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

L00339 Triethyl phosphite, 98%

Codice CAS
122-52-1
Sinonimi
Phosphorous acid triethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 16,56
500ml 34,30
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Triethyl phosphite, 98%

MDL
MFCD00009084
EINECS
204-552-5

Proprietà chimiche

Formula
C6H15O3P
Peso formula
166.16
Punto di fusione
-112°
Punto di ebollizione
155-157°
Punto di infiammabilità
43°(109°F)
Densità
0.958
Indice di rifrazione
1.4130
Sensibilità
Air & Moisture Sensitive
Solubilità
Miscible with alcohol and ether. Immiscible with water.

Applicazioni

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 <sup>31</sup>P 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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
956578
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2920.90
TSCA
Yes
RTECS
TH1130000

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