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Sodium naphthalene information


Sodium naphthalene
Names
Preferred IUPAC name
Sodium naphthalenide
Systematic IUPAC name
Sodium naphthalen-1-ide
Other names
sodium naphthalenide, sodium naphthalide
Identifiers
CAS Number
  • 3481-12-7
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10004279 ☒N
ECHA InfoCard 100.020.420 Edit this at Wikidata
EC Number
  • 222-460-3
PubChem CID
  • 11829632
CompTox Dashboard (EPA)
  • DTXSID50188347 Edit this at Wikidata
InChI
  • 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
SMILES
  • c1ccc2=C[CH][CH-]C=c2c1.[Na+]
Properties
Chemical formula
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

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+.[1]

  1. ^ Connelly, Neil G.; Geiger, William E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774.

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Sodium naphthalene

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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...

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Naphthalene

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host of peri-naphthalene derivatives. With alkali metals, naphthalene forms the dark blue-green radical anion salts such as sodium naphthalene, Na+C10H−...

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Surface treatment of PTFE

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Other Multilayer Circuits". Poly-Etch is a sodium naphthalene complex in tetraglyme, while Fluoro-Etch is a sodium naphthalide complex in diglyme Matheson...

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Sodium

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Some well-known derivatives include sodium cyclopentadienide (NaC5H5) and trityl sodium ((C6H5)3CNa). Sodium naphthalene, Na+[C10H8•]−, a strong reducing...

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Radical anion

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deeply colored. Naphthalene in the form of Lithium naphthalene is obtained from the reaction of naphthalene with lithium. Sodium naphthalene is obtained from...

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Sodium chloride

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Sodium chloride /ˌsoʊdiəm ˈklɔːraɪd/, commonly known as edible salt, is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium...

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Sodium hydroxide

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Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of...

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Organosodium chemistry

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one-electron reduction. With solutions of naphthalene, it forms the deeply coloured radical sodium naphthalene, which is used as a soluble reducing agent:...

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Anionic addition polymerization

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Szwarc elucidated that electron transfer occurred from radical anion sodium naphthalene to styrene. The results in the formation of an organosodium species...

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Lithium naphthalene

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other alkali metals (especially sodium), and with diverse ligands attached to the alkali metal cations. Dilithium naphthalene is also known in the form...

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Sodium compounds

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Some well-known derivatives include sodium cyclopentadienide (NaC5H5) and trityl sodium ((C6H5)3CNa). Sodium naphthalene, Na+[C10H8•]−, a strong reducing...

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Sodium sulfide

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with sodium in anhydrous ammonia, or by sodium in dry THF with a catalytic amount of naphthalene (forming sodium naphthalenide): 2 Na + S → Na2S The sulfide...

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Ionic polymerization

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Meanwhile, group 1 metals such as lithium, sodium, and potassium, and their organic compounds (e.g. sodium naphthalene) serve as effective anionic initiators...

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Tetralin

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of naphthalene. It is a colorless liquid that is used as a hydrogen-donor solvent. Tetralin is produced by the catalytic hydrogenation of naphthalene. Although...

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Polychlorinated biphenyl

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some or all chloride. Also effective are reductants such as sodium or sodium naphthalene. Vitamin B12 has also shown promise. The use of microorganisms...

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Sodium phosphide

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with sodium. In some cases, an electron-transfer agent, such as naphthalene, is used. In such applications, the naphthalene forms the soluble sodium naphthalenide...

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Disodium tetracarbonylferrate

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synthesis use sodium naphthalene or sodium benzophenone ketyls as the reducants: Fe(CO)5 + 2 Na → Na2[Fe(CO)4] + CO When a deficiency of sodium is used, the reduction...

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Sodium cyanide

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Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to...

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Allura Red AC

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diazotized 5-amino-4-methoxy-2-toluenesulfonic acid with 6-hydroxy-2-naphthalene sulfonic acid in an azo coupling reaction. Allura Red AC is a popular...

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Living polymerization

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the anionic polymerization of styrene in THF using sodium naphthalene as an initiator. The naphthalene anion initiates polymerization by reducing styrene...

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Phthalic acid

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Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic...

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Calconcarboxylic acid

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(IUPAC name 3-hydroxy-4-[(2-hydroxy-4-sulfonaphthalen-1-yl)diazenyl]naphthalene-2-carboxylic acid; commonly called Patton and Reeder's Indicator) is...

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Sodium iodide

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Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine. Under standard conditions, it...

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Suramin

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contains six aromatic systems – four benzene rings, sandwiched by a pair of naphthalene moieties – plus four amide functional groups (in addition to the urea)...

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Azulene

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Azulene is an aromatic organic compound and an isomer of naphthalene. Naphthalene is colourless, whereas azulene is dark blue. The compound is named after...

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