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Sigma-Aldrich

Potassium tert-butoxide

sublimed grade, 99.99% trace metals basis

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Synonym(s):
Potassium tert-butylate, Potassium t-butoxide
Linear Formula:
(CH3)3COK
CAS Number:
865-47-4
Molecular Weight:
112.21
Beilstein:
3556712
EC Number:
212-740-3
MDL number:
MFCD00012162
UNSPSC Code:
12352300
PubChem Substance ID:
24884165
NACRES:
NA.23

grade

sublimed grade

Quality Level

100

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

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

Application

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

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H228,H252,H260,H314

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 2 - Skin Corr. 1A - Water-react 1

Supplementary Hazards

EUH014

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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)
Einav Amit et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(57), 13046-13052 (2020-04-29)
N-heterocyclic carbenes (NHCs) have emerged as a unique molecular platform for the formation of self-assembled monolayers (SAMs) on various surfaces. However, active carbene formation requires deprotonation of imidazolium salt precursors, which is mostly facilitated by exposure of the salt to
E Crespo-Corral et al.
Journal of chromatography. A, 1209(1-2), 22-28 (2008-10-01)
The usefulness of the potassium tert-butoxide/dimethyl sulphoxide/ethyl iodide reaction with carbamate and phenylurea herbicides, and its application to phenoxy acids as a way to prevent hazards and toxicity of the sodium hydride/dimethyl sulphoxide/methyl iodide reaction was studied. Using factorial design
Wei Liu et al.
Chemical communications (Cambridge, England), 49(29), 2983-2985 (2013-03-07)
Simple and cheap alcohols can promote the direct arylation of unactivated arenes with aryl iodides and bromides in the presence of potassium tert-butoxide. This transition-metal-free aromatic C-H transformation offers a cheap and easy practical way to synthesize biaryls under mild
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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