8-Bromoquinoline

Base Information

• Chemical Name: 8-Bromoquinoline
• CAS No.: 16567-18-3
• Molecular Formula: C9H6BrN
• Molecular Weight: 208.057
• Hs Code.: 29334900
• European Community (EC) Number: 630-629-1
• DSSTox Substance ID: DTXSID10168009
• Nikkaji Number: J903.987B
• Wikidata: Q72512461
• Mol file: 16567-18-3.mol

Synonyms:8-Bromoquinoline;16567-18-3;Quinoline, 8-bromo-;8-Bromo-quinoline;MFCD00191859;8-Bromoquinoline #;8-Bromoquinoline, 98%;SCHEMBL196509;2-aminothiazole-4-ethyl formate;DTXSID10168009;BCP27253;BBL020683;STK893373;AKOS001476139;AB04626;AC-1231;CS-W002501;FS-2279;ethyl-2-aminothiazole-4-carboxylic acid;SY014149;AM20070091;BB 0260004;FT-0601183;EN300-55898;A851039;W-205946;Z839152792

Chemical Property of 8-Bromoquinoline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 58-59 ºC
• Refractive Index: n20/D 1.672(lit.)
• Boiling Point: 303 ºC at 760 mmHg
• PKA: 2.33±0.17(Predicted)
• Flash Point: 132.8 ºC
• PSA: 12.89000
• Density: 1.565 g/cm³
• LogP: 2.99730
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Light Sensitive
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 206.96836
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

8-Bromoquinoline ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)N=CC=C2
• Uses: 8-Bromoquinoline may be used in the following studies:Synthesis of 8-(dimesitylboryl)quinolone (ambiphilic molecule).Direct synthesis of 5H-pyrido[3,2,1-ij]quinolin-3-one, via palladium catalyzed coupling reaction with acrolein.Preparation of 8-(1-hydroxyethyl)quinolone.Preparation of 8-quinolylcyclopentadienyl metal complexes, via reaction with zincated cyclopentadienyl derivatives of Fe, Mn and Re in the presence of bis(triphenylphosphine)palladium(0).Synthesis of n,n′-biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex.

Technology Process of 8-Bromoquinoline

There total 22 articles about 8-Bromoquinoline 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: 92.0%

8-bromoquinoline N-oxide (90279-39-3) → 8-bromoquinoline (16567-18-3)

Guidance literature:

With phenylboronic acid; In 1,2-dichloro-ethane; at 120 ℃; for 8h; Sealed tube;

DOI:10.1021/acs.joc.9b01538

Reference yield: 90.0%

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

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In water; at 100 ℃; Sealed tube;

DOI:10.1016/j.tetlet.2020.152738

Reference yield: 86.0%

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) + 2-bromoaniline (615-36-1) → 8-bromoquinoline (16567-18-3)

Guidance literature:

With methanesulfonic acid; iron(II) sulfate; sodium 3-nitrobenzenesulfonate; In water; at 125 ℃; Inert atmosphere;

DOI:10.1021/ja8066308

upstream raw materials:

glycerol

2-bromoaniline

quinoline

sulfuric acid

Downstream raw materials:

quinoline

8-quinolinylboronic acid

8-bromo-5-nitroquinoline

8-(2-Hydroxyethyl)quinoline

Refernces

• 1、 Wang, Jie,Chen, Mu-Wang,Ji, Yue,Hu, Shu-Bo,Zhou, Yong-Gui. "Kinetic Resolution of Axially Chiral 5- or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation". . p. 10413 - 10416. Retrieved 2016.
• 2、 Demianets, Ivan,Hunt, Jonathan R.,Dawlaty, Jahan M.,Williams, Travis J.. "Optical p Ka Control in a Bifunctional Iridium Complex". . p. 200 - 204. Retrieved 2019.
• 3、 Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar. "Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group". . p. 5870 - 5875. Retrieved 2020.