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Potassium tert-butoxide

Strong organic alkaline chemical properties reaction Uses preparation Precautions

CAS No.865-47-4
Chemical Name:Potassium tert-butoxide
CBNumber:CB1335932
Molecular Formula:C4H9KO
Formula Weight:112.21
MOL File:865-47-4.mol

Potassium tert-butoxide Property

Melting point 256-258 °C (dec.) (lit.)
Boiling point 275°C
Density 0.910 g/mL at 20 °C
bulk density 500kg/m3
vapor pressure 1 mm Hg ( 220 °C)
Flash point 54 °F
storage temp. Store below +30°C.
solubility Soluble in hexane, toluene, diethyl ether and terahydrofuran.
pka pK1:18(25°C)
form Solution
Specific Gravity 0.902
color White to off-white
PH 13 (5g/l, H2O, 20℃)Hydrolysis
Water Solubility REACTS
Sensitive Moisture Sensitive
Hydrolytic Sensitivity 7: reacts slowly with moisture/water
BRN 3556712
Stability Stable, but reacts violently with water and acids, possibly leading to fire. Incompatible with water, acids, halogenated hydrocarbons, alcohols, strong oxidizing agents, ketones, carbon dioxide.
InChIKey LPNYRYFBWFDTMA-UHFFFAOYSA-N
CAS DataBase Reference 865-47-4(CAS DataBase Reference)
FDA UNII VR838VHE0V
EPA Substance Registry System 2-Methyl-2-propanol, potassium salt (865-47-4)
UNSPSC Code 12352303
NACRES NA.23

Safety

Hazard Codes :F,C,Xi
Risk Statements :11-19-22-34-35-14-20-36/37-37
Safety Statements :16-26-36/37/39-43-45-7/9-8-43A-33-27-29
RIDADR :UN 3274 3/PG 2
WGK Germany :1
F :10-21
Autoignition Temperature :483 °C
Hazard Note :Flammable solid/Corrosive
TSCA :Yes
HazardClass :8
PackingGroup :I
HS Code :29051900

NFPA 704:

	2
3		2
	W

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H228-H260-H314
Precautionary statements P210-P231+P232-P260-P280-P303+P361+P353-P305+P351+P338

Potassium tert-butoxide Price More Price(27)

Brand: Sigma-Aldrich(India)
Product number: 8.43849
Product name : Potassium tert-butylate
Purity: (~ 20% solution in tetrahydrofuran) for synthesis
Packaging: 50ML
Price: ₹8049.99
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.04918
Product name : Potassium tert-butylate
Purity: for synthesis
Packaging: 100G
Price: ₹5570
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.43849
Product name : Potassium tert-butylate
Purity: (~ 20% solution in tetrahydrofuran) for synthesis
Packaging: 250ML
Price: ₹21050
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.04918
Product name : Potassium tert-butylate
Purity: for synthesis
Packaging: 250G
Price: ₹12620.01
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.04918
Product name : Potassium tert-butylate
Purity: for synthesis
Packaging: 2.5KG
Price: ₹19050
Updated: 2022/06/14
Buy: Buy

Potassium tert-butoxide Chemical Properties,Usage,Production

Strong organic alkaline Because of the induction effect of three methyl groups in the (CH3) 3CO-, Potassium tert-butoxide has stronger alkalinity and activity than other potassium alkoxides, thus being a very excellent catalyst. In addition, as a kind of strong alkaline, potassium tert-butoxide is widely used in the organic synthesis of chemical, pharmaceutical, and pesticide such as trans-esterification, condensation, rearrangement, polymerization, loop opening and the production of heavy metal orthoester. It can be used to catalyze the Michael addition reaction, Pinacol rearrangement reaction and Ramberg-Backlund rearrangement reaction. Potassium tert-butoxide is used as a condensing agent, which can be used to catalyze Darzens condensation reaction and Stobbe condensation reaction. It is also the most effective alkaline for traditional akloxide-haloform reaction generating dihalogenated carbene.
chemical properties Potassium tert-butoxide is a strong alkaline condensing agent with its alkalinity is stronger than sodium methoxide and sodium ethoxide. At room temperature, this product is white or white-like solid powder with its chemical formula being (CH3) 3C-O-K, molecular weight being 112.21, density being 0.929, the melting point of 256-258°C and the boiling point being 275°C. It is easy to absorb moisture. It is soluble in tert-butanol with the solution being relative stable, and commonly used in the dehydrohalogenation reaction of halogenated hydrocarbon. Being exposure to air decomposition, it can be decomposed into potassium oxide and tert-butyl alcohol when coming across water.
reaction Potassium tert-butoxide may be used as a base in the intramolecular cyclization of iodo arene to afford benzopyran via microwave method of synthesis.
Potassium tert-butoxide has been used as a strong base in the enantioselective synthesis of amines by transfer hydrogenation of N-(tertbutylsulfinyl)imines.
Take 2, 6, 6-trimethylcyclohexane-2-alkenyl formaldehyde to have reaction with allyl Grignard agent to generate cyclohexenyl butenol, followed by the oxidation under copper-zinc catalyst to generate cyclohexane alkenyl ketene, followed by isomerization in the alkali solution of potassium tert-butoxide, being able to generate Damascenone.

Darzen reaction: aldehydes and ketones, in the presence of alkaline reagents, can have ester-aldol condensation reaction with α-halo acid ester, while having the hydrogen halogen lost, generating α, β-epoxy ester. Common alkaline reagents include sodium ethoxide, sodium amide, sodium metal, potassium tert-butoxide and so on.
Stobbe reaction: aldehydes, ketones and succinate ester, in the presence of alkaline catalysts (such as sodium ethoxide, potassium tert-butoxide, sodium chloride, etc.) have reaction similar to the aldol condensation reaction, generating succinate or its monoester with the methylene replaced by hydrocarbon.
KOtBu: A Privileged Reagent for Electron Transfer Reactions
Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions
Uses Potassium tert-butoxide, as a strong alkaline, is widely used in the condensation, rearrangement and ring opening reaction in organic production in the fields of chemical, pharmaceutical and pesticide.
It can also be used:
To synthesize aliphatic and aromatic amides from corresponding esters and amines.
As a base in the intramolecular cyclization of aryl ethers, amines, and amides.
As a catalyst to prepare styrene derivatives from aryl halides and alkenes by Mizoroki-Heck reaction.
preparation The potassium metal was added to the freshly distilled tert-butanol under nitrogen atmosphere, refluxed to until the potassium was completely melted. Further incubate for 1 hour. The excess amount of t-butyl alcohol was distilled off with the remaining white solid subjecting to vacuum drying under reduced pressure at 180-190 °C for 10 h. Then we can obtain the crystal powder of potassium tert-butanol. It needs to saved be under the nitrogen atmosphere for using. It should be kept away from air & water, or will become pink. The yield, calculated according to potassium, is more than 99%. The chemical reaction equation for the reaction between tert-butyl alcohol and metal potassium for preparation of potassium tert-butoxide is as follows:
Precautions Potassium tert-butoxide has two types, liquid and solid. Usually the liquid industrial product is the tert-butanol solution of tert-butanol potassium with the color of the product being light yellow or milky white, being slightly turbid, in which the content of potassium tert-butoxide being 10% to 12%; the solid product is generally white or white powder in which the potassium tert-butoxide content is 95% to 97%.
Potassium tert-butoxide is organic alkaline corrosion product with strong moisture absorption property. It should be generally sealed for storage, generally stored in a cool, dry, ventilated warehouse. It should be kept away from heat and isolated from fire isolation as well as being protected from sun exposure. Potassium tert-butoxide has a strong corrosive effect on the skin. During the handling and loading process, the operator should wear a protective mask to prevent corrosion and burning by potassium tert-butoxide.
The above information is edited by Tongtong from Chemicalbook.
Chemical Properties white crystalline powder
Uses Potassium tert-butylate is used to catalyzes the Michael addition reaction.
General Description Potassium tert-butoxide is an important kind of organic base with its alkalinity being stronger than potassium hydroxide. It is widely used in the condensation, rearrangement and ring opening reaction in organic production in the fields of chemical, pharmaceutical and pesticide.
Fire Hazard Potassium tert-butoxide is a flammable solid. It ignites on heating. Being very strongly basic, its reactions with acids are highly exothermic. Contact of solid powder with drops of sulfuric acid and vapors of acetic acid caused ignition after an induction period of 0.5 and 3 minutes, respectively (Manwaring 1973). Ignition occurs upon reactions with many common solvents of the type ketone, lower alcohols, esters, and halogenated hydrocarbons. Such solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, methanol, ethanol, n-propanol, isopropanol, ethyl acetate, n-propyl formate, n-butyl acetate, chloroform, methylene chloride, carbon tetrachloride, epichlorohydrin, dimethyl carbonate, and diethyl sulfate (NFPA 1997).
Flammability and Explosibility Flammable
reaction suitability core: potassium
Purification Methods It sublimes at 220o/1mm. The last traces of tert-BuOH are removed by heating at 150-160o/2mm for 1hour. It is best prepared afresh as likely impurities are tert-BuOH, KOH and K2CO3 depending on its exposure to air. Its solubility at 25-26o in hexane, toluene, Et2O, and THF is 0.27%, 2.27%, 4.34% and 25.0%, respectively. [Feuer et.al. J Am Chem Soc 78 4364, Doering & Urban J Am Chem Soc 78 5938 1956, Beilstein 1 IV 1612.]