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Merck
CN

328650

Sigma-Aldrich

Potassium tert-butoxide solution

1.0 M in THF

Synonym(s):

Potassium tert-butylate, Potassium-2-methylpropan-2-olate solution

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About This Item

Linear Formula:
(CH3)3COK
CAS Number:
865-47-4
Molecular Weight:
112.21
Beilstein:
3556712
MDL number:
MFCD00012162
UNSPSC Code:
12352103
PubChem Substance ID:
24859391
NACRES:
NA.23

Key Documents

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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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

-2.2 °F - closed cup

Flash Point(C)

-19 °C - closed cup

Regulatory Information

危险化学品

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBS0580
SHBR2381
SHBP1951
SHBN7231
SHBN2787

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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
Yong Guo et al.
Organic & biomolecular chemistry, 7(8), 1716-1722 (2009-04-04)
Alpha-fluoro-alpha-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either alpha-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an alpha-fluoroketone requires a strong base, such as potassium tert-butoxide, and under these conditions the presence of
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
Astrid Beyer et al.
Organic letters, 14(15), 3948-3951 (2012-07-17)
Potassium tert-butoxide-mediated intramolecular α-arylations of fluoro- and chloro-substituted anilides provide oxindoles in DMF at 80 °C. In this manner, diversely substituted products have been obtained in moderate to high yields.
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