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328650

Sigma-Aldrich

Potassium tert-butoxide solution

1.0 M in THF

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Synonym(s):
Potassium tert-butylate, Potassium-2-methylpropan-2-olate solution
Linear Formula:
(CH3)3COK
CAS Number:
865-47-4
Molecular Weight:
112.21
Beilstein:
3556712
MDL number:
MFCD00012162
UNSPSC Code:
12352300
PubChem Substance ID:
24859391
NACRES:
NA.23

form

liquid

Quality Level

200

reaction suitability

core: potassium

concentration

1.0 M in THF

density

0.902 g/mL at 25 °C

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 solution is a strong non nucleophilic base. It is capable of deprotonating carbon and other Bronsted acids. Reagent solutions in tert-BuOh may be prepared by reacting anhydrous alcohol with potassium in nitrogen atmosphere.

Application

Potassium tert-butoxide solution(t-BuOK) can be used:
  • As a catalyst for the interesterification of rapeseed oil with methyl acetate.
  • To promote Sommelet–Hauser rearrangements of N-benzylic amino acid-derived ammonium ylides under mild conditions.
  • As a metal-organic precursor in the synthesis of KNbO3 ferroelectric films by the chemical vapor deposition method.
  • To prepare 3-potassiooxamethylpyridine catalyst.
  • As a strong alkoxide base reagent.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Regulatory Information

危险化学品

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Does the Tetrahydrofuran used to make Product 328650, Potassium tert-butoxide solution, contain a stabilizer?

    Yes, the THF contains about 0.025% butylated hydroxytoluene (BHT) as a stabilizer.

  4. What gloves can I use to work with Product 328650, Potassium tert-butoxide solution?

    We would recommend using Neoprene gloves such as Z402435, Z403407, Z402443, or Z402427.

  5. How do I remove Product 328650, Potassium tert-butoxide solution, from the Sure-Seal bottle?

    The Sure-Seal bottle has a septum held in place with a metal crimp cap. We would recommend removing the product by piercing the septum and withdrawing the liquid through a syringe to reduce the compound's exposure to air and moisture. We offer a line of non-coring syringe needles that are ideal for piercing septa.

  6. How should Product 328650, Potassium tert-butoxide solution, be stored?

    Room temperature storage is acceptable for this solution but we would recommend storing this product under nitrogen. The solution can decompose upon exposure to air or moisture. It also can absorb carbon dioxide from the air which will affect quality of the product.

  7. What is the purity of Product 328650, Potassium tert-butoxide solution?

    We do not perform overall purity testing on this solution. The product is prepared with reagent grade potassium tert-butoxide and then titrated  with hydrochloric acid to define the concentration during the quality control analysis.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

One-step methodology for the synthesis of FA picolinyl esters from intact lipids.
Destaillats F and Angers P
Journal of the American Oil Chemists' Society, 79(3), 253-256 (2002)
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
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
Brian C Anderson et al.
Biomaterials, 23(22), 4345-4352 (2002-09-11)
Several homopolymers and copolymers of 2-(diethylamino)ethyl methacrylate (DEAEM) and poly(ethylene glycol) methyl ether methacrylate (PEGMEM) were synthesized using anionic polymerization initiated by potassium t-butoxide. The polymers were characterized by average molecular weight, polydispersity and monomeric unit composition. A very narrow
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.
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