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865-47-4 Usage

Chemical Description

Potassium tert-butoxide is a strong base used in organic chemistry.

Strong organic alkaline

Potassium tert-butoxide is an important kind of organic base with its alkalinity being stronger than potassium hydroxide. Because of the induction effect of three methyl groups in the (CH3) 3CO-, it 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. Therefore, potassium tert-butoxide has attracted more and more attention from chemical, pharmaceutical, pesticide and other industries. As potassium tert-butoxide has such a wide application, the domestic and international demand for high purity potassium tert-butoxide is very large. However, due to its production cost is higher than other alkali metal alkoxides, the production technology needs to be improved, so in-depth study of potassium tert-butoxide is particularly important.

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. It can be manufactured through the reaction between butanol and potassium, followed by the vacuum distillation of tert-butanol in the system. Potassium tert-butoxide is used as a strong non-nucleophilic base in organic chemistry. It is widely used the condensation reaction, rearrangement and ring-opening reaction in organic synthesis. People generally apply tert-butanol solution. Potassium tert-butoxide is a kind of organic alkaline corrosion products with strong moisture absorption property and should be sealed for storage. We need to pay attention to prevention of fire and sunshine during the storage and transportation. It should be stored in a cool, ventilated and dry place.

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 ReactionsPotassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions

Uses

Different sources of media describe the Uses of 865-47-4 differently. You can refer to the following data:
1. 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.
2. Usually used for greener amidation of esters.
3. Potassium tert-Butoxide is used in the synthesis of many organic compounds primarily as a strong base. In particular, it is used as a reagent in the base- catalyzed carbonylation of amines for the synthesis of N-Formamides.

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 lookchem.

Chemical Properties

white crystalline powder

General Description

This product has been enhanced for catalytic efficiency.

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). Such ignition may arise from accidental contact of the alkoxide with these solvents and may be attributed to sudden release of energy from exothermic reactions. However, slow mixing of the powder with excess solvent will dissipate the heat. It reacts violently with water, producing tert-butanol and potassium hydroxide, as follows:K―OC―(C4H9)3+H2O → tert-C4H9OH +KOH The addition of potassium tert-butoxide to the solvent dimethyl sulfoxide can cause ignition of the latter (Bretherick 1995).

Flammability and Explosibility

Flammable

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 865-47-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,6 and 5 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 865-47:
(5*8)+(4*6)+(3*5)+(2*4)+(1*7)=94
94 % 10 = 4
So 865-47-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O.K/c1-4(2,3)5;/h5H,1-3H3;/q;+1

865-47-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A13947)  Potassium tert-butoxide, 97%   

  • 865-47-4

  • 25g

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A13947)  Potassium tert-butoxide, 97%   

  • 865-47-4

  • 100g

  • 356.0CNY

  • Detail
  • Alfa Aesar

  • (A13947)  Potassium tert-butoxide, 97%   

  • 865-47-4

  • 250g

  • 492.0CNY

  • Detail
  • Alfa Aesar

  • (A13947)  Potassium tert-butoxide, 97%   

  • 865-47-4

  • 500g

  • 883.0CNY

  • Detail
  • Alfa Aesar

  • (A13947)  Potassium tert-butoxide, 97%   

  • 865-47-4

  • 1000g

  • 1590.0CNY

  • Detail
  • Aldrich

  • (156671)  Potassiumtert-butoxide  reagent grade, ≥98%

  • 865-47-4

  • 156671-5G

  • 503.10CNY

  • Detail
  • Aldrich

  • (156671)  Potassiumtert-butoxide  reagent grade, ≥98%

  • 865-47-4

  • 156671-25G

  • 510.12CNY

  • Detail
  • Aldrich

  • (156671)  Potassiumtert-butoxide  reagent grade, ≥98%

  • 865-47-4

  • 156671-100G

  • 696.15CNY

  • Detail
  • Aldrich

  • (156671)  Potassiumtert-butoxide  reagent grade, ≥98%

  • 865-47-4

  • 156671-500G

  • 1,647.36CNY

  • Detail
  • Aldrich

  • (156671)  Potassiumtert-butoxide  reagent grade, ≥98%

  • 865-47-4

  • 156671-2.5KG

  • 5,692.05CNY

  • Detail
  • Aldrich

  • (659878)  Potassiumtert-butoxide  sublimed grade, 99.99% trace metals basis

  • 865-47-4

  • 659878-5G

  • 607.23CNY

  • Detail
  • Aldrich

  • (659878)  Potassiumtert-butoxide  sublimed grade, 99.99% trace metals basis

  • 865-47-4

  • 659878-25G

  • 1,993.68CNY

  • Detail

865-47-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Potassium tert-butanolate

1.2 Other means of identification

Product number -
Other names potassium,2-methylpropan-2-olate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Laboratory chemicals
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:865-47-4 SDS

865-47-4Synthetic route

tert-butyl alcohol
75-65-0

tert-butyl alcohol

potassium tert-butylate
865-47-4

potassium tert-butylate

Conditions
ConditionsYield
With potassium amalgam; catalyst comprising porous iron for 2.2h; Conversion of starting material;
With potassium amalgam; catalyst comprising porous iron for 1.7h; Conversion of starting material;
With potassium amalgam; nonporous iron for 15h; Conversion of starting material;
2-phenethyl iodide
17376-04-4

2-phenethyl iodide

potassium tert-butylate
865-47-4

potassium tert-butylate

styrene
292638-84-7

styrene

Conditions
ConditionsYield
In tert-butyl alcohol at 40℃; Rate constant; Mechanism; secondary α-deuterium isotope effects investigated;100%
1-fluoro-2-phenylethane
458-87-7

1-fluoro-2-phenylethane

potassium tert-butylate
865-47-4

potassium tert-butylate

styrene
292638-84-7

styrene

Conditions
ConditionsYield
18-crown-6 ether In tert-butyl alcohol at 40℃; Rate constant; Mechanism; secondary α-deuterium isotope effects investigated; also in absence of catalyst;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

2-phenylethyl chloride
622-24-2

2-phenylethyl chloride

styrene
292638-84-7

styrene

Conditions
ConditionsYield
18-crown-6 ether In tert-butyl alcohol at 40℃; Rate constant; Mechanism; secondary α-deuterium isotope effects investigated; also in absence of catalyst;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

styrene
292638-84-7

styrene

Conditions
ConditionsYield
In tert-butyl alcohol at 40℃; Rate constant; Mechanism; secondary α-deuterium isotope effects investigated;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

tert-butyl-4-bromobenzoate
59247-47-1

tert-butyl-4-bromobenzoate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;100%
In diethyl ether for 1h; Substitution;95%
In tetrahydrofuran at -78 - 20℃; for 2h;95%
potassium tert-butylate
865-47-4

potassium tert-butylate

benzylmercury(II) chloride
2117-39-7

benzylmercury(II) chloride

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

dibenzylmercury(II)
780-24-5

dibenzylmercury(II)

Conditions
ConditionsYield
In dimethyl sulfoxide Hg deriv. adding to a stirred soln. of potassium tert-butoxide and diethyl phosphite in N2-purged DMSO, stirring for 5 min;100%
In dimethyl sulfoxide Hg deriv. adding to a stirred soln. of potassium tert-butoxide and diethyl phosphite in N2-purged DMSO, stirring for 39.5 h;51%
C14H25B9N2

C14H25B9N2

potassium tert-butylate
865-47-4

potassium tert-butylate

C14H24B9N2(1-)*K(1+)

C14H24B9N2(1-)*K(1+)

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
tert-butyl 4-(2,6-dichloro-4-pyridyl)pyrrolo[2,3-b]pyridine-1-carboxylate

tert-butyl 4-(2,6-dichloro-4-pyridyl)pyrrolo[2,3-b]pyridine-1-carboxylate

potassium tert-butylate
865-47-4

potassium tert-butylate

4-(2-tert-butoxy-6-chloro-4-pyridyl)-1H-pyrrolo[2,3-b]pyridine

4-(2-tert-butoxy-6-chloro-4-pyridyl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: tert-butyl 4-(2,6-dichloro-4-pyridyl)pyrrolo[2,3-b]pyridine-1-carboxylate; potassium tert-butylate In toluene at 100℃; for 5h;
Stage #2: With hydrogenchloride In water; toluene for 0.166667h;
100%
2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

potassium tert-butylate
865-47-4

potassium tert-butylate

2-(tert-butoxy)-3-chloropyrazine

2-(tert-butoxy)-3-chloropyrazine

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Inert atmosphere; Cooling with ice;100%
C12H7ClINO

C12H7ClINO

potassium tert-butylate
865-47-4

potassium tert-butylate

tert-butyl (4-chloro-2-iodophenyl)(propa-1,2-dien-1-yl)carbamate

tert-butyl (4-chloro-2-iodophenyl)(propa-1,2-dien-1-yl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

1,1,4,4-tertakis(trimethylsilyl)octamethylcyclohexasilane
99548-02-4

1,1,4,4-tertakis(trimethylsilyl)octamethylcyclohexasilane

C17H51Si9(1-)*K(1+)

C17H51Si9(1-)*K(1+)

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

C35H45FeN4O2(1+)*I(1-)

C35H45FeN4O2(1+)*I(1-)

C39H54FeN4O3

C39H54FeN4O3

Conditions
ConditionsYield
In benzene-d6 for 0.333333h; Inert atmosphere;100%

865-47-4Upstream product

865-47-4Relevant articles and documents

Unusual Reactivity of Silicon Grease Towards Metal Alkoxides: Serendipity for Structural Chemistry

Nahrstedt, Vanessa,Raauf, Aida,Hegemann, Corinna,Brune, Veronika,Schl?fer, Johannes,Mathur, Sanjay

, p. 1102 - 1109 (2021)

Controlled synthesis of moisture sensitive metal alkoxides demands the use of silicon grease for the inert synthetic manipulation of starting materials using glass apparatus to avoid adventitious hydrolysis. Spontaneous reaction of the siloxane units (?OSi(Me3)2)n) with the synthesized alkoxides often leads to molecular metal alkoxides based siloxane frameworks. These spontaneous incorporation of siloxane units into homo- and heterometallic alkoxide building blocks lead to the new multinuclear homo- and heterometallic alkoxide-siloxide compounds [Ce2(OtBu)4{Me2Si(OtBu)O}2(NO3)2] (1), [Zr{(OiPr)2{Me2SiO2}Sr{Zr2(OiPr)8}}2] (2) and [Sn2In2O2{Me2Si(OiPr)O}(OiPr)5]2 (3). Multifunctional coordination properties of these siloxane units enable the molecular approach to synthetically demanding polymetallic complexes for potential MOx-SiOx nanocomposites fabrication.

Efficient Synthesis of N-Substituted 2,4-Azepandione Ring System as an Active Intermediate for Heterocyclic Syntheses

Waly, Mohamed A.,Yossif, Shiam A.,Ibrahim, Ismail T.,Sofan, Mamdouh A.

, p. 1318 - 1326 (2017/03/27)

An improved efficient synthesis for 2,4-azepandiones (3, 8, and 14) could be achieved by a careful control of the reaction conditions to cyclize ethyl 4-(N-acetylarylamino) butanoate (1, 7, and 13), respectively. The ethyl 4-arylamino butanoate (9 or 12) was prepared by stirring the ethyl 4-bromobutanoate and substituted anilines at room temperature. Then, they were acetylated with acetyl chloride and triethylamine under the conditions that avoid the formation of 2-pyrrolidinone derivatives 10. Due to the rapid decomposition of the acetylated product (7 or 13) to its starting material (9 or 12), the reaction mixture is directly transferred without workup to the next cyclization step. The azepandione synthesis is favored by using a weak base at low temperature, where it is in a competition with the other modes of ring closure. The structures of the new compounds were supported by correct analytical and spectral data.

Preparation method for low residual granular sodium alkoxide or potassium alcoholate

-

Paragraph 0039-0040, (2017/01/17)

The invention provides a preparation method for low residual granular sodium alkoxide or potassium alcoholate. The method includes using sodium or potassium and alcohol as raw materials, mixing the mixture with a solvent, reacting in inert gas atmosphere by using a microwave heating method, and removing the residual alcohol and solvent in the presence of microwave after the reaction to get the granular sodium alkoxide or potassium alcoholate. The microwave frequency is 2450 +/- 50 MHz. The method can prepare sodium alkoxide or potassium alcoholate with low residual solvent, and the prepared sodium alkoxide or potassium alcoholate is large granular solid, so that the development from powdered product to granular product can be realized, and the problems of residual solvent and potential risk troubled human for a long time can be overcome.

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