254-60-4

Basic information

• Product Name: 1,8-NAPHTHYRIDINE
• Synonyms: 1,8-DIAZANAPHTHALENE;1,8-NAPHTHYRIDINE;PYRIDO[2,3-B]PYRIDINE;1,8-Pyridopyridine;1,8-Naphthyridine(6CI,7CI,8CI,9CI);1,8-NAPHTHYRIDINE 98+%;1,8-Diazanapthalene;1,8-Diazanaphthalene Pyrido[2,3-b]pyridine
• CAS NO: 254-60-4
• Molecular Formula: C₈H₆N₂
• Molecular Weight: 130.15
• Product Categories: PYRIDINE
• Mol File: 254-60-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 99.8-99.9°C
• Boiling Point: 248.9 °C at 760 mmHg
• Flash Point: 107.8 °C
• Appearance: /
• Density: 1.183 g/cm³
• Vapor Pressure: 0.0374mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.55±0.10(Predicted)
• CAS DataBase Reference: 1,8-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-NAPHTHYRIDINE(254-60-4)
• EPA Substance Registry System: 1,8-NAPHTHYRIDINE(254-60-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 254-60-4(Hazardous Substances Data)

Usage

Description

1,8-Naphthyridine, also known as napy, 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

Used in Pharmaceutical Industry:
1,8-Naphthyridine is used as a monodentate and bidentate ligand in the development of pharmaceutical compounds. Its ability to resemble the behavior of carboxylate ligands makes it a valuable component in the synthesis of various drugs.
Used in Antibacterial Applications:
1,8-Naphthyridine derivatives, such as enoxacin, nalidixic acid, and trovafloxacin, are used as antibacterial agents. They exhibit properties related to the fluoroquinolones, making them effective against a range of bacterial infections.

Purification Methods

Purify 1,8-naphthyridine through an Al2O3 column and elute with toluene and pet ether, evaporate the eluate, crystallise the residue from pet ether (b 60-80o), and sublime it at 80o/13mm. The picrate [15936-16-0] has m 207-208o (from EtOH), and the methiodide has m 180-181o (from EtOH). [Hawes & Wibberley J Chem Soc (C) 1564 1967, UV: Armarego Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 134 1971, Beilstein 23 II 178, 23 III/IV 1237.]

InChI:InChI=1/C8H6N2/c1-3-7-4-2-6-10-8(7)9-5-1/h1-6H

Upstream product

• 37960-59-1 1-methyl-1,8-naphthyridinium iodide 
• 504-29-0 2-aminopyridine 
• 86847-59-8 2-(pivaloylamino)pyridine 
• 927-63-9 3-dimethylaminoacrolein 
• 107-02-8 acrolein 
• 50-00-0 formaldehyd 
• 102000-72-6 3-vinylpyridin-2-amine 
• 7521-41-7 2-Aminonicotinaldehyde 
• 75-07-0 acetaldehyde 
• 815-68-9 3-acetylpentane-2,4-dione 
• 927-63-9 (E)-3-(dimethylamino)acrolein 
• 56-81-5 glycerol 

Downstream Products

• 65958-04-5 1-benzoyl-2-indol-3-yl-1,2-dihydro-[1,8]naphthyridine 
• 777862-18-7 cis-[Pt(C₆F₅)2(1,8-naphthyridine)] 
• 819051-88-2 dichloro(1,8-naphthyridine)bis(triphenylphosphine)ruthenium 
• 184244-61-9 [NBu₄][Pt(pentafluorophenyl)3(1,8-naphthrydine)] 
• 777862-19-8 cis-[Pt(C₆F₅)2(CO)(1,8-naphthyridine)] 
• 69110-33-4 2,2'-bi(1,8-naphthyridine) 
• 963-80-4 4,4'-biquinazolinyl 
• 27739-37-3 2,2'-bis(quinoxaline) 
• 1610356-32-5 2-(1,8-naphthyridine-2-yl)quinoxaline 
• 15936-02-4 2-phenyl-1,8-naphthyridine 

Relevant articles and documents

Metal-free stereoselective annulation of quinolines with trifluoroacetylacetylenes and water: An access to fluorinated oxazinoquinolines

Metal-free reaction between quinolines, aryltrifluoroacetylacetylenes and water at -18 °C-rt in MeCN resulted in stereoselective assembly of trifluoromethylated oxazinoquinolines with up to 99% yield that was essentially in contrast to a similar reaction with pyridines. The annulation proceeded via the 1,3-dipolar adducts of quinolines with trifluoroacetylacetylenes followed by intramolecular cyclization involving the trifluoroacetyl group and a molecule of water.

Crystal Structure of 1,8-Naphthyridinium-(1)-tetraphenylborate - Flattening of a Distorted Molecular Skeleton by Protonation (Short Comm.)

Contrary to the usual pyramidalization of nitrogen electron pair centers, the spatially distorted molecular skeleton of 1,8-naphthyridin is planarized upon protonation.

Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier

A general catalytic hydrogen transfer-mediated α-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl α-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to afford novel α-functionalized tetrahydro 1,8-naphthyridines, a class of synthetically useful building blocks and potential candidates for the discovery of therapeutic and bio-active products. The utilization of THQs as inactive hydrogen donors (HDs) appears to be a key strategy to overcome the over-hydrogenation barrier and address the chemoselectivity issue. The developed chemistry features operational simplicity, readily available catalyst and good functional group tolerance, and offers a significant basis for further development of new protocols to directly transform or functionalize inert N-heterocycles.

Selective synthesis of nitrogen bi-heteroarenes by a hydrogen transfer-mediated direct α,β-coupling reaction

By an external hydrogen transfer-mediated activation mode, we herein demonstrate a new palladium-catalyzed direct α,β-coupling of different types of N-heteroarenes. Such a selective coupling reaction proceeds with the advantages of operational simplicity,