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328650 Aldrich

Potassium tert-butoxide solution

1.0 M in THF

Synonym: Potassium tert-butylate, Potassium-2-methylpropan-2-olate solution

  • CAS Number 865-47-4

  • Linear Formula (CH3)3COK

  • Molecular Weight 112.21

  •  Beilstein Registry Number 3556712

  •  MDL number MFCD00012162

  •  PubChem Substance ID 24859391

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Properties

Related Categories Materials Science, Micro/NanoElectronics, Potassium, Solution Deposition Precursors
concentration   1.0 M in THF
density   0.902 g/mL at 25 °C

Description

Frequently Asked Questions

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Packaging

2 L in Sure/Seal™

20 L in steel drum

50, 500 mL in Sure/Seal™

Application

Potassium tert-butoxide is used to prepare 3-potassiooxamethylpyridine catalyst.1 It is also used as a strong alkoxide base reagent.

General description

Potassium tert-butoxide solution is a strong non nucleophilic base. It is capable of deprotonating carbon and other Bronsted acids. Reagent solutions in tert-BuOh may be prepared by reacting anhydrous alcohol with potassium in nitrogen atmosphere.

Price and Availability

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Potassium <I>tert</I>-butoxide solution

1.0 M in tert-butanol

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
May form explosive peroxides.
Hazard Codes (Europe) 
F,C
Risk Statements (Europe) 
Safety Statements (Europe) 
16-26-36/37/39-45
RIDADR 
UN 2924 8(3) / PGII
WGK Germany 
1
Flash Point(F) 
-2.2 °F
Flash Point(C) 
-19 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Acids and Bases

Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This Aldrich product line ranges from Brønsted and Lewis...
Chemfiles Volume 1 Article 3

Peer-Reviewed Papers

References

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1. One-step methodology for the synthesis of FA picolinyl esters from intact lipids. Destaillats F and Angers P J. Am. Oil Chem. Soc. 79(3), 253-256, (2002)

An efficient organocatalytic method for constructing biaryls through aromatic C-H activation. Sun CL, Li H, Yu DG, et al. Nature Chemistry 2(12), 1044-9, (2010)

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A macrocyclic aromatic pyridone pentamer as a highly efficient organocatalyst for the direct arylations of unactivated arenes. Zhao H, Shen J, Guo J, et al. Chem. Commun. (Camb.) 49(23), 2323-5, (2013)

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Formation of 4-aminopyrimidines via the trimerization of nitriles using focused microwave heating. Baxendale IR and Ley SV J. Comb. Chem. 7(3), 483-9, (2005)

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Mizoroki-heck-type reaction mediated by potassium tert-butoxide. Shirakawa E, Zhang X, and Hayashi T Angew. Chem. Int. Ed. Engl. 50(20), 4671-4, (2011)

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Neocuproine-KOtBu promoted intramolecular cross coupling to approach fused rings. Sun CL, Gu YF, Huang WP, et al. Chem. Commun. (Camb.) 47(35), 9813-5, (2011)

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Palladium-catalyzed cross-coupling reactions of silanolates: a paradigm shift in silicon-based cross-coupling reactions. Denmark SE and Baird JD Chemistry 12(19), 4954-63, (2006)

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Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst. Toutov AA, Liu WB, Betz KN, et al. Nature 518(7537), 80-4, (2015)

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Cross coupling: When is free really free? Leadbeater NE Nature Chemistry 2(12), 1007-9, (2010)

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Intramolecular direct dehydrohalide coupling promoted by KO(t)Bu: total synthesis of Amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine. De S, Ghosh S, Bhunia S, et al. Org. Lett. 14(17), 4466-9, (2012)

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Transition-metal-free synthesis of oxindoles by potassium tert-butoxide-promoted intramolecular α-arylation. Beyer A, Buendia J, and Bolm C Org. Lett. 14(15), 3948-51, (2012)

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Lipase-mediated synthesis of water-soluble plant stanol derivatives in tert-butanol. He WS, Li JJ, Pan XX, et al. Bioresour. Technol. 114, 1-5, (2012)

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Simple alcohols promoted direct C-H arylation of unactivated arenes with aryl halides. Liu W, Tian F, Wang X, et al. Chem. Commun. (Camb.) 49(29), 2983-5, (2013)

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3-Aryltetronic acids: efficient preparation and use as precursors for vulpinic acids. Mallinger A, Le Gall T, and Mioskowski C J. Org. Chem. 74(3), 1124-9, (2009)

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Synthesis and characterization of injectable, water-soluble copolymers of tertiary amine methacrylates and poly(ethylene glycol) containing methacrylates. Anderson BC and Mallapragada SK Biomaterials 23(22), 4345-52, (2002)

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Potassium tert-butoxide-mediated regioselective silaboration of aromatic alkenes. Ito H, Horita Y, and Yamamoto E Chem. Commun. (Camb.) 48(64), 8006-8, (2012)

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Pd-catalyzed arylation of silyl enol ethers of substituted alpha-fluoroketones. Guo Y, Twamley B, and Shreeve JM Org. Biomol. Chem. 7(8), 1716-22, (2009)

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New synthetic routes to optically active alpha-quaternary alpha-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet-Hauser rearrangements. Tayama E, Orihara K, and Kimura H Org. Biomol. Chem. 6(20), 3673-80, (2008)

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Synthesis of carbazoles via an intramolecular cyclization of 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines and their related molecules. Lee CY, Lin CF, Lee JL, et al. J. Org. Chem. 69(6), 2106-10, (2004)

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Determination of carbamate, phenylurea and phenoxy acid herbicide residues by gas chromatography after potassium tert-butoxide/dimethyl sulphoxide/ethyl iodide derivatization reaction. Crespo-Corral E, Santos-Delgado MJ, Polo-Díez LM, et al. J. Chromatogr. A 1209(1-2), 22-8, (2008)

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Chemiluminescence in molecular recognition: base-induced decomposition of optically active dioxetanes bearing a bisnaphthol moiety with a complex of optically active crown ether-potassium tert-butoxide. Matsumoto M, Hamaoka K, Takashima Y, et al. Chem. Commun. (Camb.) (6), 808-10, (2005)

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Inhibitors of sterol synthesis. Chemical synthesis of 7 alpha-ethyl and 16 alpha-ethyl derivatives of delta 8(14)-15-oxygenated sterols and their effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase in CHO-K1 cells. Kim HS, Wilson WK, Kirkpatrick ND, et al. Chem. Phys. Lipids 62(1), 55-67, (1992)

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High yielding synthesis of N-ethyl dehydroamino acids. Monteiro LS and Suárez AS Amino Acids 43(4), 1643-52, (2012)

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Transition metal-free addition of ketones or nitriles to 1,3-dienes. Gaudin JM and Millet P Chem. Commun. (Camb.) (5), 588-90, (2008)

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Bioassay monitoring of waste PCB samples during chemical destruction treatments. Takigami H, Behnisch PA, Shiozaki K, et al. Water Sci. Technol. 53(11), 43-50, (2006)

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Utilizing capillary gas chromatography mass spectrometry to determine 4-benzotrifluoride t-butyl ether as a reaction by-product in fluoxetine synthesized using potassium t-butoxide as base. Robbins DK, Dodson PN, Buccilli LA, et al. J. Pharm. Biomed. Anal. 31(1), 63-74, (2003)

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Beil. 1,IV,1612

Fieser 1,911 / Fieser 2,336 / Fieser 3,233 / Fieser 4,399 / Fieser 5,544 / Fieser 6,477 / Fieser 8,407 / Fieser 9,380 / Fieser 10,323 / Fieser 11,432 / Fieser 12,401 / Fieser 13,252 / Fieser 15,271 / Fieser 17,289

Corp MSDS 1 (2), 2896:C / FT-IR 1 (2), 1139:D / RegBook 1 (2), 3059:D / Sax 6, 2270 / Structure Index 1, 484:C:9

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