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91-20-3 - Naphthalene, 99+% - A13188 - Alfa Aesar

A13188 Naphthalene, 99+%

CAS Number
91-20-3
Synonyms

Size Price ($) Quantity Availability
250g 18.99
1000g 35.33
5000g 118.45
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Naphthalene, 99+%

MDL
MFCD00001742
EINECS
202-049-5

Chemical Properties

Formula
C10H8
Formula Weight
128.17
Melting point
80-82°
Boiling Point
218°
Flash Point
78°(172°F)
Density
0.963
Refractive Index
1.5821
Solubility
Soluble in benzene, toluene, chloroform, carbon disulfide, ether. Insoluble in water.

Applications

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 C<sub>60</sub> with anthracene.

Notes

Incompatible with strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H351-H400-H410-H302

Flammable solid. Suspected of causing cancer. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects. Harmful if swallowed.

Precautionary Statements: P210-P201-P273-P280-P281-P240-P241-P301+P312-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6370
Beilstein
1421310
Hazard Class
4.1
Packing Group
III
Harmonized Tariff Code
2902.90
TSCA
Yes
RTECS
QJ0525000

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