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Tetramethyl orthosilicate

Chemical compound From Wikipedia, the free encyclopedia

Tetramethyl orthosilicate (TMOS) is the chemical compound with the formula Si(OCH3)4. This molecule consists of four methoxy groups bonded to a silicon atom. It is the tetramethyl ester of orthosilicic acid. 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.

Quick facts Names, Identifiers ...
Tetramethyl orthosilicate
Names
IUPAC name
Tetramethyl orthosilicate
Other names
  • Tetramethyl orthosilicate
  • Methyl silicate
  • Silicic acid, tetramethyl ester
  • Silicon methoxide
  • TMOS
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.598 Edit this at Wikidata
UNII
  • InChI=1S/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3 checkY
    Key: LFQCEHFDDXELDD-UHFFFAOYSA-N checkY
  • InChI=1/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3
    Key: LFQCEHFDDXELDD-UHFFFAOYAT
  • CO[Si](OC)(OC)OC
Properties
Si(OCH3)4
Molar mass 152.221 g·mol−1
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]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
toxic
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
2
0
Flash point 96 °C; 205 °F; 369 K[1]
NIOSH (US health exposure limits):
PEL (Permissible)
none[1]
REL (Recommended)
TWA 1 ppm (6 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
Related compounds
Other cations
Tetraethyl orthosilicate
Trimethyl borate
Trimethyl phosphite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[citation needed]. At low concentrations (200 ppm per 15 min) 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[citation needed]. Contrary to common information, including several erroneous MSDS sheets, the methanol produced is only a risk through chronic exposure and is a comparatively small concern. The mechanisms of methanol toxicity are well established, methanol causes blindness via conversion to formaldehyde, then to toxic formic acid in the liver; methanol splashes to the eye cause only moderate and reversible eye irritation.[4]

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