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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
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grade

technical grade

Quality Level

200

Assay

90%

form

powder

concentration

≤100%

mp

135-138 °C (lit.)
135-138 °C

SMILES string

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

InChI

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

InChI key

LBKJNHPKYFYCLL-UHFFFAOYSA-N
LBKJNHPKYFYCLL-UHFFFAOYSA-N

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Application

Potassium trimethylsilanolate can be used as a reagent in the:
  • Hydrolysis of nitriles to primary amides.[1]
  • Conversion of esters to carboxylic acids,[2] and dialkyl phosphonates to their monoalkyl phosphonates.[3]
  • Synthesis of E-alkenes,[4] and nitrocefin.[5]


It can also be used as a coupling promoter in cross-coupling reaction of aliphatic alkynylsilanols with aryl iodides.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000396917
0000396943
0000388795
0000368540
0000357726

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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)
A practical synthesis of nitrocefin
Lee M, et al.
The Journal of Organic Chemistry, 70(1), 367-369 (2005)
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)
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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