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:

99%, ^*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

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

methyl 2-{[4-(quinolin-2-ylmethoxy)phenyl]sulfanyl}benzoate

Refernces

• 1、 Li, Zi-Hao,Fiser, Béla,Jiang, Biao-Lin,Li, Jian-Wei,Xu, Bao-Hua,Zhang, Suo-Jiang. "N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide". supporting information. p. 3403 - 3408. Retrieved 2019/04/01.
• 2、 Xie, Yuanyuan,Li, Lehuan. "Microwave-assisted α-halogenation of 2-methylquinolines with tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane)". supporting information. p. 3892 - 3895. Retrieved 2014/07/08.