Potassium tert-butoxide

Potassium tert-butoxide

chembox new
ImageFile=Potassium tert-butoxide.pngImageSize=120px
IUPACName=potassium 2-methylpropan-2-olate
OtherNames=
Section1=Chembox Identifiers
CASNo=865-47-4
PubChem=23665647
SMILES=CC(C)(C) [O-] . [K+]
Section2=Chembox Properties
Formula=C4H9KO
MolarMass=112.21196
Appearance=
Density=
MeltingPtC=240
BoilingPtC=
Solubility=
Section3=Chembox Hazards
ExternalMSDS = [http://msds.chem.ox.ac.uk/PO/potassium_t-butoxide.html Oxford MSDS]
EUClass = Harmful (Xn), Corrosive (C)
FlashPt=
Autoignition=

Potassium "tert"-butoxide is a white solid with the chemical formula C4H9OK. It is a strong base, sometimes used in Schlosser's base.

Potassium "tert"-butoxide is commercially available. It may be prepared by refluxing dry "tert"-butanol with potassium metal. [OrgSynth | author = William S. Johnson and William P. Schneider | title = β-Carbethoxy-γ,γ-diphenylvinylacetic acid | collvol = 4 | collvolpages = 132 | prep = cv4p0132 | year = 1963]

The "tert"-butoxide species is itself useful as a strong, non-nucleophilic base in organic chemistry. It is able to abstract acidic protons from the substrate molecule readily, but its steric bulk inhibits the group from participating in nucleophilic addition, such as in a Williamson ether synthesis or an SN2 reaction.

References


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