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Sigma-Aldrich

Potassium tert-butoxide

greener alternative

reagent grade, ≥98%

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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:
24849626
NACRES:
NA.22

grade

reagent grade

Quality Level

200

vapor pressure

1 mmHg ( 220 °C)

Assay

≥98%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

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

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.

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.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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