Trimethyl phosphite

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Trimethyl phosphite
Trimethyl phosphite structure.svg
Names
IUPAC name
Trimethyl phosphite
Other names
Trimethoxyphosphine
Identifiers
121-45-9 YesY
ChemSpider 8159 YesY
Jmol-3D images Image
PubChem 8472
Properties
C3H9O3P
Molar mass 124.08
Appearance colorless liquid
Density 1.052
Melting point −78 °C (−108 °F; 195 K)
Boiling point 111 °C (232 °F; 384 K)
organic solvents
Related compounds
Related compounds
Dimethyl methylphosphonate
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Trimethylphosphite is [1] 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).[2] 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.[3]

References[edit]

  1. ^ A comprehensive guide to the hazardous properties of chemical substances - Pradyot Patnaik - Google Kitaplar
  2. ^ 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. doi:10.1002/9780470132593.ch25. ISBN 978-0-471-52619-3. 
  3. ^ 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]