6-Iodoquinoline

Base Information

• Chemical Name: 6-Iodoquinoline
• CAS No.: 13327-31-6
• Molecular Formula: C9H6IN
• Molecular Weight: 255.058
• Hs Code.: 29334900
• European Community (EC) Number: 663-773-9
• DSSTox Substance ID: DTXSID20928030
• Nikkaji Number: J3.508.197F
• Wikidata: Q72484614
• Mol file: 13327-31-6.mol

Synonyms:6-Iodoquinoline;13327-31-6;Quinoline, 6-iodo-;6-iodo-quinoline;MFCD08457906;SCHEMBL359732;DTXSID20928030;WKTASELJZCIVBR-UHFFFAOYSA-N;AKOS005146263;CS-W003518;PS-7410;SB71563;SY030914;DB-011494;AM20070127;EN300-73850;A23334;A1-00823;J-518817;Z993990690

Chemical Property of 6-Iodoquinoline

Chemical Property:

• Vapor Pressure: 0.000585mmHg at 25°C
• Melting Point: 91°C
• Refractive Index: 1.724
• Boiling Point: 320.71 °C at 760 mmHg
• PKA: 4.23±0.10(Predicted)
• Flash Point: 147.76 °C
• PSA: 12.89000
• Density: 1.837 g/cm³
• LogP: 2.83940
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 254.95450
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

6-Iodoquinolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2)I)N=C1
• Uses: Reactant for:Room temperature CuI-catalyzed N-arylation using 2-pyridinyl β-ketones ligands

Technology Process of 6-Iodoquinoline

There total 8 articles about 6-Iodoquinoline 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: 97.0%

6-bromoquinoline (5332-25-2) → 6-iodoquinoline (13327-31-6)

Guidance literature:

With copper(l) iodide; cis-N,N'-dimethyl-1,2-diaminocyclohexane; sodium iodide; In 1,4-dioxane; at 110 ℃; for 15h; Sealed tube;

Reference yield: 91.0%

6-iodoquinoline N-oxide → 6-iodoquinoline (13327-31-6)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In acetonitrile; at 20 ℃; for 0.0833333h; chemoselective reaction; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.0c02805

Reference yield: 79.0%

6-aminoquinoline (580-15-4) → 6-iodoquinoline (13327-31-6)

Guidance literature:

6-aminoquinoline; With trifluorormethanesulfonic acid; sodium nitrite; In hexane; dimethyl sulfoxide; at 5 - 20 ℃; for 1h;

With potassium iodide; In hexane; water; dimethyl sulfoxide; at 20 ℃; for 0.166667h;

DOI:10.1055/s-0035-1560392

upstream raw materials:

6-bromoquinoline

6-aminoquinoline

4-iodophenylboronic acid

p-aminoiodobenzene

Downstream raw materials:

ethyl 2,2-difluoro-2-(quinolin-6-yl)acetate

C₁₅H₁₀BrNO

6-(2-(3,3-dimethylbut-1-ynyl)phenyl)quinolin-2-amine

6-(2-bromophenyl)-N-tert-butylquinolin-2-amine

Refernces

• 1、 Kim, Kyu Dong,Lee, Jun Hee. "Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides". supporting information. p. 7712 - 7716. Retrieved 2019/01/03.
• 2、 Kassanova, Assiya Zh.,Krasnokutskaya, Elena A.,Beisembai, Perizat S.,Filimonov, Victor D.. "A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution". . p. 256 - 262. Retrieved 2016/01/15.