8-Quinolineboronic acid

Base Information

• Chemical Name: 8-Quinolineboronic acid
• CAS No.: 86-58-8
• Molecular Formula: C9H8BNO2
• Molecular Weight: 172.979
• Hs Code.: 29339900
• European Community (EC) Number: 626-756-7
• UNII: 5QS1A25IJ6
• DSSTox Substance ID: DTXSID00370270
• Nikkaji Number: J2.010.463E
• Wikidata: Q27262755
• Mol file: 86-58-8.mol

Synonyms:8-quinolineboronic acid

Chemical Property of 8-Quinolineboronic acid

Chemical Property:

• Appearance/Colour: yellow crystal powder
• Melting Point: 350 °C
• Boiling Point: 400.261 °C at 760 mmHg
• PKA: 4.61±0.30(Predicted)
• Flash Point: 195.871 °C
• PSA: 53.35000
• Density: 1.289 g/cm³
• LogP: -0.08540
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• 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-8-boronicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=C2C(=CC=C1)C=CC=N2)(O)O
• Uses: suzuki reaction Reactant involved in:C-H and C-S bond activationsSynthesis of pyridazine via sequential amination / Suzuki coupling / alkylation reactionsSuzuki-Miyaura coupling reactions for synthesis of biaryl monophosphorus ligands, fused tricyclic oxa-quinolones, or substituted β-amino acidsCopper-catalyzed azidation with sodium azideStudies of the affect of fluoride on the stability of boronic acids during click reactions

Technology Process of 8-Quinolineboronic acid

There total 9 articles about 8-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: 87.0%

8-bromoquinoline (16567-18-3) + Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) → 8-quinolinylboronic acid (86-58-8)

Guidance literature:

8-bromoquinoline; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 16h;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 16h;

water; In tetrahydrofuran; at 0 ℃;

Reference yield: 64.0%

8-bromoquinoline (16567-18-3) + Triisopropyl borate (5419-55-6) → 8-quinolinylboronic acid (86-58-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -60 ℃; Flow reactor;

DOI:10.1002/chem.201303736

Reference yield: 60.0%

8-bromoquinoline (16567-18-3) → 8-quinolinylboronic acid (86-58-8)

Guidance literature:

8-bromoquinoline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

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

With hydrogenchloride; In tetrahydrofuran; hexane;

DOI:10.1021/jo026850+

upstream raw materials:

8-bromoquinoline

boric acid tributyl ester

8-amino quinoline

Triisopropyl borate

Downstream raw materials:

4-({4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-phenyl}-quinolin-8-yl-methylene)-piperidine-1-carboxylic acid tert-butyl ester

8-[6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline

N-(2,5-dimethoxybenzyl)-2,6-di(quinolin-8-yl)isonicotinamide

8-(2,6-dimethoxyphenyl)quinoline

Refernces

• 1、 -. "NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN". Page/Page column 15; 23. . Retrieved 2021/04/10.
• 2、 -. "Silicon-bridged metallocene complex with C2 symmetrical structure and application thereof". Paragraph 0037-0040. . Retrieved 2020/06/09.