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 ;
3D model (JSmol)	Interactive image;
Abbreviations	TMP
ChEBI	CHEBI:46324 ;
ChemSpider	10101 ;
ECHA InfoCard	100.007.405
PubChem CID	10541;
UNII	Z1E45TMW1Z ;
CompTox Dashboard (EPA)	DTXSID1021403 ;
	InChI InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3 Key: WVLBCYQITXONBZ-UHFFFAOYSA-N ; 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EU classification (DSD) (outdated)	Harmful substances or preparations (Xn)
R-phrases (outdated)	R22,R36/37/38
S-phrases (outdated)	S36/37,S45
NFPA 704 (fire diamond)	1 2 0
	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]

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.
William A. Sheppard (1973). "m-Trifluoromethyl-N,N-dimethylaniline". Organic Syntheses.; Collective Volume, 5, p. 1085
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

External links

WebBook page for C3H9PO4

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[1] D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.

[2] William A. Sheppard (1973). "m-Trifluoromethyl-N,N-dimethylaniline". Organic Syntheses.; Collective Volume, 5, p. 1085

[3] 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