Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

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

L02502 Triphenylphosphine, powder, 99%

CAS Number
603-35-0
Synonyms
TPP

Size Price ($) Quantity Availability
50g 25.83
250g 58.87
1000g 166.40
Add to Cart Add to Quote Request View Item

Triphenylphosphine, powder, 99%

MDL
MFCD00003043
EINECS
210-036-0

Chemical Properties

Formula
(C6H5)3P
Formula Weight
262.29
Melting point
79-81°
Boiling Point
360°
Flash Point
181°(358°F)
Density
1.200
Solubility
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.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H373-H302-H317

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

Precautionary Statements: 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.

Other References

Merck
14,9743
Beilstein
610776
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
SZ3500000

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware