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865-47-4 - Potassium tert-butoxide, 97% - Potassium tert-butylate - A13947 - Alfa Aesar

A13947 Potassium tert-butoxide, 97%

CAS Number
865-47-4
Synonyms
Potassium tert-butylate

Size Price ($) Quantity Availability
25g 23.76
100g 36.18
250g 51.91
500g 94.55
1000g 167.89
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Potassium tert-butoxide, 97%

MDL
MFCD00012162
EINECS
212-740-3

Chemical Properties

Formula
C4H9KO
Formula Weight
112.22
Melting point
ca 255° dec.
Sensitivity
Air & Moisture Sensitive
Solubility
Soluble in hexane, toluene, diethyl ether and terahydrofuran.

Applications

Potassium tert-butoxide is used as a strong non-nucleophilic base in organic chemistry. It plays an active role in dehydrohalogenation reactions. It is also useful for greener amidation of esters. It serves as an intermediate in Mizoroki-Heck-type reactions. Furthermore, it is used as an initiator in anionic polymerization of carbazolyl-substituted oxiranes. It catalyzes the reaction of hydrosilanes and heterocyclic compounds to give the silyl derivatives with evolution of hydrogen.

Notes

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with water, acids, reducing agents, oxygen, alcohols, chlorinated solvents, halogens and ketones.

Literature References

Strong base of relatively low nucleophilicity. Review: Chem. Rev., 74, 45 (1974). The nucleophilicity is increased in the presence of 18-crown-6; the basic strength less so: J. Org. Chem., 43, 447 (1978).

For generation of dibromocarbene, see Bromoform, A11904. In combination with a solid-liquid phase-transfer catalyst in the absence of solvent, has been recommended for the dehydrobromination of alkyl bromides to alkenes: J. Org. Chem., 49, 1138 (1984): with 18-crown-6, is effective for the dehydrobromination of vic-dibromides: Liebigs Ann. Chem., 1 (1980), and in the dehydrochlorination of gem-dichloroalkanes to give alkynes: J. Org. Chem., 39, 3285 (1974).

Deprotonation of an ɑ-halo sulfone, followed by Ramberg-Backlund reaction with extrusion of SO2, gives an alkene: J. Am. Chem. Soc., 110, 4866 (1988); Org. React., 25, 1 (1977); Org. Synth. Coll., 8, 212 (1993):

For cyclization-elimination of ɑɑ-dibromoneopentyl ketone to di-tert-butylcyclopropenone, a precursor of tri-tert-butylcyclopropenium tetrafluoroborate, see: Org. Synth. Coll., 6, 991 (1988); for reaction scheme, see Neopentyl­ chloride, L02365.

For intramolecular cyclization of a dinitrile to an unsaturated vic-amino nitrile (Thorpe-Ziegler reaction), see: Org. Synth. Coll., 6, 932 (1988).

Treatment of a methyl ester in ether with the reagent provides a simple method for preparation of tert-butyl esters: Synlett, 658 (2001).

Combinations of KO-t-Bu with other strong bases are used to generate "superbasic" media, e.g. with n-BuLi: J. Organomet. Chem., 8, 9 (1967); Pure Appl. Chem., 60, 1627 (1988); Tetrahedron Lett., 29, 4991 (1988); see also Phenyl­acetyl­ene, A12139, 2-Methyl­indole, A10764, etc. In combination with Li 3-aminopropanamide, promotes the "zip" reaction for isomerizing alkynes to the terminal position; see 1,3-Diaminopropane, A11932, and Org. Synth. Coll., 8, 146 (1993). For use in combination with LDA for isomerization of epoxides to allylic alcohols, see Cyclohexene oxide, A13185.

Suzuki, C.; Kato, K.; Tsuji, A. B.; Zhang, M. R.; Arano, Y.; Saga, T. Inhibition of radical reactions for an improved potassium tert-butoxide-promoted 11C-methylation strategy for the synthesis of alfa-11C-methyl amino acids. J. Labelled Compd. Radiopharm. 2015, 58 (3), 127-132.

Midya, G. C.; Kapat, A.; Maiti, S.; Dash, J. Transition-Metal-Free Hydration of Nitriles Using Potassium tert-Butoxide under Anhydrous Conditions. J. Org. Chem. 2015, 80 (8), 4148-4151.

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H251-H314-H318

Flammable solid. Self-heating: may catch fire. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3556712
Hazard Class
4.2
Packing Group
II
Harmonized Tariff Code
2905.19
TSCA
Yes

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