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

L02502 Triphenylphosphine, powder, 99%

Numéro CAS
603-35-0
Synonymes
TPP

Dimensions Prix ($) Quantité Disponibilité
50g 25,83
250g 58,87
1000g 166,40
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Triphenylphosphine, powder, 99%

MDL
MFCD00003043
EINECS
210-036-0

Propriétés chimiques

Formule
(C6H5)3P
Poids formulaire
262.29
Point de fusion
79-81°
Point d'ébullition
360°
Point d'éclair
181°(358°F)
Densité
1.200
Solubilité
Soluble in ether, benzene, carbon tetrachloride, glacial acetic acid, acetone, chloroform and alcohol. Insoluble in water.

Applications

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(PPh<sub>3</sub>)<sub>3</sub> 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.

Notes

Incompatible with oxidizing agents and acids.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H373-H302-H317

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

Mentions de prudence: P260-P261-P280-P264-P270-P301+P312-P363-P321-P333+P313-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. Do not eat, drink or smoke when using this product. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Specific treatment (see label). If skin irritation or rash occurs: Get medical advice/attention. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,9743
Beilstein
610776
Code tarifaire harmonisé
2931.90
TSCA
Yes
RTECS
SZ3500000

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