2-Aminoquinoline

Base Information

• Chemical Name: 2-Aminoquinoline
• CAS No.: 580-22-3
• Molecular Formula: C9H8N2
• Molecular Weight: 144.176
• Hs Code.: 29339900
• European Community (EC) Number: 209-458-8
• NSC Number: 58387,57739
• UNII: GR9M8HW75Z
• DSSTox Substance ID: DTXSID2060381
• Nikkaji Number: J54.277F
• Wikidata: Q209310
• Metabolomics Workbench ID: 46401
• ChEMBL ID: CHEMBL61236
• Mol file: 580-22-3.mol

Synonyms:2-AMINOQUINOLINE;quinolin-2-amine;580-22-3;2-Quinolinamine;Aminoquinoline;Quinolinamine;101772-05-8;Quinoline, 2-amino-;quinolin-2-ylamine;2-amino-quinoline;2-Quinolinylamine;CCRIS 1677;139265-95-5;EINECS 209-458-8;MFCD00038079;NSC 57739;NSC 58387;31135-62-3;BRN 0113163;GR9M8HW75Z;2(1H)-Quinolinimine(9CI);CHEMBL61236;NSC-57739;NSC-58387;5-22-10-00220 (Beilstein Handbook Reference);quinolimine;amino-quinoline;a-Aminoquinoline;2ohl;quinoline-2-amine;2AQ;2-Aminoquinoline 1;2-Quinolinamine, 9CI;2-Aminoquinoline, 97%;UNII-GR9M8HW75Z;SCHEMBL38775;1,2-Dihydroquinolin-2-imine;2-imino-1,2-dihydroquinoline;SCHEMBL1146984;DTXSID2060381;BDBM14322;CHEBI:184668;HMS1719H05;BCP30417;NSC57739;NSC58387;BBL100884;STL554678;AKOS000279069;CS-W007524;HY-W007524;PS-4207;SB67709;1,2-DIHYDRO-2-IMINO-QUINOLINE;2-Aminoquinoline pound>>2-Quinolinamine;NCGC00188269-01;AC-13271;SY019963;LS-141297;A0417;A8247;AM20061864;FT-0632430;EN300-10204;A831703;AC-907/25014242;Q209310;J-400243;Z56347237

Chemical Property of 2-Aminoquinoline

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0.000851mmHg at 25°C
• Melting Point: 125 °C
• Refractive Index: 1.7080 (estimate)
• Boiling Point: 304.9 °C at 760 mmHg
• PKA: 3.43(at 20℃)
• Flash Point: 163.6 °C
• PSA: 38.91000
• Density: 1.21 g/cm³
• LogP: 2.39820
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: soluble in Chloroform,Methanol
• Water Solubility.: soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

2-Aminoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-41-37/38-22
• Safety Statements: 26-36/37/39-22-36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=N2)N
• Uses: 2-Aminoquinoline is a useful research chemical.

Technology Process of 2-Aminoquinoline

There total 74 articles about 2-Aminoquinoline 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: 100.0%

dimethylsulfonium acetyl-N-(2-quinolyl)carbamoylmethylide → 2-aminoquinoline (580-22-3)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 2h;

DOI:10.1248/cpb.28.795

Reference yield: 90.0%

N-<2-(2-cyano-1-hydroxyethyl)phenyl>ethyl carbamate (123197-72-8) → 2-aminoquinoline (580-22-3)

Guidance literature:

With sodium hydroxide; In methanol; water; for 24h; Heating;

DOI:10.1016/0040-4020(89)80047-X

Reference yield: 90.0%

N-(quinolin-2-yl)benzamide (33357-46-9) → 2-aminoquinoline (580-22-3)

Guidance literature:

With sulfuric acid; at 50 ℃; for 24h;

DOI:10.1021/acs.joc.1c00741

upstream raw materials:

quinoline

2-Chloroquinoline

2-hydrazinoquinoline

(E)-3-(2-aminobenzene)acrylonitrile

Downstream raw materials:

N-(quinolin-2-yl)benzamide

3-[2]quinolylamino-2-cyano-acrylic acid ethyl ester

N-[2]quinolyl-N'-phenyl-triazene

[2]quinolyl-picryl-amine

Refernces

Sequential and selective Buchwald-Hartwig amination reactions for the controlled functionalization of 6-bromo-2-chloroquinoline: Synthesis of ligands for the Tec Src homology 3 domain

10.1021/jo801808r

The research focuses on the development of new 6-heterocyclic substituted 2-aminoquinolines using Buchwald-Hartwig amination reactions. These compounds are designed to have increased binding affinity for the Tec Src Homology 3 (SH3) domain, a protein-protein interaction domain that is a valuable target for therapeutic agents. The study explores the selective amination of an aryl bromide in the presence of an activated heteroaryl chloride, optimizing reaction conditions to achieve cross-coupling with various cyclic amines. Key chemicals involved in the research include 6-bromo-2-chloroquinoline as the starting material, palladium catalysts such as Pd(OAc)2, various phosphine ligands like CataCXium A (16), and bases like KOtBu and NaOtBu. The reactions also utilize a range of cyclic amines as coupling partners to introduce different heterocyclic substituents at the 6-position of the quinoline ring. The study further investigates the use of lithium bis(trimethylsilyl)amide (LHMDS) as an ammonia equivalent for the amination process to convert 2-chloroquinolines to 2-aminoquinolines, providing an improved method over traditional approaches. The binding affinity of the synthesized compounds with the Tec SH3 domain is assessed through NMR chemical shift perturbation analysis, revealing that the new ligands exhibit enhanced binding affinities compared to the lead compound, 2-aminoquinoline.

Synthesis of 5-, 6- and 7-substituted-2-aminoquinolines as SH3 domain ligands

10.1039/b504498g

The research aims to develop 2-aminoquinolines as ligands for the Src homology 3 (SH3) domains, which are small protein–protein interaction domains involved in important biological processes and are potential targets for therapeutic agents. The study explores the synthesis of various 2-aminoquinolines with substitutions at the 5-, 6-, and 7-positions of the quinoline ring to investigate their binding affinities to the Tec SH3 domain. The highest affinity ligands identified were 6-substituted compounds, with one 6-substituted-N-benzylated-2-aminoquinoline showing potential additional contacts with the SH3 domain. The study concludes that the 6-position is optimal for developing high-affinity small-molecule ligands for the SH3 domains, while substitutions at the 5- and 7-positions generally did not improve binding affinity.

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