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Naphthalene is formerly important in dyestuff manufacture. It acts as a precursor to phthalic anhydride. Naphthalene is used in the manufacturing of phthalic anhydride, naphthalene sulfonic acids and hydrogenated naphthalenes such as 1,2,3,4-tetrahydronaphthalene, which is used as a precursor for various dyestuffs, pigments, rubber processing chemicals and in pharmaceuticals. Its molten form is used as solvent replacing the high- boiling solvents like dichlorobenzene, nitrobenzene and durene. It is involved as reaction medium for in the Diels-Alder reaction between C60 with anthracene.
Reacts with Na metal in 1,2-dimethoxyethane to give Na naphthalenide. This radical anion is a powerful-electron donor, e.g. in reductive dehalogenation of vic-dihalides: J. Chem. Soc., Chem. Commun., 78 (1969), and in reductive cleavage of tosylates to alcohols: J. Am. Chem. Soc., 88, 1581 (1966).
Li naphthalenide is a useful, non-nucleophilic reagent for the conversion of carboxylic acids to their dianions in cases where LDA could interfere: J. Org. Chem., 45, 1106 (1980). Similarly, has been found preferable to LDA in the lithiation of allylic nitriles: Synthesis, 358 (1981).
Carboxylic acids react with alkyl, alkenyl or aryl chlorides in the presence of Li metal and a catalytic amount of naphthalene in THF to give ketones in fair to good yields: J. Org. Chem., 61, 6058 (1996).
Hwang, Y. J.; Earmme, T.; Courtright, B. A.; Eberle, F. N.; Jenekhe, S. A. n-Type Semiconducting Naphthalene Diimide-Perylene Diimide Copolymers: Controlling Crystallinity, Blend Morphology, and Compatibility Toward High-Performance All-Polymer Solar Cells. J. Am. Chem. Soc. 2015, 137 (13), 4424-4434.
Attah, I. K.; Platt, S. P.; Meot-Ner, M.; El-Shall, M. S.; Peverati, R.; Head-Gordon, M. What Is the Structure of the Naphthalene-Benzene Heterodimer Radical Cation? Binding Energy, Charge Delocalization, and Unexpected Charge-Transfer Interaction in Stacked Dimer and Trimer Radical Cations. J. Phys. Chem. Lett. 2015, 6 (7), 1111-1118.
Hazard Statements: H228-H302-H350
Flammable solid. Harmful if swallowed. May cause cancer.
Precautionary Statements: P201-P202-P210-P240-P241-P260-P264b-P270-P271-P281-P301+P312-P304+P340-P308+P313-P330-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF exposed or concerned: Get medical advice/attention. Rinse mouth. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant