1,8-Naphthyridine
{{Chembox
| ImageFile = 1,8-naphthyridine.svg
| ImageSize = 144
| ImageAlt =
| PIN = 1,8-Naphthyridine{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=212 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 254-60-4
| PubChem = 136069
| UNII = 043R04VL4M
| ChEBI = 36628
| ChEMBL = 261758
| Gmelin = 27124
| EINECS = 675-799-8
| ChemSpiderID = 119846
| DTXSID = DTXSID40180052
| Beilstein = 109347
| StdInChI=1S/C8H6N2/c1-3-7-4-2-6-10-8(7)9-5-1/h1-6H
| StdInChIKey = FLBAYUMRQUHISI-UHFFFAOYSA-N
| SMILES = C1=CC2=C(N=C1)N=CC=C2
}}
|Section2={{Chembox Properties
| C=8|H=6|N=2
| MolarMass =
| Appearance = yellow solid
| Density = 1.359 g/cm3
| MeltingPtC = 98-99
| BoilingPtC =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite journal|doi=10.1070/RC2000v069n03ABEH000553|bibcode=2000RuCRv..69..201L|title=Naphthyridines. Structure, Physicochemical Properties and General Methods of Synthesis|year=2000|last1=Litvinov|first1=Victor P.|last2=Roman|first2=Sergey V.|last3=Dyachenko|first3=Vladimir D.|journal=Russian Chemical Reviews|volume=69|issue=3|pages=201–220|s2cid=250827396 }}{{cite journal|doi = 10.1107/S0108270184006144|title = Low-Temperature (163 K) Structure of 1,8-Naphthyridine, C8H6N2|year = 1984|last1 = Dapporto|first1 = P.|last2 = Ghilardi|first2 = C. A.|last3 = Mealli|first3 = C.|last4 = Orlandini|first4 = A.|last5 = Pacinotti|first5 = S.|journal = Acta Crystallographica Section C Crystal Structure Communications|volume = 40|issue = 5|pages = 891–894| bibcode=1984AcCrC..40..891D }} Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones.{{cite book|series=Advances in Heterocyclic Chemistry
|title=Advances in the Chemistry of Naphthyridines|author=V. P. Litvinov|year=2006|pages=189–300|volume=91|doi=10.1016/S0065-2725(06)91004-6|isbn=9780120207916}}
Coordination chemistry
With flanking nitrogen centers, 1,8-naphthyridine serves as a binucleating ligand in coordination chemistry.{{cite journal|doi=10.1039/b923125k|pmid=20372713|title=Probing the electronic communication of linear heptanickel and nonanickel string complexes by utilizing two redox-active [Ni2(napy)4]3+ moieties|year=2010|last1=Hua|first1=Shao-An|last2=Liu|first2=Isiah Po-Chun|last3=Hasanov|first3=Hasan|last4=Huang|first4=Gin-Chen|last5=Ismayilov|first5=Rayyat Huseyn|last6=Chiu|first6=Chien-Lan|last7=Yeh|first7=Chen-Yu|last8=Lee|first8=Gene-Hsiang|last9=Peng|first9=Shie-Ming|journal=Dalton Transactions|volume=39|issue=16|pages=3890–6}}{{cite journal|doi = 10.1002/ejic.200900312|title = 1,8-Naphthyridine Revisited: Applications in Dimetal Chemistry|year = 2009|last1 = Bera|first1 = Jitendra K.|last2 = Sadhukhan|first2 = Nabanita|last3 = Majumdar|first3 = Moumita|journal = European Journal of Inorganic Chemistry|volume = 2009|issue = 27|pages = 4023–4038}}