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Triethyl phosphite is used as a ligand in organometallic chemistry and as a reagent in organic synthesis. It is used as reference to phosphoric acid standard in 31P NMR spectroscopy. It acts as a reducing agent to prepare 2-phenylindazole from o-nitrobenzylidineaniline as well as reacts with electrophiles to get phosphonates. It forms a stable complex with copper(I) iodide. It finds application in a modified Staudinger reaction for the alkyl bromide to an amine through the azide. Further, it is also used in the preparation of 3-phenyl-2-substituted indoles by reacting with beta-nitro styrenes.
Precursor of phosphonate esters by the Arbuzov reaction. See also Triisopropyl phosphite, A15247. The Arbuzov isomerization to diethyl ethanephosphonate can be induced by a trace of iodine: Synth. Commun., 20, 239 (1990). For reviews of the Arbuzov reaction, see: Org. React., 6, 273 (1951); Chem. Rev., 71, 317 (1971); 81, 415 (1981).
Reaction with acyl halides yields acylphosphonate esters, borohydride reduction of which gives aldehydes: Chem. Ber., 103, 2984 (1970).
Reducing agent: o-nitrobenzylidineaniline gives 2-phenylindazole: Org. Synth. Coll., 5, 941 (1973). For a review of the phosphite reduction of aromatic nitro compounds to heterocycles, see: Synthesis, 11 (1969). Reaction with ß-nitro styrenes forms 3-phenyl-2-substituted indoles in good yields: J. Org. Chem., 57, 6508 (1992).
Use in a modified Staudinger reaction provides a useful one-pot conversion of an alkyl bromide to an amine via the azide: Synthesis, 202 (1985):
For reviews of the Staudinger reaction, see: Tetrahedron, 37, 437 (1981); 48, 353 (1992).
Chmielewska, E.; Miszczyk, P.; Kozłowska, J.; Prokopowicz, M.; Młynarz, P.; Kafarski, P. Reaction of benzolactams with triethyl phosphite prompted by phosphoryl chloride affords benzoannulated monophosphonates instead of expected bisphoshonates. Int. J. Organomet. Chem. 2015, 785, 84-91.
Satheeshkumar, C.; Ravivarma, M.; Rajakumar, P.; Ashokkumar, R.; Jeong, D. C.; Song, C. Synthesis, photophysical and electrochemical properties of stilbenoid dendrimers with phenothiazine surface group. Tetrahedron Lett. 2015, 56 (2), 321-326.
Hazard Statements: H226-H302-H332-H319-H317
Flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes serious eye irritation. May cause an allergic skin reaction.
Precautionary Statements: P262-P273-P280h-P305+P351+P338
Do not get in eyes, on skin, or on clothing. Avoid release to the environment. Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.