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328650

Sigma-Aldrich

Potassium tert-butoxide solution

1.0 M in THF

Synonym(s):

Potassium tert-butylate, Potassium-2-methylpropan-2-olate solution

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About This Item

Linear Formula:
(CH3)3COK
CAS Number:
865-47-4
Molecular Weight:
112.21
Beilstein/REAXYS Number:
3556712
MDL number:
MFCD00012162
UNSPSC Code:
12352103
PubChem Substance ID:
24859391
NACRES:
NA.23

form

liquid

Quality Level

200

reaction suitability

core: potassium

concentration

1.0 M in THF

density

0.902 g/mL at 25 °C

SMILES string

[K+].CC(C)(C)[O-]

InChI

1S/C4H9O.K/c1-4(2,3)5;/h1-3H3;/q-1;+1

InChI key

LPNYRYFBWFDTMA-UHFFFAOYSA-N

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General description

Potassium tert-butoxide solution is a strong non nucleophilic base. It is capable of deprotonating carbon and other Bronsted acids. Reagent solutions in tert-BuOh may be prepared by reacting anhydrous alcohol with potassium in nitrogen atmosphere.

Application

Potassium tert-butoxide solution(t-BuOK) can be used:
  • As a catalyst for the interesterification of rapeseed oil with methyl acetate.
  • To promote Sommelet–Hauser rearrangements of N-benzylic amino acid-derived ammonium ylides under mild conditions.
  • As a metal-organic precursor in the synthesis of KNbO3 ferroelectric films by the chemical vapor deposition method.
  • To prepare 3-potassiooxamethylpyridine catalyst.
  • As a strong alkoxide base reagent.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A - STOT SE 3

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 1

flash_point_f

-2.2 °F - closed cup

flash_point_c

-19 °C - closed cup

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One-step methodology for the synthesis of FA picolinyl esters from intact lipids.
Destaillats F and Angers P
Journal of the American Oil Chemists' Society, 79(3), 253-256 (2002)
Hajime Ito et al.
Chemical communications (Cambridge, England), 48(64), 8006-8008 (2012-07-10)
The regio- and diastereoselective silaboration of aromatic alkenes with a silylboron compound proceeds in the presence of a catalytic amount of potassium tert-butoxide, providing a complementary method to the corresponding transition metal-catalyzed reactions.
Aurélie Mallinger et al.
The Journal of organic chemistry, 74(3), 1124-1129 (2008-12-24)
3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps
Scott E Denmark et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(19), 4954-4963 (2006-05-04)
This paper chronicles the conceptual development, proof of principle experiments, and recent advances in the palladium-catalyzed cross-coupling reactions of the conjugate bases of organosilanols. The discovery that led to the design and refinement of this process represents a classical illustration
Subhadip De et al.
Organic letters, 14(17), 4466-4469 (2012-08-16)
A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of
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