Trimethyl phosphite

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Trimethyl phosphite
Trimethyl phosphite structure.svg
Trimethyl phosphite Ball and Stick.png
Trimethyl phosphite Space Fill.png
IUPAC name
Trimethyl phosphite
Other names
3D model (JSmol)
ECHA InfoCard 100.004.065
Molar mass 124.08
Appearance colorless liquid
Odor distinctive, pungent[1]
Density 1.052
Melting point −78 °C (−108 °F; 195 K)
Boiling point 111 °C (232 °F; 384 K)
Vapor pressure 24 mmHg (25°C)[1]
Flash point 28 °C; 82 °F; 301 K [1]
US health exposure limits (NIOSH):
PEL (Permissible)
REL (Recommended)
TWA 2 ppm (10 mg/m3)[1]
IDLH (Immediate danger)
Related compounds
Related compounds
Dimethyl methylphosphonate
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

Trimethylphosphite is [2] an organophosphorus compound with the formula P(OCH3)3, often abbreviated P(OMe)3. This colorless liquid is used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The molecule features a pyramidal phosphorus(III) center bound to three methoxide groups.

Synthesis and reactions[edit]

Although commercially available, trimethylphosphite is prepared from phosphorus trichloride:

Synthesis of Trimethyl phosphite

It is susceptible to oxidation to trimethyl phosphate.

As a ligand, trimethylphosphite has a smaller cone angle and better acceptor properties relative to trimethylphosphine. A representative derivative is the colorless, tetrahedral complex Ni(P(OMe)3)4 (m.p. 108 °C).[3] The tridentate ligand called the Klaui ligand is derived from trimethylphosphite. The formation of this ligand illustrates the susceptibility of trimethylphosphite (and metal complexes thereof) to the Arbuzov reaction.

Trimethylphosphite is also used as a mild desulfurization reagent in organic synthesis, for example in the preparation of derivatives of tetrathiafulvalene.[4]


  1. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0640". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ A comprehensive guide to the hazardous properties of chemical substances - Pradyot Patnaik - Google Kitaplar
  3. ^ Ittel, Steven D.; Ittel, S. D.; Cushing, M. A.; Baker, R.; Gilbert, R. J.; Madden, D. P. (1990). "Complexes of Nickel(0)". Inorganic Syntheses. Inorganic Syntheses. 28: 98–104. ISBN 978-0-471-52619-3. doi:10.1002/9780470132593.ch25. 
  4. ^ Jan Larsen and Christine Lenoir (1998). "2,2'-Bi-5,6-Dihydro-1,3-Dithiolo[4,5-b][1,4]dithiinylidene (BEDT-TTF)". Org. Synth. ; Coll. Vol., 9, p. 72 .

External links[edit]