Potassium tert-butoxide

• Catalog No.: A13947
• CAS Number: 865-47-4
• M. F.: C4H9KO
• M. W.: 112.21196
• Purity: 97%

SYNONYMS

• Title: 叔丁醇钾
• IUPAC name: potassium 2-methylpropan-2-olate
• IUPAC Traditional name: potassium 2-methylpropan-2-olate
• Synonyms: Potassium tert-butylate

DATABASE IDS

• Beilstein Number: 3556712
• EC Number: 212-740-3
• MDL Number: MFCD00012162
• CAS Number: 865-47-4

PROPERTIES

• Purity: 97%
• Melting Point: ca 255°C dec.
• GHS Hazard statements: H228-H251-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-14-34
• Safety Statements: 8-26-30-36/37/39-45-60
• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 4.2
• UN Number: UN3206
• Packing Group: II

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.
• 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.
• 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).