T84409

Sigma-Aldrich

Triphenylphosphine

ReagentPlus®, 99%

Synonym(s):
Phosphorustriphenyl
Linear Formula:
(C6H5)3P
CAS Number:
Molecular Weight:
262.29
Beilstein/REAXYS Number:
610776
EC Number:
MDL number:
PubChem Substance ID:

vapor density

9 (vs air)

Quality Level

vapor pressure

5 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

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

bp

377 °C (lit.)

mp

79-81 °C (lit.)

functional group

phosphine

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

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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, 25, 100, 500 g in poly bottle
1 kg in poly bottle
10 kg in poly drum

Legal Information

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

signalword

Danger

hazcat

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1B - STOT RE 1 Inhalation

storage_class_code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK Germany

WGK 2

Flash Point F

356.0 °F - closed cup

Flash Point C

180 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Selective hydroformylation of polyunsaturated fats with a rhodium-triphenylphosphine catalyst.
Frankel EN and Thomas FL.
Journal of the American Oil Chemists' Society, 49(1), 10-14 (1972)
New complexes of ruthenium (II) and (III) with triphenylphosphine, triphenylarsine, trichlorostannate, pyridine and other ligands.
Stephenson TA and Wilkinson G.
J. Inorg. Nucl. Chem., 28(4), 945-956 (1966)
Shuxin Wang et al.
Nature communications, 8(1), 848-848 (2017-10-12)
It has long been a challenge to dope metal nanoparticles with a specific number of heterometal atoms at specific positions. This becomes even more challenging if the heterometal belongs to the same group as the host metal because of the...
The Heck reaction in ionic liquids: A multiphasic catalyst system.
Carmichael AJ, et al.
Organic Letters, 1(7), 997-1000 (1999)
Xi Kang et al.
Chemical science, 10(37), 8685-8693 (2019-12-06)
Structural transformations between isomers of nanoclusters provide a platform to tune their properties and understand the fundamental science due to their intimate structure-property correlation. Herein, we demonstrate a reversible transformation between the face-centered cubic (FCC) and icosahedral isomers of Pt1Ag28...
Articles
The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.
Read More

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