7-Chloroquinoline

Base Information

• Chemical Name: 7-Chloroquinoline
• CAS No.: 612-61-3
• Molecular Formula: C9H6 Cl N
• Molecular Weight: 163.606
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID10334803
• Nikkaji Number: J95.376H
• Wikidata: Q72459283
• ChEMBL ID: CHEMBL4877902
• Mol file: 612-61-3.mol

Synonyms:7-chloroquinoline;612-61-3;Quinoline, 7-chloro-;CHEMBL4877902;MFCD00956370;7-Chloro-quinoline;SCHEMBL317870;7-chloroquinoline, AldrichCPR;AMY5105;DTXSID10334803;BDBM50571375;AKOS015851204;AC-6212;CS-W005984;DS-1019;FS-3122;SB67608;SY021162;C3085;FT-0654074;A26294;EN300-114066;J-519225

Chemical Property of 7-Chloroquinoline

Chemical Property:

• Vapor Pressure: 0.0134mmHg at 25°C
• Melting Point: 31.5°C
• Refractive Index: 1.6108 (estimate)
• Boiling Point: 267.5°C at 760 mmHg
• PKA: 3.36±0.14(Predicted)
• Flash Point: 145.2°C
• PSA: 12.89000
• Density: 1.27g/cm³
• LogP: 2.88820
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 163.0188769
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

7-Chloroquinoline ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C(C=C2)Cl)N=C1
• Uses: Chloroquinolines block antibiotic efflux pumps in antibiotic-resistant Enterobacter aerogenes isolates.

Technology Process of 7-Chloroquinoline

There total 13 articles about 7-Chloroquinoline 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%

4,7-dichloroquinoline (86-98-6,1138471-54-1) → quinoline (91-22-5) + 7-chloroquinoline (612-61-3) + 7-chloro-4-hydroxylquinoline (86-99-7)

Guidance literature:

With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 70 ℃; for 18h; chemoselective reaction;

DOI:10.1016/j.tetlet.2009.06.077

Reference yield: 69.0%

7-chloro-4-iodoquinoline (98591-57-2) → 7-chloroquinoline (612-61-3) + 7-chloro-1,2,3,4-tetrahydroquinoline (90562-35-9)

Guidance literature:

With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate; In ethanol; at 20 ℃; for 48h;

DOI:10.3987/COM-09-S(S)19

Reference yield: 24.0%

3-(2-amino-4-chlorophenyl)-propan-1-ol (1060737-02-1) → 7-chloroquinoline (612-61-3) + 7-chloro-1,2,3,4-tetrahydro-2(1H)-quinolinone (14548-50-6)

Guidance literature:

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 60 ℃; for 24h; Molecular sieve;

DOI:10.1039/c2gc35062a

upstream raw materials:

3-chloro-aniline

glycerol

(2E)-3-(4-chlorophenyl)acrylaldehyde O-methyl oxime

glafenine

Downstream raw materials:

1-benzoyl-7-chloro-1,2-dihydro-quinoline-2-carbonitrile

N,N-dimethylquinolin-7-amine

7-chloro-8-nitroquinoline

quinoline-7-carbonitrile

Refernces

• 1、 Khusnutdinov,Bayguzina,Aminov. "Synthesis of quinolines by iron-catalyzed reaction of anilines with propane-1,3-diol". . p. 2725 - 2727. Retrieved 2016/02/18.
• 2、 Chelucci, Giorgio. "Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis". scheme or table. p. 1562 - 1565. Retrieved 2010/06/14.