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Sodium trimethylsilanolate

Name: Sodium trimethylsilanolate
Brand: ALDRICH

95%

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Synonym(s):

Trimethylsilanol sodium salt

Linear Formula:

(CH₃)₃SiONa

CAS Number:

18027-10-6

Molecular Weight:

112.18

Beilstein:

3912148

EC Number:

241-939-8

MDL number:

MFCD00013926

PubChem Substance ID:

24859800

NACRES:

NA.22

Quality Level

100

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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Related Categories

Caustic Alkalis & Bases

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

GHS05

Signal Word

Danger

Hazard Statements

H314

Precautionary Statements

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

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

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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)

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)

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)