254-79-5

Basic information

• Product Name: 1,5-NAPHTHYRIDINE
• Synonyms: 1,5-NAPHTHYRIDINE;1,5-DIAZANAPHTHALENE;PYRIDO[1,5-B]PYRIDINE;1,5-Pyridopyridine;1,5-Naphthyridine(6CI,8CI,9CI);Pyrido[3,2-b]pyridine;1,5-Diazanaphthalene Pyrido[1,5-b]pyridine;1,5-Naphthyridine, 97+%
• CAS NO: 254-79-5
• Molecular Formula: C₈H₆N₂
• Molecular Weight: 130.15
• Product Categories: PYRIDINE;N-Containing;Heterocyclic Building Blocks;Others;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Pyridine series
• Mol File: 254-79-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 74°C
• Boiling Point: 152 °C / 54mmHg
• Flash Point: 107.8 °C
• Appearance: Off-white/Solid
• Density: 1.25
• Vapor Pressure: 0.0374mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.90±0.10(Predicted)
• CAS DataBase Reference: 1,5-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-NAPHTHYRIDINE(254-79-5)
• EPA Substance Registry System: 1,5-NAPHTHYRIDINE(254-79-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• WGK Germany: 3
• Hazardous Substances Data: 254-79-5(Hazardous Substances Data)

Usage

Chemical Properties

off-whtie solid

Purification Methods

Purify 1,5-naphthyridine by repeated sublimation. The picrate crystallises from EtOH with m 200o(dec). [UV: Armarego Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 133 1971, Beilstein 23 II 178, 23 III/IV 1235.]

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

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 56-81-5 glycerol 
• 198549-12-1 4-(2-phenyl-1H-imidazol-1-yl)butanenitrile 
• 198549-21-2 3-(3-(2-phenylimidazol-1-yl)propyl)-1,2,4-triazine 
• 791856-59-2 4-(2-phenylimidazol-1-yl)thiobutyramide 

Downstream Products

• 27305-48-2 1,5-naphthyridine N-⁽¹⁾-oxide 
• 27305-49-3 1,5-naphthyridine 1,5-dioxide 
• 17965-80-9 2-amino-1,5-naphthyridine 
• 13993-61-8 1.1,2,3,4-tetrahydro-1,5-naphthyridine 
• 933687-81-1 decahydro-1,5-naphthyridine 
• 17965-72-9 3,7-dibromo-1,5-naphthyridine 
• 17965-71-8 3-bromo-1,5-naphthyridine 
• 1219022-46-4 6-bromo-1,2,3,4-tetrahydro-1,5-naphthyridine 
• 52831-33-1 ortho -2 ethyl, benzanilide 
• 108958-67-4 [2-(1H-Indol-3-yl)-2H-[1,5]naphthyridin-1-yl]-phenyl-methanone 
• 69110-33-4 2,2'-bi(1,8-naphthyridine) 

Relevant articles and documents

New Tricks by Old Anions: Hydrogen Bonded Hexacyanoferrous Anionic Networks

Hexacyanoferrates are well-known to form metal?organic frameworks by coordination to metal atoms or acting as hydrogen bond acceptors. In this paper we report a new type of hexacyanoferrate self-assembly, based on direct hydrogen bonding of partially protonated hexacyanoferrate anions. By preparing a series of 15 hexacyanoferrates with various organic bases, we have found that protonated hexacyanoferrates (present in 10 structures) readily form chains (two structures), two-dimensional (four structures), or three-dimensional networks (four structures), whereby the dimensionality of the network generally increases with the protonation degree of the hexacyanoferrates. The exact mode of the self-assembly, including the network type, depends on fine interplay of the pKa value of the base, its steric properties, and the stoichiometry of the formed solid.

Electrochemical investigation of structurally varied azinium scaffolds

Inspired by the successful utilization of aziniums as anolytes in redox-flow batteries, we have designed and prepared a systematically extended series of (di)azinium compounds based on pyrazine, bipyridine, 1,5-naphthyridine, 3,8-phenanthroline, (E)-4,4′-

Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)

A set of successive regioselective metalations and functionalizations of the 1,5-naphthyridine scaffold are described. A combination of Zn-, Mg-, and Li-TMP (TMP=2,2,6,6-tetramethylpiperidyl) bases and the presence or absence of a Lewis acid (BF3?OEt2) allows the introduction of up to three substituents to the 1,5-naphthyridine core. Also, a novel “halogen dance” reaction was discovered upon metalation of an 8-iodo-2,4-trifunctionalized 1,5-naphthyridine allowing a fourth regioselective functionalization. Additionally, reactions leading to key 1,5-naphthyridines for the preparation of OLED materials and a potential antibacterial agent were performed.