n-Butylsodium

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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 mass 80.106 g·mol−1
Appearance white solid[1]
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
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).

n-Butylsodium CH3CH2CH2CH2Na is an

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-bromobutane,[5] but there are few such metathesis reactions.[6]

References

  1. S2CID 206561570
    .
  2. ^
    doi:10.1016/0022-328X(85)80326-0
    .
  3. ISBN 9789401096812
    .
  4. doi:10.1021/ja00970a012
    .
  5. doi:10.1021/ja01854a046
    .
  6. doi:10.1002/anie.196402871
    .
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