6-Methoxyquinoline

Base Information

• Chemical Name: 6-Methoxyquinoline
• CAS No.: 5263-87-6
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 29334990
• European Community (EC) Number: 226-077-2
• NSC Number: 1954
• UNII: 5S1U3125AD
• DSSTox Substance ID: DTXSID9063746
• Nikkaji Number: J54.285G
• Wikidata: Q27140168
• Metabolomics Workbench ID: 66130
• ChEMBL ID: CHEMBL15200
• Mol file: 5263-87-6.mol

Synonyms:6-methoxyquinoline;6-methoxyquinoline hydrochloride

Chemical Property of 6-Methoxyquinoline

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0.00272mmHg at 25°C
• Melting Point: 18-20 °C(lit.)
• Refractive Index: n20/D 1.625(lit.)
• Boiling Point: 295.3 °C at 760 mmHg
• PKA: 5.03(at 20℃)
• Flash Point: 102.7 °C
• PSA: 22.12000
• Density: 1.13 g/cm³
• LogP: 2.24340
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: soluble in Alcohol
• Water Solubility.: insoluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

6-Methoxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: COC1=CC2=C(C=C1)N=CC=C2
• Uses: 6-Methoxyquinoline is a useful sythetic intermediate 6-Methoxyquinoline is used as a precursor in the synthesis of:Fluorescent zinc and chlorine sensors.5-Amino-2-aroylquinolines as potent tubulin polymerization inhibitors.3-Fluoro-6-methoxyquinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase.Cobalt-based ternary metal-organic complex as single?ion magnets.

Technology Process of 6-Methoxyquinoline

There total 50 articles about 6-Methoxyquinoline 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: 99.0%

6-methoxyquinoline N-oxide (6563-13-9) → 6-methoxy quinoline (5263-87-6)

Guidance literature:

With C₅₅H₃₈F₅P₃Rh⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); isopropyl alcohol; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.organomet.9b00778

Reference yield: 99.0%

6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0) → 6-methoxy quinoline (5263-87-6)

Guidance literature:

With [Ru(1,10-phenanthroline-5,6-dione)₃](PF₆)₂; oxygen; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 27 ℃; for 72h; under 760.051 Torr;

DOI:10.1021/ja506546w

Reference yield: 93.0%

1-methanesulfonyl-6-methoxy-1,2-dihydro-quinoline (333383-86-1) → 6-methoxy quinoline (5263-87-6)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 0.5h;

upstream raw materials:

6-hydroxyquinoline

methyl iodide

4-methoxyacetanilide

glycerol

Downstream raw materials:

1-benzoyl-6-methoxy-1,2-dihydro-quinoline-2-carbonitrile

1-ethyl-6-methoxyquinolin-1-ium iodide

2-phenyl-6-methoxyquinoline

3-benzyl-6-methoxy-quinoline

Refernces

• 1、 Kaslow,Raymond. "-". . p. 1102. Retrieved 1946.
• 2、 Auterhoff et al.. "-". . p. 882,885,887. Retrieved 1977.
• 3、 Fiorio, Jhonatan L.,Rossi, Liane M.. "Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold". . p. 312 - 318. Retrieved 2021/01/29.
• 4、 An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee. "Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents". supporting information. p. 2876 - 2894. Retrieved 2021/02/01.