Tetrabutylammonium hydroxide

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Tetrabutylammonium hydroxide
Names
Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium hydroxide
Other names
TBAH, TBAOH
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.016.498 Edit this at Wikidata
UNII
  • InChI=1S/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1 checkY
    Key: VDZOOKBUILJEDG-UHFFFAOYSA-M checkY
  • InChI=1/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1
    Key: VDZOOKBUILJEDG-REWHXWOFAE
  • [OH-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
C16H37NO
Molar mass 259.478 g·mol−1
soluble
Solubility soluble in most organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrabutylammonium hydroxide is the

NaOH, Bu4NOH is more soluble in organic solvents.[1]

Preparation and reactions

Solutions of Bu4NOH are usually prepared in situ from butylammonium halides, Bu4NX, for example by reacting them with

1-butene. Solutions of Bu4NOH are typically contaminated with Bu3N for this reason.[1]

Treatment of Bu4NOH with a wide range of acids gives water and the other tetrabutylammonium salts:

Applications

Bu4NOH is a strong base that is used often under

benzylation of amines and generation of dichlorocarbene from chloroform.[1]

Bu4NOH can be

desilylation.[3]

References

  1. ^
    ISBN 0-471-93623-5
    ..
  2. ^ Woodside, A. B.; Huang, Z.; Poulter, C. D. (1993). "Trisammonium Geranyl Diphosphate". Organic Syntheses; Collected Volumes, vol. 8, p. 616.
  3. ^ Kuwajima, I.; Nakamura, E.; Hashimoto, K. (1990). "Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene". Organic Syntheses; Collected Volumes, vol. 7, p. 512.
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