2-(Chloromethyl)quinoline

Base Information

• Chemical Name: 2-(Chloromethyl)quinoline
• CAS No.: 4377-41-7
• Molecular Formula: C10H8ClN
• Molecular Weight: 177.633
• Hs Code.: 2933499090
• European Community (EC) Number: 224-479-2
• NSC Number: 158442
• DSSTox Substance ID: DTXSID70195932
• Nikkaji Number: J205.756E
• Wikidata: Q83069009
• Mol file: 4377-41-7.mol

Synonyms:2-(Chloromethyl)quinoline;4377-41-7;2-Chloromethylquinoline;EINECS 224-479-2;2-quinolinylmethyl chloride;chloromethylquinoline;2-Chloromethyquinoline;2-chloromethyiquinoline;2-chloromethyl quinolin;2quinolinylmethylchloride;C(Cl)c1ccc2ccccc2n1;2-chloromethyl-quinoline;2-Chloromethyl quinoline;2-quinolinylmethylchloride;2-chloro methyl quinoline;2- (chloromethyl)quinoline;2-(chloro methyl)quinoline;2-(chloromethyl) quinoline;SCHEMBL498405;Quinoline, 2-(chloromethyl)-;DTXSID70195932;2-(CHLOROMETHYL)-QUINOLINE;BCP22822;MFCD00023999;NSC158442;AKOS015850529;AB01399;AM85771;BCP9000080;NSC 158442;NSC-158442;s11826;AC-27318;AS-77032;J-506330

Chemical Property of 2-(Chloromethyl)quinoline

Chemical Property:

• Melting Point: 56.5-57.5℃
• Boiling Point: 288.8 °C at 760 mmHg
• PKA: 3.48±0.48(Predicted)
• Flash Point: 155.9 °C
• PSA: 12.89000
• Density: 1.229 g/cm³
• LogP: 2.97360
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 177.0345270
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

97% ^*data from raw suppliers

2-(Chloromethyl)quinoline 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=N2)CCl
• General Description: 2-(Chloromethyl)quinoline is a key intermediate used in the synthesis of quinoline-based compounds, such as 5-lipoxygenase inhibitors and leukotriene antagonists. It is prepared from quinaldine via its N-oxide monohydrate, followed by reaction with benzenesulfonyl chloride. 2-(chloromethyl)quinoline serves as a reactive building block for coupling with phenol derivatives, enabling the formation of biologically active molecules with potential therapeutic applications.

Technology Process of 2-(Chloromethyl)quinoline

There total 18 articles about 2-(Chloromethyl)quinoline 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: 78.0%

2-methylquinoline (91-63-4) → 2-Chloromethylquinoline (4377-41-7)

Guidance literature:

With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 80 ℃; for 16h; Time; Sealed tube; Inert atmosphere;

DOI:10.1039/c9ob00216b

Reference yield: 76.0%

quinolin-2-ylmethanol (1780-17-2) → 2-Chloromethylquinoline (4377-41-7)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2013.07.090

Reference yield: 76.0%

2-methylquinoline N-oxide (1076-28-4) → 2-Chloromethylquinoline (4377-41-7)

Guidance literature:

With benzenesulfonyl chloride; In toluene; at 80 ℃; for 2h;

DOI:10.1021/jo00064a043

upstream raw materials:

quinolin-2-ylmethanol

quinolin-2-ylmethylbromide

2-methylquinoline N-oxide

trifluoroborane diethyl ether

Downstream raw materials:

2-(phenylthiomethyl)quinoline

2-[(4-chloro-phenylsulfanyl)-methyl]-quinoline

quinolin-2-ylmethanol

2-(2-quinolinylmethoxy)benzoic acid

Refernces

Synthesis and conformation of 2-[[3-(1- hydroxyhexyl)phenoxy]methyl]quinoline, a 5-lipoxygenase inhibitor and leukotriene antagonist

10.1021/jo00064a043

The study focuses on the synthesis and conformational analysis of a quinoline derivative (1), which is an orally active inhibitor of 5-lipoxygenase and a leukotriene antagonist. The key chemicals involved include 2-(chloromethyl)quinoline (4) and the substituted phenol 12, which are coupled in the final step to form the target compound. The phenol derivative 12 is synthesized from m-hydroxyacetophenone (8) through an aldol condensation with n-butyraldehyde, yielding an intermediate that is subsequently reduced to 12. The synthesis of 2-(chloromethyl)quinoline (4) involves converting quinaldine (2) to its N-oxide monohydrate (3) and then reacting it with benzenesulfonyl chloride. The final coupling of 4 and 12 is performed in DMF with anhydrous potassium carbonate as a base, yielding the desired compound 1 in high purity. The study also includes an X-ray crystallographic analysis and molecular mechanics computations to elucidate the conformation of the synthesized compound, revealing a structure where the quinoline and benzenoid rings are nearly perpendicular, providing insights into its potential therapeutic applications.