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n-Butylsodium

From Wikipedia, the free encyclopedia
n-Butylsodium
Names
Preferred IUPAC name
Butylsodium
Other names
1-Sodiobutane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H9.Na/c1-3-4-2;/h1,3-4H2,2H3;
    Key: IRDQNLLVRXMERV-UHFFFAOYSA-N
  • CCC[CH2].[Na]
Properties
C4H9Na
Molar mass80.106 g·mol−1
Appearancewhite solid[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
Related compounds
Related compounds
n-Butylpotassiumn-Butyllithium
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

n-Butylsodium CH3CH2CH2CH2Na is anorganometallic compound with the idealized formula NaC4H9. Like other simpleorganosodium compounds, it is polymeric and highly basic.[2] In contrast ton-butyllithium,n-butylsodium is only of specialized academic interest.

Preparation

[edit]

n-Butylsodium is prepared fromn-butyllithium andt-butoxysodium.[2]

Properties

[edit]

Inn-Butylsodium, the Na-C bond has ionic character, with a negative charge on the end carbon atom.n-Butylsodium is insoluble in saturated hydrocarbons. It reacts with unsaturated hydrocarbons.[3] Soluble adducts are produced with Lewis bases such astetramethylethylenediamine ortetrahydrofuran.[2]

Reactions

[edit]

n-Butylsodium reacts withalkylbenzene orallylbenzene compounds to give new organosodium compounds. Withtoluene the major product isbenzylsodium.[4]

n-Butylsodium reacts with1-bromonaphthalene to make 1-sodiumnapthalene and1-bromobutane,[5] but there are few suchmetathesis reactions.[6]

References

[edit]
  1. ^Martinez-Martinez, A. J.; Kennedy, A. R.; Mulvey, R. E.; O'Hara, C. T. (13 November 2014)."Supplementary Material for Directed ortho-meta'- and meta-meta'-dimetalations: A template base approach to deprotonation".Science.346 (6211):834–837.Bibcode:2014Sci...346..834M.doi:10.1126/science.1259662.PMID 25395533.S2CID 206561570.
  2. ^abcSchade, Christian; Bauer, Walter; Von Ragué Schleyer, Paul (November 1985). "n-Butylsodium: The preparation, properties and NMR spectra of a hydrocarbon- and tetrahydrofuran-soluble reagent".Journal of Organometallic Chemistry.295 (3):c25–c28.doi:10.1016/0022-328X(85)80326-0.
  3. ^Coates, G. E. (2012).Principles of Organometallic Chemistry. Springer Science & Business Media. p. 50.ISBN 9789401096812.
  4. ^Broaddus, C. D. (September 1966). "Metalation of Toluene. The Question of Kinetic vs. Thermodynamic Control".Journal of the American Chemical Society.88 (18):4174–4178.doi:10.1021/ja00970a012.
  5. ^Gilman, Henry; Moore, Fred W.; Baine, Ogden (September 1941). "Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them".Journal of the American Chemical Society.63 (9):2479–2482.doi:10.1021/ja01854a046.
  6. ^Schlosser, M. (April 1964)."Organosodium and Organopotassium Compounds Part I: Properties and Reactions"(PDF).Angewandte Chemie International Edition in English.3 (4):287–306.doi:10.1002/anie.196402871.
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