4-Amino-7-chloroquinoline

Base Information

• Chemical Name: 4-Amino-7-chloroquinoline
• CAS No.: 1198-40-9
• Molecular Formula: C9H7ClN2
• Molecular Weight: 178.621
• Hs Code.: 29420000
• European Community (EC) Number: 601-638-8
• NSC Number: 13
• UNII: 2SJ6Y866TU
• DSSTox Substance ID: DTXSID00152593
• Nikkaji Number: J80.088K
• Wikidata: Q72434959
• Metabolomics Workbench ID: 71596
• ChEMBL ID: CHEMBL44789
• Mol file: 1198-40-9.mol

Synonyms:7-chloro-4-aminoquinoline

Chemical Property of 4-Amino-7-chloroquinoline

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Melting Point: 150-152.5 °C
• Refractive Index: 1.712
• Boiling Point: 366.843 °C at 760 mmHg
• PKA: 7.49±0.50(Predicted)
• Flash Point: 175.66 °C
• PSA: 38.91000
• Density: 1.363 g/cm³
• LogP: 3.05160
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.0297759
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

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

7-Chloroquinolin-4-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN=C2C=C1Cl)N
• Uses: 7-Chloroquinolin-4-amine is an aminoquinoline that complexes ferriprotoporphyrin IX (Fe(III)PPIX) and inhibits its conversion to β-hematin (hemozoin).

Technology Process of 4-Amino-7-chloroquinoline

There total 20 articles about 4-Amino-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: 99.0%

4,7-dichloroquinoline (86-98-6,1138471-54-1) → 4-amino-7-chloroquinoline (1198-40-9)

Guidance literature:

With ammonium carbonate; phenol; at 110 - 165 ℃;

DOI:10.1021/acsmedchemlett.8b00053

Reference yield: 87.0%

7-chloro-4-hydrazinoquinoline (23834-14-2) → 4-amino-7-chloroquinoline (1198-40-9)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; at 20 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2008.01.128

Reference yield: 86.0%

7-chloro-4-iodoquinoline (98591-57-2) → 4-amino-7-chloroquinoline (1198-40-9)

Guidance literature:

With (2-hydroxyethyl)(methyl)amine; copper(l) iodide; formamide; at 80 ℃; for 2.5h; Reagent/catalyst; Sealed tube;

DOI:10.1039/c4nj00046c

upstream raw materials:

4,7-dichloroquinoline

phenylhydrazine

7-chloro-4-methoxyquinoline

ammonium acetate

Downstream raw materials:

4-chloro-5,6,7,8-tetrahydroquinoline

N-(5,6,7,8-tetrahydroquinolin-4-yl)acetamide

Refernces

• 1、 Elderfield et al.. "-". . p. 1250. Retrieved 1946.
• 2、 Bosak, Anita,Opsenica, Dejan M.,?inko, Goran,Zlatar, Matija,Kovarik, Zrinka. "Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase". . p. 101 - 109. Retrieved 2019.
• 3、 Korotchenko, Vasiliy,Sathunuru, Ramadas,Gerena, Lucia,Caridha, Diana,Li, Qigui,Kreishman-Deitrick, Mara,Smith, Philip L.,Lin, Ai J.. "Antimalarial activity of 4-amidinoquinoline and 10-amidinobenzonaphthyridine derivatives". . p. 3411 - 3431. Retrieved 2015.
• 4、 -. "SMALL MOLECULE INHIBITORS OF AUTOPHAGY AND HISTONE DEACTYLASES AND USES THEREOF". Page/Page column 43-44. . Retrieved 2021/05/07.
• 5、 Konstantinovi?, Jelena,Kiris, Erkan,Kota, Krishna P.,Kugelman-Tonos, Johanny,Videnovi?, Milica,Cazares, Lisa H.,Terzi? Jovanovi?, Nata?a,Verbi?, Tatjana ?.,Andjelkovi?, Boban,Duplantier, Allen J.,Bavari, Sina,?olaja, Bogdan A.. "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". supporting information. p. 1595 - 1608. Retrieved 2018/03/06.