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T84409 Sigma-Aldrich

Triphenylphosphine

ReagentPlus®, 99%

Synonym: Phosphorustriphenyl

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Properties

Related Categories Basic Phosphine Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling, Phosphine Compounds,
Quality Level   200
grade   ReagentPlus®
vapor density   9 (vs air)
vapor pressure   5 mmHg ( 20 °C)
assay   99%
bp   377 °C (lit.)
mp   79-81 °C (lit.)
functional group   phosphine
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: ligand
reaction type: Cross Couplings
SMILES string   c1ccc(cc1)P(c2ccccc2)c3ccccc3
InChI   1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChI key   RIOQSEWOXXDEQQ-UHFFFAOYSA-N

Description

General description

Rhodium and triphenylphosphine catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters. Polymer supported triphenylphosphine has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate. Triphenylphosphine reacts with hydrated ruthenium trichloride in methanol to afford [RuCl2(PPh3)4], [RuCl2(PPh3)3] and [RuCl3(PPh3)2CH3OH]. It participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.

Application

Triphenylphosphine was used in the synthesis of mono-6-amino-deoxy-6-cyclodextrin. It was also employed as catalyst during the synthesis of C-aryl furanosides.

Packaging

1 kg in poly bottle

1, 25, 100, 500 g in poly bottle

10 kg in poly drum

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Nervous system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
SZ3500000
Flash Point(F) 
356 °F
Flash Point(C) 
180 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

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Chemical Synthesis

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Keywords: Medicinal chemistry

Peer-Reviewed Papers
15

References

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