Trimethyl phosphate
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.[1]
Production
Trimethyl phosphate is prepared by treating phosphorus oxychloride with methanol in the presence of an amine base:
- POCl3 + 3 CH3OH + 3 R3N → PO(OCH3)3 + 3 R3NH+Cl−
It is a tetrahedral molecule that is a weakly polar solvent.
Applications
Trimethyl phosphate is a mild methylating agent, useful for dimethylation of anilines and related heterocyclic compounds.[2] 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.
Other applications
It is used as a color inhibitor for fibers (e.g. polyester) and other polymers. Trimethyl phosphate is used as a simulant for chemical weapon nerve agents.Script error: No such module "Unsubst".
Safety considerations
With an LD50 of 2g/kg for rats, trimethylphosphate is expected to have low acute toxicity.[3]
References
External links
- ↑ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. Template:ISBN.
- ↑ Template:OrgSynth
- ↑ J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. Script error: No such module "doi".