n-Butylsodium

n-Butylsodium
Names
	Preferred IUPAC name Butylsodium
	Other names 1-Sodiobutane
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	11351318 ;
PubChem CID	101040259;
	InChI InChI=1S/C4H9.Na/c1-3-4-2;/h1,3-4H2,2H3; Key: IRDQNLLVRXMERV-UHFFFAOYSA-N;
	SMILES CCC[CH2].[Na];
Properties
Chemical formula	C4H9Na
Molar mass	80.106 g·mol−1
Appearance	white solid
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Related compounds
Related compounds	n-Butylpotassium n-Butyllithium
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

n-Butylsodium CH₃CH₂CH₂CH₂Na is an organometallic compound with the idealized formula NaC₄H₉. Like other simple organosodium compounds, it is polymeric and highly basic.^[2] In contrast to n-butyllithium, n-butylsodium is only of specialized academic interest.

Preparation

n-Butylsodium is prepared from n-butyllithium and t-butoxysodium.^[2]

Properties

In n-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 as tetramethylethylenediamine or tetrahydrofuran.^[2]

Reactions

n-Butylsodium reacts with alkylbenzene or allylbenzene compounds to give new organosodium compounds. With toluene the major product is benzylsodium.^[4]

n-Butylsodium reacts with 1-bromonaphthalene to make 1-sodiumnapthalene and 1-bromobutane,^[5] but there are few such metathesis reactions.^[6]

References

^ 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.
^ a b c Schade, 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.
^ Coates, G. E. (2012). Principles of Organometallic Chemistry. Springer Science & Business Media. p. 50. ISBN 9789401096812.
^ 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.
^ 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.
^ 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.

[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.

[schade-2] Schade, 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.