1,8-Naphthalic anhydride

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1,8-Naphthalic anhydride
Benzo(de)isochromene-1,3-dione 200.svg
Names
Preferred IUPAC name
1H,3H-Naphtho[1,8-cd]pyran-1,3-dione
Other names
1,8-Naphthalenedicarboxylic acid anhydride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.256 Edit this at Wikidata
EC Number
  • 201-380-2
KEGG
UNII
  • 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
  • C1=CC2=C3C(=C1)C(=O)OC(=O)C3=CC=C2
Properties
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:
GHS07: Exclamation mark
Warning
H315, H317, H319, H335
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).

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]

Derivatives include: Alrestatin,...

References[edit]

  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.