2-Chloro-3-(chloromethyl)quinoline

Base Information

• Chemical Name: 2-Chloro-3-(chloromethyl)quinoline
• CAS No.: 90097-52-2
• Molecular Formula: C10H7 Cl2 N
• Molecular Weight: 212.078
• Hs Code.: 2933499090
• European Community (EC) Number: 804-661-3
• DSSTox Substance ID: DTXSID70366246
• Nikkaji Number: J433.650J
• Wikidata: Q72517766
• ChEMBL ID: CHEMBL1406957
• Mol file: 90097-52-2.mol

Synonyms:2-chloro-3-(chloromethyl)quinoline;90097-52-2;2-Chloro-3-chloromethylquinoline;MFCD05865134;SR-01000063853;MLS000772109;SCHEMBL377259;CHEMBL1406957;DTXSID70366246;UOIJHUIOTFDGNA-UHFFFAOYSA-N;HMS2674H10;AMY37897;2-chloranyl-3-(chloromethyl)quinoline;AKOS001121043;AB22936;CS-W015028;AS-19040;SMR000376680;SY019483;C2861;FT-0736000;2-Chloro-3-chloromethylquinoline, AldrichCPR;EN300-12086;A825447;A860905;SR-01000063853-1;SR-01000063853-3;Z57983000

Chemical Property of 2-Chloro-3-(chloromethyl)quinoline

Chemical Property:

• Melting Point: 115.0 to 119.0 °C
• PSA: 12.89000
• LogP: 3.62700
• Storage Temp.: 2-8°C
• Solubility.: soluble in Dimethylformamide
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 210.9955546
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-3-(chloromethyl)quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=N2)Cl)CCl
• Uses: 2-Chloro-3-(chloromethyl)quinoline is used as a reactant in the preparation of irreversible HCV NS5B polymerase inhibitors.

Technology Process of 2-Chloro-3-(chloromethyl)quinoline

There total 13 articles about 2-Chloro-3-(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: 93.0%

2-chloro-3-(hydroxymethyl)quinoline (125917-60-4) → 2-chloro-3-(chloropmethyl)quinoline (90097-52-2)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; Reflux;

DOI:10.1039/c5nj02566d

Reference yield: 59.0%

C9H12ClNO + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-chloro-3-(chloropmethyl)quinoline (90097-52-2)

Guidance literature:

With phosphorus pentachloride; In various solvent(s); at 150 ℃; for 4h; variation of temperatures and solvents; also other methylquinolines as substrates;

Reference yield: 41.0%

2-(3-chloro-1-propynyl)formanilide (606146-03-6) → 2-chloro-3-(chloropmethyl)quinoline (90097-52-2) + 3-(chloromethyl)-2,4-dichloroquinoline

Guidance literature:

With triethylamine; lithium chloride; trichlorophosphate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1021/ol035143f

upstream raw materials:

N,N-dimethyl-formamide

2-(3-chloro-1-propynyl)formanilide

N-formyl-2-iodoaniline

2-(3-hydroxy-1-propynyl)formanilide

Downstream raw materials:

ethyl 6-chloro-1-[(2-chloroquinolin-3-yl)methyl]-2-oxo-4-phenyl-1,2-dihydroquinoline-3-carboxylate

4-chloro-N-(5-([(2-chloroquinolin-3-yl)methyl]thio)-1,3,4-thiadiazol-2-yl)benzamide

5-([(2-chloroquinolin-3-yl)methyl]sulfanyl)-N-(phenylmethylidene)-1,3,4-thiadiazol-2-amine

5-([(2-chloroquinolin-3-yl)methyl]sulfanyl)-N-[-(4-methoxyphenyl)methylidene]-1,3,4-thiadiazol-2-amine

Refernces

• 1、 Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.. "Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents". . . Retrieved 2021/03/01.
• 2、 Dasari, Srinivasa Rao,Tondepu, Subbaiah,Vadali, Lakshmana Rao,Ganivada, Mutyala Naidu,Seelam, Nareshvarma. "RETRACTED ARTICLE: Synthesis, Molecular Properties, and Biological Evaluation of Hybrid 1,2,3-Triazolylpolyaza Heterocyclic Compounds". . p. 195 - 208. Retrieved 2019/01/04.