Quinoline-6-boronic acid

Base Information

• Chemical Name: Quinoline-6-boronic acid
• CAS No.: 376581-24-7
• Molecular Formula: C₉H₈BNO₂
• Molecular Weight: 172.979
• Hs Code.: 29334990
• European Community (EC) Number: 691-953-7
• DSSTox Substance ID: DTXSID40400626
• Nikkaji Number: J2.725.429B
• Wikidata: Q72505813
• Mol file: 376581-24-7.mol

Synonyms:Boronicacid, 6-quinolinyl- (9CI);Quinolin-6-ylboronic acid;Quinoline-6-boronic acid;

Chemical Property of Quinoline-6-boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 106-109°C
• Refractive Index: 1.645
• Boiling Point: 400.261 °C at 760 mmHg
• PKA: 7.70±0.30(Predicted)
• Flash Point: 195.871 °C
• PSA: 53.35000
• Density: 1.289 g/cm³
• LogP: -0.08540
• Storage Temp.: Keep Cold
• Water Solubility.: Slightly soluble in water.
• 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-6-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)N=CC=C2)(O)O
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of Quinoline-6-boronic acid

There total 4 articles about Quinoline-6-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: 86.4%

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline (406463-06-7) → 6-quinolineboronic acid (376581-24-7)

Guidance literature:

With hydrogenchloride; at 50 ℃; for 0.5h;

Reference yield:

6-bromoquinoline hydrochloride + water (7732-18-5) + bis(pinacol)diborane (73183-34-3) → 6-quinolineboronic acid (376581-24-7)

Guidance literature:

6-bromoquinoline hydrochloride; bis(pinacol)diborane; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere; Sealed tube;

water; In ethyl acetate;

Reference yield:

6-bromoquinoline (5332-25-2) + Trimethyl borate (121-43-7,63156-11-6) → 6-quinolineboronic acid (376581-24-7)

Guidance literature:

6-bromoquinoline; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.6b01681

upstream raw materials:

6-bromoquinoline

Trimethyl borate

water

bis(pinacol)diborane

Downstream raw materials:

6-benzylquinoline

Refernces

• 1、 -. "Preparation method of benzoheterocyclic boric acid". Paragraph 0062; 0064; 0066. . Retrieved 2018/09/13.
• 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.