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702757

Sigma-Aldrich

Potassium tert-pentoxide solution

2 M in THF

Synonym(s):

Potassium tert-amylate, Potassium (2-methyl-2-butoxide), Potassium tert-pentylate

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About This Item

Linear Formula:
CH3CH2C(CH3)2OK
CAS Number:
Molecular Weight:
126.24
Beilstein:
4149025
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

form

liquid

concentration

2 M in THF

density

0.920 g/mL at 25 °C

SMILES string

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

InChI

1S/C5H11O.K/c1-4-5(2,3)6;/h4H2,1-3H3;/q-1;+1

InChI key

ZRLVQFQTCMUIRM-UHFFFAOYSA-N

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General description

Potassiumtert-pentoxide solution is a strong and sterically hindered alkoxide baseprepared by treating oil-free potassium hydride with anhydrous t-pentylalcohol in anhydrous solvent.

Application

Potassium tert-pentoxide solution can be used as a base in the:
  • Wittig reaction of ketoesters with methyltriphenylphosphonium bromide to synthesize alkenes.
  • Palladium-catalyzed Buchwald-Hartwig amination reaction.
It can also be used:
  • To prepare potassium tert-pentoxide-crown ether complexes, which is used as a Lewis base catalyst in Mukaiyama aldol reaction.
  • As an activator for (difluoromethyl)trimethylsilane to generate difluoromethyl-carbanion which reacts with isothiocyanate to synthesize α, α-difluoromethyl thioamide.

Features and Benefits

In the absence of air and moisture, potassium tert-pentoxide solutions in benzene or toluene may be stored in a refrigerator for up to 1 year without significant deterioration.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - Solvent

Flash Point(C)

-17 °C - Solvent

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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