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156671

Sigma-Aldrich

Potassium tert-butoxide

greener alternative

reagent grade, ≥98%

Synonym(s):

Potassium tert-butylate, Potassium t-butoxide

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About This Item

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:
12352303
PubChem Substance ID:
24849626
NACRES:
NA.22
Assay:
≥98%
grade:
reagent grade
form:
solid
Pricing and availability is not currently available.

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.[1]
It can also be used:
  • To synthesize aliphatic and aromatic amides from corresponding esters and amines.[2]
  • As a base in the intramolecular cyclization of aryl ethers, amines, and amides.[3]
  • As a catalyst to prepare styrene derivatives from aryl halides and alkenes by Mizoroki-Heck reaction.[4]

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.[3]

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H228,H252,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2788
MKCX0896
MKCV0306
MKCR0575

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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)
"Potassium tert-Butoxide Promoted Intramolecular Arylation via a Radical Pathway"
Roman SD, et al.
Organic Letters, 13(12), 3242-3245 (2011)
tert-Butoxide-assisted amidation of esters under green conditions
Kim Bo Ram, et al.
Synthesis, 44(01), 42-50 (2012)
Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) imines
Guijarro D, et al.
Organic Syntheses (2013)
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
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How can we see melting point of by MR meter Or is it best we go for DSC

    1 answer

    1. The melting point of item 156671 is 256-258°C, as described in the literature. Due to the higher range, the DSC method would be preferred for this compound.

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