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T84409

Sigma-Aldrich

Triphenylphosphine

ReagentPlus®, 99%

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Synonym(s):
Phosphorustriphenyl
Linear Formula:
(C6H5)3P
CAS Number:
603-35-0
Molecular Weight:
262.29
Beilstein:
610776
EC Number:
210-036-0
MDL number:
MFCD00003043
PubChem Substance ID:
24900530

vapor density

9 (vs air)

Quality Level

200

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

H302 - H317 - H318 - H372

Hazard Classifications

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

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

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

Regulatory Information

危险化学品

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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)
Triphenylphosphine: a catalyst for the synthesis of C-aryl furanosides from furanosyl halides.
Nicolas L, et al.
Tetrahedron Letters, 55(4), 849-852 (2014)
Facile synthesis of mono-6-amino-6-deoxy-a-, ?-, ?-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery.
Tang W and Ng S-C.
Nature Protocols, 3(4), 691-697 (2008)
The Heck reaction in ionic liquids: A multiphasic catalyst system.
Carmichael AJ, et al.
Organic Letters, 1(7), 997-1000 (1999)
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