Potassium tert-butoxide
| Names | |
|---|---|
| IUPAC name
Potassium 2-methylpropan-2-olate
| |
| Other names
Potassium t-butoxide
Potassium tert-butoxide Potassium tert-butylate | |
| Properties | |
| C4H9OK | |
| Molar mass | 112.21 g/mol |
| Appearance | Colorless to slight yellow solid |
| Odor | Odorless |
| Melting point | 256–258 °C (493–496 °F; 529–531 K) (decomposes) |
| Boiling point | Sublimation begins from 220 °C (428 °F; 493 K) (at 1 mmHg) |
| Reacts | |
| Solubility | Reacts with acids, carboxylic acids, halocarbons Soluble in tert-butanol, THF Slightly soluble in diethyl ether, toluene Poorly soluble in hexane |
| Solubility in diethyl ether | 4.34 g/100 g (25 °C) |
| Solubility in hexane | 0.27 g/100 g (25 °C) |
| Solubility in tert-Butanol | 17.8 g/100 g (25 °C) |
| Solubility in tetrahydrofuran | 25 g/100 g (25 °C) |
| Solubility in toluene | 2.27 g/100 g (25 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
690 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
tert-Butanol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Potassium tert-butoxide is the chemical compound with the formula C4H9OK, sometimes written as (CH3)3CO−K+. It is a strong base (pKa of conjugate acid around 17), very useful in organic reactions.
Contents
Properties
Chemical
Potassium tert-butoxide will readily hydrolyze in water to form tert-butanol and potassium hydroxide.
- (CH3)3COK + H2O → (CH3)3C-OH + KOH
Potassium tert-butoxide reacts exothermically with chloroform.
Physical
Potassium t-butoxide is a colorless solid, which hydrolyzes in water, but has good solubility in organic solvents, like tert-butanol, THF.[1]
Availability
Potassium tert-butoxide is sold by many chemical suppliers.
Preparation
Potassium t-butoxide can be made by carefully adding metallic potassium to tert-butanol.
- (CH3)3C-OH + K → (CH3)3CO−K+ + ½ H2
Purification can be done via sublimation under vacuum.
Projects
- Preparation of metallic potassium
- Strong non-nucleophilic base in organic reactions
- Ignition in contact with chloroform (or dichloromethane)
Handling
Safety
Potassium tert-butoxide is sensitive to water and is corrosive. Wear proper protection when handling the compound.
Storage
Potassium tert-butoxide should be kept in dry air-tight containers, like Schlenk flasks or desiccators.
Disposal
Can be neutralized by adding it in plenty of water, then poured down the drain.
