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

L00339 Triethyl phosphite, 98%

CAS-Nummer
122-52-1
Synonyme
Phosphorous acid triethyl ester

Größe Preis ($) Menge Verfügbarkeit
100ml 16,56
500ml 34,30
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Triethyl phosphite, 98%

MDL
MFCD00009084
EINECS
204-552-5

Chemische Eigenschaften

Formel
C6H15O3P
Molmasse
166.16
Schmelzpunkt
-112°
Siedepunkt
155-157°
Flammpunkt
43°(109°F)
Dichte
0.958
Brechungsindex
1.4130
Sensitivität
Air & Moisture Sensitive
Löslichkeit
Miscible with alcohol and ether. Immiscible with water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): 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.

Sicherheitshinweise: 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.

Weitere Referenzen

Beilstein
956578
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2920.90
TSCA
Yes
RTECS
TH1130000

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