2-Chloro-3-chloromethyl-6-methoxyquinoline

Base Information

• Chemical Name: 2-Chloro-3-chloromethyl-6-methoxyquinoline
• CAS No.: 948291-11-0
• Molecular Formula: C11H9Cl2NO
• Molecular Weight: 242.105
• DSSTox Substance ID: DTXSID70588981
• Wikidata: Q82482034
• Mol file: 948291-11-0.mol

Synonyms:2-Chloro-3-chloromethyl-6-methoxyquinoline;948291-11-0;2-chloro-3-(chloromethyl)-6-methoxyquinoline;starbld0007815;DTXSID70588981;MFCD09787660;AB51929;EN300-6763053

Chemical Property of 2-Chloro-3-chloromethyl-6-methoxyquinoline

Chemical Property:

• Vapor Pressure: 2.32E-05mmHg at 25°C
• Boiling Point: 370.7°C at 760 mmHg
• Flash Point: 178°C
• PSA: 22.12000
• Density: 1.341g/cm³
• LogP: 3.63560
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 241.0061193
• Heavy Atom Count: 15
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

2-CHLORO-3-CHLOROMETHYL-6-METHOXYQUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=CC(=C(N=C2C=C1)Cl)CCl

Technology Process of 2-Chloro-3-chloromethyl-6-methoxyquinoline

There total 4 articles about 2-Chloro-3-chloromethyl-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: 91.0%

3-(hydroxymethyl)-2-chloro-6-methoxyquinoline (92172-83-3) → 2-chloro-3-(chloromethyl)-6-methoxyquinoline (948291-11-0)

Guidance literature:

With thionyl chloride; In benzene; at 80 ℃;

DOI:10.1016/j.bmcl.2015.01.012

Reference yield:

2-chloro-6-methoxyquinolin-3-carboxaldehyde (73568-29-3) → 2-chloro-3-(chloromethyl)-6-methoxyquinoline (948291-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 4 h / 0 - 30 °C

2: thionyl chloride; pyridine / benzene / 2 h / 0 - 80 °C

With pyridine; sodium tetrahydroborate; thionyl chloride; In ethanol; benzene;

DOI:10.2174/1570180811310040008

Reference yield:

4-methoxy-aniline (104-94-9) → 2-chloro-3-(chloromethyl)-6-methoxyquinoline (948291-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.5 h / 20 °C / Reflux

2.1: trichlorophosphate / 1 h / 0 - 5 °C

2.2: 0 - 80 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

4.1: thionyl chloride / dichloromethane / 6 h / 50 °C

With sodium tetrahydroborate; thionyl chloride; trichlorophosphate; In methanol; dichloromethane; 2.1: |Vilsmeier-Haack Formylation / 2.2: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.bmcl.2021.127855

upstream raw materials:

3-(hydroxymethyl)-2-chloro-6-methoxyquinoline

2-chloro-6-methoxyquinolin-3-carboxaldehyde

4-methoxy-aniline

4-methoxyacetanilide

Downstream raw materials:

C₂₈H₂₀Cl₂N₂O₃

C₂₂H₂₀ClN₅O₃

C₂₁H₁₈Cl₂N₄O₂

C₂₀H₁₆Cl₂N₄O₂