659878

Sigma-Aldrich

Potassium tert-butoxide

sublimed grade, 99.99% trace metals basis

Synonym(s):
Potassium tert-butylate, Potassium t-butoxide
Linear Formula:
(CH3)3COK
CAS Number:
Molecular Weight:
112.21
Beilstein/REAXYS Number:
3556712
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

grade

sublimed grade

Quality Level

vapor pressure

1 mmHg ( 220 °C)

assay

99.99% trace metals basis

form

solid

reaction suitability

core: potassium

mp

256-258 °C (dec.) (lit.)

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

Total impurities: may contain up to 5,000 ppm Sodium
Potassium tert-butoxide is a strong alkoxide base, it can deprotonate carbon and other Brφnsted acids. It is a relatively poor nucleophile.

Application

Mizoroki-Heck-Type reactions are mediated by potassium tert-butoxide. potassium tert-butoxide can commence the anionic polymerization of carbazolyl-substituted oxiranes.

Packaging

5, 25 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH014

RIDADR

UN 3131 8(4.3) / PGI

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Anionic polymerization of carbazolyl-substituted oxiranes initiated by potassium alkalide, potassium tert-butoxide and potassium hydride.
Buika G, et al.
Macromolecular Chemistry and Physics, 196(4), 1287-1293 (1995)
Wen-Sen He et al.
Bioresource technology, 114, 1-5 (2012-04-03)
The effects of solvents with different log P values, and of lipases on the synthesis of water-soluble plant stanol derivatives were investigated. Results showed that conversion in solvents with log P<0.37 was mainly controlled by the hydrophobicity of the solvent...
Chang-Liang Sun et al.
Nature chemistry, 2(12), 1044-1049 (2010-11-26)
The direct functionalization of C-H bonds has drawn the attention of chemists for almost a century. C-H activation has mainly been achieved through four metal-mediated pathways: oxidative addition, electrophilic substitution, σ-bond metathesis and metal-associated carbene/nitrene/oxo insertion. However, the identification of...
Huaiqing Zhao et al.
Chemical communications (Cambridge, England), 49(23), 2323-2325 (2013-02-14)
A macrocyclic aromatic pyridone pentamer was shown to catalyze highly efficient transition-metal-free arylations of unactivated aromatic C-H bonds with aryl iodides and bromides in the presence of potassium tert-butoxide.
Eiji Tayama et al.
Organic & biomolecular chemistry, 6(20), 3673-3680 (2008-10-10)
The Stevens rearrangement of N-allylic alpha-aryl amino acid-derived ammonium salts and the Sommelet-Hauser rearrangement of N-benzylic alpha-alkyl amino acid-derived ammonium salts are shown to proceed with remarkably high levels of diastereoselectivity. The methods presented in this work provide new routes...

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