Tetramethyl orthosilicate

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Tetramethyl orthosilicate
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Names
IUPAC name
tetramethoxysilane
Other names
tetramethyl orthosilicate; methyl silicate; silicic acid, tetramethyl ester; silicon methoxide; TMOS
Identifiers
681-84-5 YesY
ChemSpider 12161 YesY
Jmol 3D model Interactive image
PubChem 12682
  • InChI=1S/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3 YesY
    Key: LFQCEHFDDXELDD-UHFFFAOYSA-N YesY
  • InChI=1/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3
    Key: LFQCEHFDDXELDD-UHFFFAOYAT
  • CO[Si](OC)(OC)OC
Properties
SiC4H12O4
Molar mass 152.25
Appearance colourless liquid
Density 1.032
Melting point 4 to 5 °C (39 to 41 °F; 277 to 278 K)
Boiling point 121 to 122 °C (250 to 252 °F; 394 to 395 K)
organic solvents
Vapor pressure 12 mmHg (25°C)[1]
Vapor pressure {{{value}}}
Related compounds
Other cations
 Trimethyl borate
Trimethyl phosphite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Tetramethyl orthosilicate is the chemical compound with the formula Si(OCH3)4. This molecule consists of four methyl groups attached to the hypothetical anion SiO44−. The basic properties are similar to the more popular tetraethyl orthosilicate, which is usually preferred because the product of hydrolysis, ethanol, is less toxic than methanol.

Tetramethyl orthosilicate hydrolyzes to SiO2:

Si(OCH3)4 + 2 H2O → SiO2 + 4 CH3OH

In organic synthesis, Si(OCH3)4 has been used to convert ketones and aldehydes to the corresponding ketals and acetals, respectively.[2]

Safety

The hydrolysis of Si(OCH3)4 produces insoluble SiO2 and CH3OH (methanol). Even at low concentrations inhalation causes lung lesions, and at slightly higher concentrations eye contact with the vapor causes blindness. Worse, at low concentrations (200ppm/15min) the damage is often insidious, with onset of symptoms hours after exposure.[3] The mode of action is the precipitation of silica in the eyes and/or lungs. Contrary to common information, including several erroneous MSDS sheets, the methanol produced is relatively innocuous. The mechanisms of methanol toxicity are well established, methanol causes blindness via conversion to toxic formaldehyde in the liver; methanol splashes to the eye cause only moderate and reversible eye irritation.[4]

Tetraethyl orthosilicate is safer for two reasons. 1) It is considerably less volatile. 2) It is hydrolyzed more slowly by the water in the lungs and on the eyes (due to steric bulk).

References

  1. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. ↑ Sakurai, H. "Silicon(IV) Methoxide" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons. doi:10.1002/047084289X.rs012
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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