1,8-Naphthalic anhydride

1,8-Naphthalic anhydride
Names
	IUPAC name 3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
	Other names 1,8-Naphthalenedicarboxylic acid anhydride
Identifiers
CAS Number	81-84-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82246;
ChEMBL	ChEMBL316059;
ChemSpider	6438;
ECHA InfoCard	100.001.256
EC Number	201-380-2;
KEGG	C19125;
PubChem CID	6693;
UNII	32RS852X55;
CompTox Dashboard (EPA)	DTXSID4026505 ;
	InChI InChI=1S/C12H6O3/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(14)15-11/h1-6H Key: GRSMWKLPSNHDHA-UHFFFAOYSA-N;
	SMILES C1=CC2=C3C(=C1)C(=O)OC(=O)C3=CC=C2;
Properties
Chemical formula	C12H6O3
Molar mass	198.177 g·mol−1
Appearance	white solid
Melting point	269–276 °C (516–529 °F; 542–549 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H317, H319, H335
GHS precautionary statements	P261, P264, P271, P272, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P403+233, 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-Naphthalic anhydride is an organic compound with the formula C₁₀H₆(C₂O₃). It is one of three isomers of naphthalic anhydride, the other two being the 1,2- and the 2,3-derivatives. The 1,8-isomer is prepared by aerobic oxidation of acenaphthene.[1] 2,6-naphthalenedicarboxylic acid can be prepared from this anhydride.[2] 1,8-Naphthalic anhydride is a precursor to the 4-chloro and 4,5-dichloro derivatives. These chloride groups are susceptible to displacement by amines and alkoxides,[3] giving rise, ultimately, to a large family of naphthalimides, which are used as optical brighteners.[4]

References

Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
Raecke, Bernhard; Schirp, Hubert (1960). "2,6-Naphthalenedicarboxylic acid". Org. Synth. 40: 71. doi:10.15227/orgsyn.040.0071.
Tyman, John; Ghorbanian, Shoreh; Muir, M.; Tychopoulous, Vasiliki; Bruce, Ian; Fisher, Ian (1989). "Improved Nucleophilic Displacements in N-Methyl Pyrrolidinone as a Solvent". Synthetic Communications. 19 (1–2): 179–188. doi:10.1080/00397918908050968.
Haremsa, Sylke (2000). "Naphthalimide Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_059.

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[Ull-1] Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.

[2] Raecke, Bernhard; Schirp, Hubert (1960). "2,6-Naphthalenedicarboxylic acid". Org. Synth. 40: 71. doi:10.15227/orgsyn.040.0071.

[3] Tyman, John; Ghorbanian, Shoreh; Muir, M.; Tychopoulous, Vasiliki; Bruce, Ian; Fisher, Ian (1989). "Improved Nucleophilic Displacements in N-Methyl Pyrrolidinone as a Solvent". Synthetic Communications. 19 (1–2): 179–188. doi:10.1080/00397918908050968.

[4] Haremsa, Sylke (2000). "Naphthalimide Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_059.