Sodium naphthalene

Sodium naphthalene is an organic salt with the chemical formula Na+[C10H8]−. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a solvate with ligands bound to Na+.

Sodium naphthalene
Names
Preferred IUPAC name
Sodium naphthalenide
Systematic IUPAC name
Sodium naphthalen-1-ide
Other names
sodium naphthalenide, sodium naphthalide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.420
EC Number
  • 222-460-3
  • InChI=1S/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1 N
    Key: NCVIXNVCXNGGBW-UHFFFAOYSA-N N
  • InChI=1/C10H8.Na/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H;/q-1;+1
    Key: NCVIXNVCXNGGBW-UHFFFAOYAJ
  • c1ccc2=C[CH][CH-]C=c2c1.[Na+]
Properties
Na+[C10H8]−
Molar mass 151.164 g·mol−1
Appearance Deep green crystals
Related compounds
Other anions
 Lithium naphthalene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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