3-Azidoquinoline

Base Information

• Chemical Name: 3-Azidoquinoline
• CAS No.: 14213-02-6
• Molecular Formula: C9H6N4
• Molecular Weight: 170.173
• DSSTox Substance ID: DTXSID30493042
• Nikkaji Number: J2.707.764A
• Wikidata: Q82339420
• Mol file: 14213-02-6.mol

Synonyms:3-azidoquinoline;14213-02-6;Quinoline, 3-azido-;DTXSID30493042;AKOS006370713;EN300-265516;F1906-0416

Chemical Property of 3-Azidoquinoline

Chemical Property:

• Melting Point: 79-80 °C(Solv: hexane (110-54-3); acetone (67-64-1))
• PSA: 62.64000
• LogP: 2.62936
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 170.059246208
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

3-Azidoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C=N2)N=[N+]=[N-]

Technology Process of 3-Azidoquinoline

There total 2 articles about 3-Azidoquinoline 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%

3-aminoquinoline (580-17-6) → 3-azidoquinoline (14213-02-6)

Guidance literature:

3-aminoquinoline; With hydrogenchloride; sodium nitrite; In water; at 0 - 5 ℃;

With sodium azide; In water; at 0 ℃;

DOI:10.3762/bjoc.7.129

Reference yield:

quinolin-3-ylboronic acid (191162-39-7) → 3-azidoquinoline (14213-02-6)

Guidance literature:

With sodium azide; copper(ll) sulfate pentahydrate; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.111696

Reference yield: 100.0%

3-azidoquinoline (14213-02-6) + 20-deoxy-20-(N-benzyl-N-propargylamino)-5-O-mycaminosyltylonolide → 20-deoxy-20-{N-benzyl-N-[1-(3-quinolyl)-1H-1,2,3-triazol-4-yl]methylamino}-5-O-mycaminosyltylonolide

Guidance literature:

With tetrakis(actonitrile)copper(I) hexafluorophosphate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In methanol; at 20 ℃;

DOI:10.1038/ja.2017.61

upstream raw materials:

3-aminoquinoline

quinolin-3-ylboronic acid

Downstream raw materials:

2-Methyl-oxazolo<4.5-c>-chinolin

3-Amino-2-methoxyquinoline

4-methoxy-[3]quinolylamine

3-aminoquinoline

Refernces

• 1、 Berwanger, Aylin,Empting, Martin,Jakob, Valentin,Kirsch, Philine,Rinkes, Julia,Schulz, Thomas F.,Stein, Saskia C.. "Hit-to-lead optimization of a latency-associated nuclear antigen inhibitor against Kaposi's sarcoma-associated herpesvirus infections". supporting information. . Retrieved 2020/07/07.
• 2、 Jing, Lanlan,Wu, Gaochan,Hao, Xia,Olotu, Fisayo A.,Kang, Dongwei,Chen, Chin Ho,Lee, Kuo-Hsiung,Soliman, Mahmoud E.S.,Liu, Xinyong,Song, Yuning,Zhan, Peng. "Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries". . . Retrieved 2019/09/19.