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603-35-0 - Triphenylphosphine, powder, 99% - TPP - L02502 - Alfa Aesar

L02502 Triphenylphosphine, powder, 99%

CAS-Nummer
603-35-0
Synonyme
TPP

Größe Preis ($) Menge Verfügbarkeit
50g 29,00
250g 64,10
1000g 210,00
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Triphenylphosphine, powder, 99%

MDL
MFCD00003043
EINECS
210-036-0

Chemische Eigenschaften

Formel
(C6H5)3P
Molmasse
262.29
Schmelzpunkt
79-81°
Siedepunkt
360°
Flammpunkt
181°(358°F)
Dichte
1.200
Löslichkeit
Soluble in ether, benzene, carbon tetrachloride, glacial acetic acid, acetone, chloroform and alcohol. Insoluble in water.

Anwendungen

Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. The anionic phosphine is usually isolated as the trisodium salt, which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions. It is also used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyse C-C coupling reactions in organic synthesis.

Bemerkungen

Incompatible with oxidizing agents and acids.

Literaturverweise

Finds widespread use as a complexing agent with transition metals, either in the preparation of stable complexes, or as an additive in metal-promoted reactions. See also Tri(o-tolyl)­phosphine, A12093 and Tri(2-furyl)­phosphine, L13329.

Azides can be converted selectively to amines, in the presence of ester, epoxide or nitro groups, by reduction to iminophosphoranes (Staudinger reaction), followed by hydrolysis. For reviews, see: Tetrahedron, 37, 437 (1981); 48, 1353 (1992):

In suitable circumstances, the iminophosphorane may undergo intramolecular aza-Wittig reaction: Tetrahedron, 45, 6375 (1989):

Reviews: Aza-Wittig reaction in heterocyclic synthesis: Org. Prep. Proced. Int., 24, 209 (1992); Iminophosphoranes as building blocks for the preparation of N-containing heterocycles: Synthesis, 1197 (1994).

For use in peptide and other coupling reactions, see 2,2'-Dipyridyl­ disulfide, A11118.

For use in the Mitsunobu reaction for conversion of alcohols to alkylating agents, see N-Guanyl­urea sulfate, A19106, and Diisopropyl­ azodicarboxyl­ate, L10386. See also 1,2-Bis(diphenyl­phosphino)­ethane, A11419.

Loghmani, M. H.; Shojaei, A. F. Reduction of cobalt ion improved by lanthanum and zirconium as a triphenylphosphine stabilized nano catalyst for hydrolysis of sodium borohydride. Int. J. Hydrogen Energy 2015, 40 (20), 6573-6581.

Nirmala, M.; Prakash, G.; Viswanathamurthi, P.; Malecki, J. G. An attractive route to transamidation catalysis: Facile synthesis of new o-aryloxide-N-heterocyclic carbene ruthenium (II) complexes containing trans triphenylphosphine donors. J. Mol. Catal. A: Chem. 2015, 403, 15-26.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302-H317-H373

Harmful if swallowed. May cause an allergic skin reaction. May cause damage to organs through prolonged or repeated exposure.

Sicherheitshinweise: P260-P280g-P301+P312a-P363-P321-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves. IF SWALLOWED: Wash contaminated clothing before reuse. Specific treatment (see label). Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,9743
Beilstein
610776
Harmonized Tariff Code
2931.39
TSCA
Yes
RTECS
SZ3500000

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