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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:
18027-10-6
Molecular Weight:
112.18
Beilstein:
3912148
EC Number:
241-939-8
MDL number:
MFCD00013926
UNSPSC Code:
12352000
PubChem Substance ID:
24859800
NACRES:
NA.22

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
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)

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)
Scope and limitations of sodium and potassium trimethylsilanolate as reagents for conversion of esters to carboxylic acids
Marija L, et al.
Croatica Chemica Acta. Arhiv Za Kemiju, 80, 109-115 (2007)
Synthesis, characterization and some reactions of [(diene) Rh ($\mu$-OSiMe3)] 2
Bogdan M,et al.
Journal of Organometallic Chemistry, 493, 261-266 (1995)
Potassium trimethylsilanolate mediated hydrolysis of nitriles to primary amides
Merchant K
Tetrahedron Letters, 41, 3747-3749 (2000)
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)
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