Trimethyl phosphate

Trimethyl phosphate

Names
Preferred IUPAC name Trimethyl phosphate
Other names Phosphoric acid trimethyl ester Methyl phosphate, Trimethoxyphosphine oxide Trimethyl orthophosphate
Identifiers
CAS Number	512-56-1 Y
3D model (Jmol)	Interactive image
Abbreviations	TMP
ChEBI	CHEBI:46324 Y
ChemSpider	10101 Y
ECHA InfoCard	100.007.405
PubChem CID	10541
InChI InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3 Y Key: WVLBCYQITXONBZ-UHFFFAOYSA-N Y InChI=1/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3 Key: WVLBCYQITXONBZ-UHFFFAOYAV
SMILES O=P(OC)(OC)OC
Properties
Chemical formula	(CH3O)3PO
Molar mass	140.08
Appearance	Colorless liquid
Melting point	−46 °C (−51 °F; 227 K)
Boiling point	197 °C (387 °F; 470 K)
Solubility in water	good
Hazards
EU classification (DSD)	Harmful substances or preparations (Xn)
R-phrases	R22,R36/37/38
S-phrases	S36/37,S45
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Trimethyl phosphate is the trimethyl ester of phosphoric acid. It is a colourless, nonvolatile liquid. It has some specialized uses in the production of other compounds.

Trimethyl phosphate is prepared by treating phosphorus oxychloride with methanol in the presence of an amine base:

It is a tetrahedral molecule that is a weakly polar solvent.

Trimethyl phosphate is a mild methylating agent, useful for dimethylation of anilines and related heterocyclic compounds. The method is complementary to the traditional Eschweiler-Clarke reaction in cases where formaldehyde engages in side reactions.

Trimethyl phosphate is used as a solvent for aromatic halogenations and nitrations as required for the preparation of pesticides and pharmaceuticals.

It is used as a color inhibitor for fibers (e.g. polyester) and other polymers.

With an LD50 of 2g/kg for rats, trimethylphosphate is expected to have low acute toxicity.