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Sigma-Aldrich

Potassium trimethylsilanolate

90%, technical grade

Synonym(s):

Trimethylsilanol potassium salt

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About This Item

Linear Formula:
(CH3)3SiOK
CAS Number:
10519-96-7
Molecular Weight:
128.29
Beilstein:
3560282
EC Number:
234-062-7
MDL number:
MFCD00013421
UNSPSC Code:
12352302
PubChem Substance ID:
24859472
NACRES:
NA.22

grade

technical grade

Quality Level

200

Assay

90%

mp

135-138 °C (lit.)

SMILES string

[K+].C[Si](C)(C)[O-]

InChI

1S/C3H9OSi.K/c1-5(2,3)4;/h1-3H3;/q-1;+1

InChI key

LBKJNHPKYFYCLL-UHFFFAOYSA-N

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Application

Potassium trimethylsilanolate can be used as a reagent in the:
  • Hydrolysis of nitriles to primary amides.
  • Conversion of esters to carboxylic acids, and dialkyl phosphonates to their monoalkyl phosphonates.
  • Synthesis of E-alkenes, and nitrocefin.


It can also be used as a coupling promoter in cross-coupling reaction of aliphatic alkynylsilanols with aryl iodides.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cross-coupling of alkynylsilanols with aryl halides promoted by potassium trimethylsilanolate
Denmark SE and Tymonko SA
The Journal of Organic Chemistry, 68(23), 9151-9154 (2003)
Tetrahedron Letters, 25, 5831-5831 (1984)
Potassium trimethylsilanolate-mediated conversion of dialkyl phosphonates to their anhydrous potassium monoalkyl phosphonates under mild, non-aqueous conditions
Dziemidowicz J, et al.
Synthesis, 2005(04), 569-574 (2005)
Scope and limitations of sodium and potassium trimethylsilanolate as reagents for conversion of esters to carboxylic acids
Lovric M, et al.
Croatica Chemica Acta. Arhiv Za Kemiju, 80(1), 109-115 (2007)
Alkene synthesis: elimination of arenesulfinic acid from alkyl aryl sulfones using potassium trimethylsilanolate as base
Baker-Glenn CAG, et al.
Tetrahedron Letters, 46(43), 7427-7430 (2005)
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