant viruses Preparation of heterobiaryls via Suzuki-Miyaura cross-coupling with heteroaryl halides in co 3-Quinolineboronic acid is a member of a group of boronic acid derivatives that change fluorescence properties once they are bound to sugar molecules. 3-Quinolineboronic acid is also a potential inhibitor of the Staphylococcus aureus NorA efflux pump.

Technology Process of 3-Quinolineboronic acid

There total 7 articles about 3-Quinolineboronic 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: 90.0%

3-bromoquinoline (5332-24-1) → quinolin-3-ylboronic acid (191162-39-7)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.dyepig.2013.04.021

Reference yield: 72.0%

3-bromoquinoline (5332-24-1) + Triisopropyl borate (5419-55-6) → quinolin-3-ylboronic acid (191162-39-7)

Guidance literature:

3-bromoquinoline; Triisopropyl borate; With n-butyllithium; In tetrahydrofuran; at -75 - 0 ℃; for 0.333333h;

With hydrogenchloride; water; In tetrahydrofuran;

Reference yield: 37.0%

tetrahydroxydiboron (13675-18-8) + 1H-pyrazole-3-diazonium tetrafluoroborate → quinolin-3-ylboronic acid (191162-39-7)

Guidance literature:

In water; N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

DOI:10.1002/chem.201402487

upstream raw materials:

3-bromoquinoline

Trimethyl borate

Triisopropyl borate

3-aminoquinoline

Downstream raw materials:

3-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)quinoline

1-(4-(piperazin-1-ylsulfonyl)phenyl)-9-(quinolin-3-yl)benzo[h][1,6]naphthyridin-2(1H)-one

1-(4-(4-aminopiperidin-1-yl)-2-methoxyphenyl)-9-(quinolin-3-yl)benzo[h][1,6]naphthyridin-2(1H)-one

1-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-9-(quinolin-3-yl)benzo[h][1,6]naphthyridin-2(1H)-one

Refernces

• 1、 -. "MULTICYCLIC COMPOUND INCLUDING NITROGEN AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME". Paragraph 0151-0154. . Retrieved 2016/10/08.
• 2、 Erb, William,Hellal, Akila,Albini, Mathieu,Rouden, Jacques,Blanchet, Jerome. "An easy route to (hetero)arylboronic acids". . p. 6608 - 6612. Retrieved 2014/06/09.