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329576

Sigma-Aldrich

Sodium trimethylsilanolate

95%

Synonym(s):

Trimethylsilanol sodium salt

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About This Item

Linear Formula:
(CH3)3SiONa
CAS Number:
Molecular Weight:
112.18
Beilstein:
3912148
EC Number:
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

mp

230 °C (dec.) (lit.)

SMILES string

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

InChI

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

InChI key

HSNUIYJWTSJUMS-UHFFFAOYSA-N

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General description

Sodium trimethylsilanolate is a versatile and very powerful reagent for the conversion of esters to carboxylic acids and the hydrolysis of nitriles to primary amides. It can be used as a starting material for the synthesis of metal silanolates via the salt metathesis and as a catalyst for the silylation of silanols with hydrosilanes.

Application

Sodium trimethylsilanolate is used as a catalyst in the:
  • Synthesis of the rhodium silonate complex.
  • Silylation of methylphenylsilane with tert-butyldimethylsilanol to synthesize trisiloxanes.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

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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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, 109-115 (2007)
Potassium trimethylsilanolate mediated hydrolysis of nitriles to primary amides
Merchant K
Tetrahedron Letters, 41, 3747-3749 (2000)
Synthesis, characterization and some reactions of [(diene) Rh ($\mu$-OSiMe3)] 2
Bogdan M,et al.
Journal of Organometallic Chemistry, 493, 261-266 (1995)
Silylation of silanols with hydrosilanes via main-group catalysis: the synthesis of unsymmetrical siloxanes and hydrosiloxanes
Krzysztof K, et al.
Inorganic chemistry frontiers, 7, 4190-4196 (2020)
Silylation of silanols with hydrosilanes via main-group catalysis: the synthesis of unsymmetrical siloxanes and hydrosiloxanes
Kucinski K, et al.
Inorganic chemistry frontiers, 7, 4190-4196 (2020)

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