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Merck

328650

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
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
24859391
MDL number:
MFCD00012162
Beilstein/REAXYS Number:
3556712

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InChI

1S/C4H9O.K/c1-4(2,3)5;/h1-3H3;/q-1;+1

SMILES string

[K+].CC(C)(C)[O-]

InChI key

LPNYRYFBWFDTMA-UHFFFAOYSA-N

form

liquid

reaction suitability

core: potassium

concentration

1.0 M in THF

density

0.902 g/mL at 25 °C

Quality Level

200

Related Categories

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.

signalword

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

supp_hazards

EUH014,EUH019

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3963
SHBS6958
SHBS0580
SHBR2381
SHBP1951

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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
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
View All Related Papers

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