6-Methoxyquinoline-4-carbaldehyde

Base Information

• Chemical Name: 6-Methoxyquinoline-4-carbaldehyde
• CAS No.: 4363-94-4
• Molecular Formula: C11H9 N O2
• Molecular Weight: 187.198
• Hs Code.: 2933499090
• European Community (EC) Number: 861-723-2
• NSC Number: 449
• DSSTox Substance ID: DTXSID90277027
• Nikkaji Number: J2.368.425J
• Wikidata: Q82007891
• ChEMBL ID: CHEMBL2008611
• Mol file: 4363-94-4.mol

Synonyms:6-methoxyquinoline-4-carbaldehyde;4363-94-4;6-Methoxyquinoline-4-carboxaldehyde;NSC449;SCHEMBL590873;CHEMBL2008611;DTXSID90277027;NSC 449;NSC-449;6-Methoxy-4-quinolinecarbaldehyde;6-Methoxy-quinoline-4-carbaldehyde;6-METHOXY-3-FORMYLQUINOLINE;MFCD06824393;AKOS006282089;AB30483;DS-2524;CS-0043043;FT-0717399;4-QUINOLINECARBOXALDEHYDE, 6-METHOXY-;A872663

Chemical Property of 6-Methoxyquinoline-4-carbaldehyde

Chemical Property:

• Vapor Pressure: 3.52E-05mmHg at 25°C
• Melting Point: 160 °C
• Boiling Point: 353.7°Cat760mmHg
• PKA: 2.98±0.16(Predicted)
• Flash Point: 167.7°C
• PSA: 39.19000
• Density: 1.227g/cm³
• LogP: 2.05590
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 187.063328530
• Heavy Atom Count: 14
• Complexity: 208

Purity/Quality:

99%, ^*data from raw suppliers

6-Methoxyquinoline-4-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C=O
• Uses: 6-methoxyquinoline-4-carbaldehyde is a useful reactant for the synthesis of tetrahydropyran-based bacterial topoisomerase inhibitors.

Technology Process of 6-Methoxyquinoline-4-carbaldehyde

There total 10 articles about 6-Methoxyquinoline-4-carbaldehyde 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: 86.0%

4-bromo-6-methoxyquinoline (42881-66-3) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-methoxyquinoline-4-carbaldehyde (4363-94-4)

Guidance literature:

4-bromo-6-methoxyquinoline; With n-butyllithium; In diethyl ether; at -78 ℃;

N,N-dimethyl-formamide; In diethyl ether; at -78 ℃; for 3h;

DOI:10.1016/j.ejmech.2012.08.047

Reference yield: 77.0%

6-methoxy-4-methylquinoline (41037-26-7) → 6-methoxyquinoline-4-carbaldehyde (4363-94-4)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; water; at 85 ℃; for 5h;

DOI:10.1016/S0223-5234(00)00178-1

Reference yield: 77.0%

2-(6-methoxyquinolin-4-yl)ethanol (105104-88-9) → 6-methoxyquinoline-4-carbaldehyde (4363-94-4)

Guidance literature:

With iron(II) chloride tetrahydrate; iodine; tert-Butyl iodide; trifluoroacetic acid; In dimethyl sulfoxide; at 85 - 95 ℃; for 10h; Inert atmosphere;

DOI:10.1021/jo2026349

upstream raw materials:

6-methoxy-4-methylquinoline

methanol

citric acid monohydrate

quinine monohydrochloride dihydrate

Refernces

• 1、 Xu, Jincheng,Li, Yang,Ding, Tianling,Guo, Hao. "Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes". supporting information. p. 3114 - 3117. Retrieved 2021/09/03.
• 2、 Surivet, Jean-Philippe,Zumbrunn, Cornelia,Rueedi, Georg,Hubschwerlen, Christian,Bur, Daniel,Bruyère, Thierry,Locher, Hans,Ritz, Daniel,Keck, Wolfgang,Seiler, Peter,Kohl, Christopher,Gauvin, Jean-Christophe,Mirre, Azely,Kaegi, Verena,Dos Santos, Marina,Gaertner, Mika,Delers, Jonathan,Enderlin-Paput, Michel,Boehme, Maria. "Design, synthesis, and characterization of novel tetrahydropyran-based bacterial topoisomerase inhibitors with potent anti-gram-positive activity". supporting information. p. 7396 - 7415. Retrieved 2013/10/21.