N-Butylsodium

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.

n-Butylsodium

Names
Preferred IUPAC name Butylsodium
Other names 1-Sodiobutane
Identifiers
CAS Number	3525-44-8
3D model (JSmol)	Interactive image
ChemSpider	11351318 Y
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[1]
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

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]