n-Butylsodium
| Names | |
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| Preferred IUPAC name
Butylsodium | |
| Other names
1-Sodiobutane
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C4H9Na | |
| Molar mass | 80.106 g·mol−1 |
| Appearance | white solid[1] |
| Hazards | |
| GHS labelling: | |
| GHS02: Flammable GHS07: Exclamation mark | |
| Danger | |
| Related compounds | |
Related compounds
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n-Butylpotassium n-Butyllithium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit | edit source]n-Butylsodium is prepared from n-butyllithium and t-butoxysodium.[2]
Properties
[edit | edit source]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
[edit | edit source]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
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