1,8-Naphthyridine

1,8-Naphthyridine
Names
	Preferred IUPAC name 1,8-Naphthyridine
Identifiers
CAS Number	254-60-4;
3D model (JSmol)	Interactive image;
Beilstein Reference	109347
ChEBI	CHEBI:36628;
ChEMBL	ChEMBL261758;
ChemSpider	119846;
ECHA InfoCard	100.201.052
EC Number	675-799-8;
Gmelin Reference	27124
PubChem CID	136069;
UNII	043R04VL4M;
CompTox Dashboard (EPA)	DTXSID40180052;
	InChI InChI=1S/C8H6N2/c1-3-7-4-2-6-10-8(7)9-5-1/h1-6H Key: FLBAYUMRQUHISI-UHFFFAOYSA-N;
	SMILES C1=CC2=C(N=C1)N=CC=C2;
Properties
Chemical formula	C8H6N2
Molar mass	130.150 g·mol−1
Appearance	yellow solid
Density	1.359 g/cm3
Melting point	98–99 °C (208–210 °F; 371–372 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[2]^[3] Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones.^[4]

Coordination chemistry

With flanking nitrogen centers, 1,8-naphthyridine serves as a binucleating ligand in coordination chemistry.^[5]^[6]

References

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Litvinov, Victor P.; Roman, Sergey V.; Dyachenko, Vladimir D. (2000). "Naphthyridines. Structure, Physicochemical Properties and General Methods of Synthesis". Russian Chemical Reviews. 69 (3): 201–220. Bibcode:2000RuCRv..69..201L. doi:10.1070/RC2000v069n03ABEH000553. S2CID 250827396.
^ Dapporto, P.; Ghilardi, C. A.; Mealli, C.; Orlandini, A.; Pacinotti, S. (1984). "Low-Temperature (163 K) Structure of 1,8-Naphthyridine, C₈H₆N₂". Acta Crystallographica Section C Crystal Structure Communications. 40 (5): 891–894. Bibcode:1984AcCrC..40..891D. doi:10.1107/S0108270184006144.
^ V. P. Litvinov (2006). Advances in the Chemistry of Naphthyridines. Advances in Heterocyclic Chemistry. Vol. 91. pp. 189–300. doi:10.1016/S0065-2725(06)91004-6. ISBN 9780120207916.
^ Hua, Shao-An; Liu, Isiah Po-Chun; Hasanov, Hasan; Huang, Gin-Chen; Ismayilov, Rayyat Huseyn; Chiu, Chien-Lan; Yeh, Chen-Yu; Lee, Gene-Hsiang; Peng, Shie-Ming (2010). "Probing the electronic communication of linear heptanickel and nonanickel string complexes by utilizing two redox-active [Ni2(napy)4]3+ moieties". Dalton Transactions. 39 (16): 3890–6. doi:10.1039/b923125k. PMID 20372713.
^ Bera, Jitendra K.; Sadhukhan, Nabanita; Majumdar, Moumita (2009). "1,8-Naphthyridine Revisited: Applications in Dimetal Chemistry". European Journal of Inorganic Chemistry. 2009 (27): 4023–4038. doi:10.1002/ejic.200900312.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[2] Litvinov, Victor P.; Roman, Sergey V.; Dyachenko, Vladimir D. (2000). "Naphthyridines. Structure, Physicochemical Properties and General Methods of Synthesis". Russian Chemical Reviews. 69 (3): 201–220. Bibcode:2000RuCRv..69..201L. doi:10.1070/RC2000v069n03ABEH000553. S2CID 250827396.

[3] Dapporto, P.; Ghilardi, C. A.; Mealli, C.; Orlandini, A.; Pacinotti, S. (1984). "Low-Temperature (163 K) Structure of 1,8-Naphthyridine, C₈H₆N₂". Acta Crystallographica Section C Crystal Structure Communications. 40 (5): 891–894. Bibcode:1984AcCrC..40..891D. doi:10.1107/S0108270184006144.

[4] V. P. Litvinov (2006). Advances in the Chemistry of Naphthyridines. Advances in Heterocyclic Chemistry. Vol. 91. pp. 189–300. doi:10.1016/S0065-2725(06)91004-6. ISBN 9780120207916.

[5] Hua, Shao-An; Liu, Isiah Po-Chun; Hasanov, Hasan; Huang, Gin-Chen; Ismayilov, Rayyat Huseyn; Chiu, Chien-Lan; Yeh, Chen-Yu; Lee, Gene-Hsiang; Peng, Shie-Ming (2010). "Probing the electronic communication of linear heptanickel and nonanickel string complexes by utilizing two redox-active [Ni2(napy)4]3+ moieties". Dalton Transactions. 39 (16): 3890–6. doi:10.1039/b923125k. PMID 20372713.

[6] Bera, Jitendra K.; Sadhukhan, Nabanita; Majumdar, Moumita (2009). "1,8-Naphthyridine Revisited: Applications in Dimetal Chemistry". European Journal of Inorganic Chemistry. 2009 (27): 4023–4038. doi:10.1002/ejic.200900312.

[2]

[3]

[4]

[1]

[5]

[6]

Names

Preferred IUPAC name 1,8-Naphthyridine^[1]
Identifiers
CAS Number	254-60-4
3D model (JSmol)	Interactive image
Beilstein Reference	109347
ChEBI	CHEBI:36628
ChEMBL	ChEMBL261758
ChemSpider	119846
ECHA InfoCard	100.201.052
EC Number	675-799-8
Gmelin Reference	27124
PubChem CID	136069
UNII	043R04VL4M
CompTox Dashboard (EPA)	DTXSID40180052
InChI InChI=1S/C8H6N2/c1-3-7-4-2-6-10-8(7)9-5-1/h1-6H Key: FLBAYUMRQUHISI-UHFFFAOYSA-N
SMILES C1=CC2=C(N=C1)N=CC=C2
Properties
Chemical formula	C₈H₆N₂
Molar mass	130.150 g·mol⁻¹
Appearance	yellow solid
Density	1.359 g/cm³
Melting point	98–99 °C (208–210 °F; 371–372 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references