Trimethyl phosphate
| Ball-and-stick model of trimethyl phosphate | |
| Names | |
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| Other names
phosphoric acid trimethyl ester
TMP methyl phosphate, trimethoxyphosphine oxide trimethyl orthophosphate |
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| Identifiers | |
512-56-1  |
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| ChEBI | CHEBI:46324 |
| ChemSpider | 10101 |
| Jmol 3D model | Interactive image |
| PubChem | 10541 |
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| Properties | |
| (CH3)3PO4 | |
| Molar mass | 140.08 |
| Appearance | Colorless liquid |
| Melting point | −46 °C (−51 °F; 227 K) |
| Boiling point | 197 °C (387 °F; 470 K) |
| good | |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.[1]
Contents
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.
Safety considerations
With an LD50 of 2g/kg for rats, trimethylphosphate is expected to have low acute toxicity.[3]
References
- ↑ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a19_545.pub2
