4-Bromo-5-methoxyquinoline

Base Information

• Chemical Name: 4-Bromo-5-methoxyquinoline
• CAS No.: 643069-46-9
• Molecular Formula: C10H8BrNO
• Molecular Weight: 238.08062
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID70696095
• Wikidata: Q82625529
• Mol file: 643069-46-9.mol

Synonyms:4-bromo-5-methoxyquinoline;643069-46-9;4-BROMO-5-METHOXY-QUINOLINE;Quinoline, 4-bromo-5-methoxy-;SCHEMBL3583657;DTXSID70696095;YVSWTMODPAGYGD-UHFFFAOYSA-N;AMY23519;MFCD09261096;AKOS024260552;SB38102;AS-30516;CS-0012679;FT-0707544;EN300-7383833;A852687

Chemical Property of 4-Bromo-5-methoxyquinoline

Chemical Property:

• PSA: 22.12000
• LogP: 3.00590
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 236.97893
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

98.5% ^*data from raw suppliers

4-Bromo-5-methoxy-quinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=NC=CC(=C21)Br

Technology Process of 4-Bromo-5-methoxyquinoline

There total 2 articles about 4-Bromo-5-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: 85.0%

5-methoxy-1H-quinolin-4-one (643069-43-6) → 4-bromo-5-methoxyquinoline (643069-46-9)

Guidance literature:

With phosphorus tribromide; In DMF (N,N-dimethyl-formamide); for 2h;

Reference yield: 45.0%

5--methoxyquinoline N--oxide (90924-16-6) → 4-bromo-5-methoxyquinoline (643069-46-9) + 2--bromo--5--methoxyquinoline (1421517-81-8)

Guidance literature:

With N,N-dimethyl-formamide; phosphorus(V) oxybromide; In dichloromethane; at 0 - 25 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2016.07.083

Reference yield: 18.0%

4-bromo-5-methoxyquinoline (643069-46-9) + C12H22N2O4 (1229624-43-4,615568-57-5) → C22H29N3O5 (1229624-35-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.03.051

upstream raw materials:

5-methoxy-1H-quinolin-4-one

5--methoxyquinoline N--oxide

Downstream raw materials:

C₂₂H₂₉N₃O₅

Refernces

• 1、 Barfoot, Christopher,Brooks, Gerald,Brown, Pamela,Dabbs, Steven,Davies, David T.,Giordano, Ilaria,Hennessy, Alan,Jones, Graham,Markwell, Roger,Miles, Timothy,Pearson, Neil,Smethurst, Christian A.. "Flexible palladium-catalysed amidation reactions for the synthesis of complex aryl amides". body text. p. 2685 - 2689. Retrieved 2010/06/21.