Trimethyl phosphate

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Trimethyl phosphate
Names
IUPAC name
Trimethyl phosphate
Other names
Methyl phosphate
Phosphoric acid trimethyl ester
TMP
Trimethoxyphosphine oxide
Trimethyl orthophosphate
Properties
C3H9PO4
(CH3O)3PO
Molar mass 140.07 g/mol
Appearance Colorless liquid
Odor Mild, pleasant
Density 1.2144 g/cm3 (20 °C)
1.197 g/cm3 (25 °C)
Melting point −46 °C (−51 °F; 227 K)
Boiling point 197 °C (387 °F; 470 K)
Miscible
Solubility Soluble in alcohols, diethyl ether, gasoline, toluene
Vapor pressure 0.85 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 150 °C (302 °F; 323 K)
Lethal dose or concentration (LD, LC):
840 mg/kg (rat, oral)
Related compounds
Related compounds
Phosphoric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethyl phosphate ((CH3O)3PO) is the trimethyl ester of phosphoric acid.

Properties

Chemical

Trimethyl phosphate is a mild methylating agent, useful for dimethylation of anilines and related heterocyclic compounds.

Physical

Trimethyl phosphate is a viscous colorless or slightly yellow liquid. It is soluble in water and many organic solvents.

Availability

Trimethyl phosphate is sold by chemical suppliers.

Preparation

Trimethyl phosphate is prepared by treating phosphoryl chloride with methanol in the presence of an amine base

POCl3 + 3 CH3OH + 3 R3N → (OCH3)3PO + 3 R3NH+Cl

Projects

  • Solvent for aromatic halogenations and nitrations
  • Color inhibitor for fibers

Handling

Safety

Trimethyl phosphate is irritant, though it does not show high toxicity. Hydrolysis will generate methanol which is toxic. Being non-volatile

Storage

In closed plastic bottles.

Disposal

Adding sodium hydroxide to the compound will hydrolyze it to sodium phosphate and methanol, which can be diluted and flushed down the toilet.

References

Relevant Sciencemadness threads