1,8-Naphthalic anhydride

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]

1,8-Naphthalic anhydride

Names
Preferred IUPAC name 1H,3H-Naphtho[1,8-cd]pyran-1,3-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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335
Precautionary statements	P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, 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

Derivatives include: Alrestatin,...