1,8-Naphthyridine

Base Information

• Chemical Name: 1,8-Naphthyridine
• CAS No.: 254-60-4
• Molecular Formula: C8H6N2
• Molecular Weight: 130.149
• Hs Code.: 2933990090
• European Community (EC) Number: 675-799-8
• UNII: 043R04VL4M
• DSSTox Substance ID: DTXSID40180052
• Nikkaji Number: J100.392E
• Wikipedia: 1,8-Naphthyridine
• Wikidata: Q19961826
• Metabolomics Workbench ID: 55442
• ChEMBL ID: CHEMBL261758
• Mol file: 254-60-4.mol

Synonyms:1,8-Naphthyridine;254-60-4;1,8-Diazanaphthalene;naphthyridine;[1,8]Naphthyridine;1,8-Diazanapthalene;napy;1,8-Pyridopyridine;Pyrido[2,3-b]pyridine;MFCD00059751;UNII-043R04VL4M;CHEBI:36628;043R04VL4M;naphthyridin;1,8-napthyridine;1,8 naphthyridine;SCHEMBL8193;CHEMBL261758;SCHEMBL3713892;SCHEMBL9559247;DTXSID40180052;AKOS005146157;AB02373;AC-9573;CS-W002277;GS-3533;SY021105;AM20070185;FT-0631893;N0464;EN300-94649;J-504060;Q19961826;Z1201618482;W3P

Chemical Property of 1,8-Naphthyridine

Chemical Property:

• Vapor Pressure: 0.0374mmHg at 25°C
• Melting Point: 99.8-99.9 °C
• Refractive Index: 1.653
• Boiling Point: 248.9 °C at 760 mmHg
• PKA: 3.55±0.10(Predicted)
• Flash Point: 107.8 °C
• PSA: 25.78000
• Density: 1.183 g/cm³
• LogP: 1.62980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 130.053098200
• Heavy Atom Count: 10
• Complexity: 102

Purity/Quality:

99% ^*data from raw suppliers

1,8-Naphthyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(N=C1)N=CC=C2
• Description: 1,8-Naphthyridine is an organic compound with the formula C8H6N2. It is the most well-studied of the six isomeric naphthyridines, a subset of diazanaphthalenes with nitrogen in the separate rings. Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones.
• Uses: 1,8-naphthyridine (napy) and its simplest 2-methyl and 2,7-dimethyl derivatives may act as monodentate and bidentate ligands, resembling the behavior of the carboxylate ligands.

Technology Process of 1,8-Naphthyridine

There total 15 articles about 1,8-Naphthyridine 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: 80.0%

(E)-3-(dimethylamino)acrolein (927-63-9,692-32-0) + 2-(pivaloylamino)pyridine (86847-59-8) → 1,8-naphthyridine (254-60-4)

Guidance literature:

2-(pivaloylamino)pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

(E)-3-(dimethylamino)acrolein; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h;

With hydrogenchloride; at 80 - 90 ℃; for 0.75h;

DOI:10.1055/s-2006-926229

Reference yield: 80.0%

2-(pivaloylamino)pyridine (86847-59-8) + 3-dimethylaminoacrolein (927-63-9) → 1,8-naphthyridine (254-60-4)

Guidance literature:

2-(pivaloylamino)pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h; Inert atmosphere;

3-dimethylaminoacrolein; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h; Inert atmosphere;

DOI:10.1002/jhet.4111

Reference yield: 77.0%

→ 1,8-naphthyridine (254-60-4) + 2-(2'-Trifluoromethyl)-1,8-naphthyridine

Guidance literature:

upstream raw materials:

1-methyl-1,8-naphthyridinium iodide

2-aminopyridine

glycerol

(E)-3-(dimethylamino)acrolein

Downstream raw materials:

[2,7-Bis-(1H-indol-3-yl)-7,8-dihydro-2H-[1,8]naphthyridin-1-yl]-phenyl-methanone

1-benzoyl-2-indol-3-yl-1,2-dihydro-[1,8]naphthyridine

1-benzoyl-2-(3-indolyl)-1,2-dihydro-1,8-naphthyridine

1-benzoyl-2,7-bis(2-methyl-3-indolyl)-1,2,7,8-tetrahydro-1,8-naphthyridine

Refernces

• 1、 Margiotta, Nicola,Savino, Salvatore,Gandin, Valentina,Marzano, Christine,Natile, Giovanni. "Monofunctional platinum(II) complexes with potent tumor cell growth inhibitory activity: The effect of a hydrogen-bond donor/acceptor N-heterocyclic ligand". . p. 1161 - 1168. Retrieved 2014.
• 2、 Ucar, Sefa,Dastan, Arif. "One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes". supporting information. p. 4013 - 4022. Retrieved 2020/09/21.
• 3、 Chen, Xiu-Wen,Zhao, He,Chen, Chun-Lian,Jiang, Huan-Feng,Zhang, Min. "Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier". supporting information. p. 14232 - 14236. Retrieved 2017/10/31.