potassium 2-methylpropan-2-olate

• ChemBase ID: 75187
• Molecular Formular: C4H9KO
• Molecular Mass: 112.21196
• Monoisotopic Mass: 112.02904659
• SMILES: [O-]C(C)(C)C.[K+]
• Canonical SMILES: [O-]C(C)(C)C.[K+]
• InChI: InChI=1S/C4H9O.K/c1-4(2,3)5;/h1-3H3;/q-1;+1
• InChIKey: LPNYRYFBWFDTMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 2-methylpropan-2-olate
• IUPAC Traditional name: potassium ion t-butyl hydroxide; potassium t-butyl hydroxide; potassium 2-methylpropan-2-olate
• Synonyms: Potassium 2-methylpropan-2-olate; Potassium tert-butoxide; potassium 2-methylpropan-2-olate; Potassium tert-butylate; Potassium t-butoxide; Potassium tert-butoxide; Potassium tert-butoxide solution; 次丁氧基钾; 第三丁氧基钾; 叔丁醇钾; 叔丁醇钾 溶液

Database IDs

• CAS Number: 865-47-4
• EC Number: 212-740-3
• MDL Number: MFCD00012162
• Beilstein Number: 3556712
• PubChem SID: 24859954; 24881790; 162040105; 24849626; 24884165; 24859391
• PubChem CID: 23665647; 70077
• Chemspider ID: 63266
• Wikipedia Title: Potassium_tert-butoxide

CALCULATED PROPERTIES

• Acid pKa: 18.086988
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.53538257
• LogD (pH = 7.4): 0.53538257
• Log P: 0.53538257
• Molar Refractivity: 32.6172 cm^3
• Polarizability: 8.423538 Å^3
• Polar Surface Area: 23.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: hydrolysis in water
• Apperance: solid
• Melting Point: 255(dec.)°C; 256°C; 256-258 °C (dec.)(lit.); ca 255°C dec.
• Flash Point: 12 °C; -19 °C; -2.2 °F; 53.6 °F
• Density: 0.82 g/mL at 20 °C; 0.82 g/mL at 25 °C; 0.902 g/mL at 25 °C
• Vapor Pressure: 1 mmHg ( 220 °C)

Safety Information

• Storage Warning: Air & Moisture Sensitive; Highly Flammable/Corrosive/Moisture Sensitive/Air Sensitive/Store under Argon
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924; 3206; 3274; UN3206
• German water hazard class: 1
• Hazard Class: 3; 4.2
• Packing Group: 2; II
• Risk Statements: 11-14-20-35-37; 11-14-34; 11-14-35; 11-19-35-37; R:34
• Safety Statements: 16-26-36/37/39-45; 7/9-16-26-36/37/39-43-45; 7/9-16-26-36/37/39-45-MissingPhraseText-N15.00511280; 8-26-30-36/37/39-45-60; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H252-H314-H332-H335; H225-H314-H335; H228-H251-H314-H318; H228-H252-H314
• GHS Precautionary statements: P210-P235 + P410-P261-P280-P305 + P351 + P338-P310; P210-P235 + P410-P280-P305 + P351 + P338-P310; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2; UN 3206 4.2/PG 2; UN 3274 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.; Reacts violently with water.

Product Information

• Purity: ≥94% (T); ≥97.0% (T); ≥98%; 97%; 98%; 99%; 99.99% trace metals basis
• Concentration: ~1 M in tert-butanol; 1.0 M in tert-butanol; 1.0 M in THF
• Grade: reagent grade; sublimed grade; technical
• Salt Data: K+
• Impurities: ≤2% K2(CO)3 and KOH; ≤3.5% K2CO3 and KOH
• Linear Formula: (CH3)3COK

DETAILS

Sigma Aldrich - 156671

Packaging
100, 500 g in steel can
25 kg in steel drum
2.5 kg in steel can
5, 25 g in glass bottle

Sigma Aldrich - 659878

General description
Total impurities: may contain up to 5,000 ppm Sodium
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 328650

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
2 L in Sure/Seal™
20 L in steel drum
50, 500 mL in Sure/Seal™

Sigma Aldrich - 331341

Packaging
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 60098

Packaging
100, 500 g in glass bottle

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).