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156671

Sigma-Aldrich

Potassium tert-butoxide

greener alternative

reagent grade, ≥98%

Synonym(s):
Potassium tert-butylate, Potassium t-butoxide
Linear Formula:
(CH3)3COK
CAS Number:
Molecular Weight:
112.21
Beilstein:
3556712
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

vapor pressure

1 mmHg ( 220 °C)

assay

≥98%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

256-258 °C (dec.) (lit.)

greener alternative category

Aligned

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

Used for greener amidation of esters.

tert-Butoxide-Assisted Amidation of Esters under Green Conditions

Potassium tert-butoxide may be used as a base in the intramolecular cyclization of iodo arene to afford benzopyran via microwave method of synthesis.
Potassium tert-butoxide has been used as a strong base in the enantioselective synthesis of amines by transfer hydrogenation of N-(tertbutylsulfinyl)imines.
It can also be used:
  • To synthesize aliphatic and aromatic amides from corresponding esters and amines.
  • As a base in the intramolecular cyclization of aryl ethers, amines, and amides.
  • As a catalyst to prepare styrene derivatives from aryl halides and alkenes by Mizoroki-Heck reaction.

Packaging

2.5 kg in poly bottle
5, 25, 100, 500 g in poly bottle

pictograms

FlameCorrosion

signalword

Danger

Hazard Classifications

Flam. Sol. 1 - Skin Corr. 1A - Water-react. 1

Supplementary Hazards

Storage Class Code

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

WGK Germany

WGK 1

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Mizoroki-Heck-type reaction mediated by potassium tert-butoxide
Shirakawa E, et al.
Angewandte Chemie (International ed. in English), 123(20), 4767-4770 (2011)
tert-Butoxide-assisted amidation of esters under green conditions
Kim Bo Ram, et al.
Synthesis, 44(01), 42-50 (2012)
"Potassium tert-Butoxide Promoted Intramolecular Arylation via a Radical Pathway"
Roman SD, et al.
Organic Letters, 13(12), 3242-3245 (2011)
Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) imines
Guijarro D, et al.
Organic Syntheses (2013)
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...

Protocols

Catalytic Amide Bond Formation Protocol

Information on the Amide bond and the Catalytic Amide Bond Formation Protocol. Amidation of amines and alcohols. The amide bond, an important linkage in organic chemistry, is a key functional group in peptides, polymers, and many natural products and pharmaceuticals.

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