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122-52-1 - Triethyl phosphite, 98% - Phosphorous acid triethyl ester - L00339 - Alfa Aesar

L00339 Triethyl phosphite, 98%

Numéro CAS
Phosphorous acid triethyl ester

Dimensions Prix ($) Quantité Disponibilité
100ml 18,60
500ml 34,80
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Triethyl phosphite, 98%


Propriétés chimiques

Poids formulaire
Point de fusion
Point d'ébullition
Point d'éclair
Indice de réfraction
Air & Moisture Sensitive
Miscible with alcohol and ether. Immiscible with water.


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.


Air and moisture sensitive. Incompatible with strong oxidizing agents and strong bases.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H302-H332-H319-H317-H402-H412

Flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes serious eye irritation. May cause an allergic skin reaction. Harmful to aquatic life. Harmful to aquatic life with long lasting effects.

Mentions de prudence: 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.

Autres références

Classe de danger
Groupe d'emballage
Code tarifaire harmonisé


Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux


Analytique et matériel de laboratoire