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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/REAXYS Number:
3912148
EC Number:
241-939-8
MDL number:
MFCD00013926
UNSPSC Code:
12352000
PubChem Substance ID:
24859800
NACRES:
NA.22

Quality Level

100

assay

95%

form

powder

mp

230 °C ((lit.))
230 °C (dec.) (lit.)

SMILES string

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

InChI

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

InChI key

[HSNUIYJWTSJUMS-UHFFFAOYSA-N]
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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4486
MKCN9500
MKCN9499
MKCN9715
MKCN3069

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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)
D M Hui et al.
Clinica chimica acta; international journal of clinical chemistry, 302(1-2), 171-188 (2000-11-14)
We developed a new assay method for fluoride anion (F(-)) a specific metabolite of sarin. Trimethyifluorosilane (TMFS) was derivatized from F(-) with trimethylsilanol, and TMFS was detected with a GC-flame ionization detector (FID) and capillary column system. The linear range
A Isquith et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 26(3), 263-266 (1988-03-01)
Six organosilicon compounds which had been found to have clastogenic activity in an in vitro battery of genotoxicity assays were evaluated in rat bone marrow cytogenetic assays for assessing clastogenicity in an in vivo system. None of the six compounds
Igor S Ignatyev et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 60(5), 1169-1178 (2004-04-16)
The assignment of the SiOH group vibrations of trimethylsilanol, which is still controversial, is proposed. This assignment is based on theoretical B3LYP force field scaled using the constants of the (CH3)3Si group optimized to fit experimental vibrational frequencies of (CH3)3SiF
Fabricio A Hansel et al.
Rapid communications in mass spectrometry : RCM, 25(13), 1893-1898 (2011-06-04)
A methodology is presented for the determination of dihydroxy fatty acids preserved in the 'bound' phase of organic residues preserved in archaeological potsherds. The method comprises saponification, esterification, silica gel column chromatographic fractionation, and analysis by gas chromatography/mass spectrometry. The
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