tetrakis(triphenylphosphane) palladium

• ChemBase ID: 9830
• Molecular Formular: C72H60P4Pd
• Molecular Mass: 1155.561844
• Monoisotopic Mass: 1154.26803444
• SMILES: c1(P(c2ccccc2)c2ccccc2)ccccc1.c1(P(c2ccccc2)c2ccccc2)ccccc1.c1(P(c2ccccc2)c2ccccc2)ccccc1.c1(P(c2ccccc2)c2ccccc2)ccccc1.[Pd]
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Pd]
• InChI: InChI=1S/4C18H15P.Pd/c4*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h4*1-15H
• InChIKey: NFHFRUOZVGFOOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrakis(triphenylphosphane) palladium
• IUPAC Traditional name: tetrakis(triphenylphosphine) palladium
• Synonyms: Tetrakis(triphenylphosphine)palladium (0); Palladium(0) tetrakis(triphenylphosphine); Tetrakis(triphenylphosphine)palladium; Tetrakis(triphenylphosphine)palladium(0); PALLADIUM TETRAKIS-(TRIPHENYLPHOSPHINE); Palladium-tetrakis(triphenylphosphine), polymer-bound; Tetrakis(triphenylphosphine)palladium, polymer-bound; ChemDose™, Tetrakis(triphenylphosphine)palladium(0) impregnated tablets; Palladium-tetrakis(triphenylphosphine) impregnated tablets; Tetrakis[triphenylphosphine]palladium(0), ChemDose™ tablets; Pd(PPh3)4; Palladium-tetrakis(triphenylphosphine); Tetrakis(triphenylphosphine)palladium(0); 四(三苯基膦)钯; 聚合物键合型四(三苯基膦)钯; 四(三苯基膦)钯，聚合物键合型; ChemDose™，四(三苯基膦)钯(0) 浸渍片; 四(三苯基膦)钯浸渍片; 四(三苯基膦)钯(0)，ChemDose™ 片; 四(三苯基膦)钯; 四(三苯基膦)钯(0)

Database IDs

• CAS Number: 14221-01-3
• EC Number: 238-086-9
• MDL Number: MFCD00010012
• Beilstein Number: 6704828
• PubChem SID: 24852971; 24846942; 24873549; 24888926; 160973137
• PubChem CID: 11979704

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3
• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in benzene, ethanol and chloroform
• Apperance: Crystalline
• Melting Point: 100-105°C; 100-105°C; 103-107°C

Safety Information

• Storage Warning: Air Sensitive; Harmful/Irritant/Air Sensitive/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; MOISTURE SENSITIVE, STORED UNDER ARGON
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40; 53
• Safety Statements: 36/37; 60-61
• TSCA Listed: false; 是
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351; H413
• GHS Precautionary statements: P273-P501A; P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (Pd); ≥99.99% trace metals basis; 98%; 99%; 99.8% (metals basis), Pd 9% min
• Grade: purum
• Particle Size: 200-400 mesh
• Extent of Labeling: ~0.06 mmol/g loading; 0.5-0.9 mmol/g loading
• Matrix: crosslinked with 1% DVB; Magnesium aluminometasilicate base material
• Crosslinking: 2 % cross-linked with divinylbenzene
• Linear Formula: Pd[(C6H5)3P]4

DETAILS

MP Biomedicals - 05219414

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 685364

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Legal Information
ChemDose is a trademark of Reaxa Ltd.

Sigma Aldrich - 511579

Application
Polymer-bound catalyst for Suzuki Coupling reactions.1,,,2
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 10987

Other Notes
Polymer bound palladium catalyst1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 216666

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
1, 5, 25, 100 g in glass bottle
Application

• Catalyst for Negishi coupling (eq. 1), Suzuki coupling (eq. 2), Stille coupling (eq. 3), and Sonogashira coupling reaction (eq. 4)
• Catalyst for Buchwald-Hartwig amination reaction (eq. 5)
• Catalyst for the carbonylation of vinyl iodides (eq. 6)
• Catalyst for reduction reaction of aryl bromides (eq. 7)
• Catalyst for carbon-tin bond formation (eq. 8)
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Sigma Aldrich - 697265

Packaging
2 g in glass bottle
500 mg in glass bottle
Application
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Sigma Aldrich - 87645

Other Notes
Review1,2
Application
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

REFERENCES

• The conversion of aryl halides or triflates to benzonitriles can be much improved by the use of the catalyst in combination with Zn(CN)₂ in DMF or NaCN/CuI (cat) in acetonitrile, giving good yields at lower temperatures than the classical Rosenmund-von Braun method (see Copper(I) cyanide, 12135): Tetrahedron Lett., 39, 2907 (1998); J. Org. Chem., 63, 8224 (1998). Vinyl bromides or iodides with KCN/18-crown-6 give acrylonitriles in high yield with retention of configuration: Tetrahedron Lett., 4429 (1977). Vinyl triflates with LiCN can also be used: J. Chem. Soc., Chem. Commun., 756 (1989). For a review of palladium- and copper-catalyzed cyanation reactions, see: Eur. J. Inorg. Chem., 3513 (2004).
• Allylic esters, halides, etc. form organopalladium intermediates equivalent to allyl cations and react with various nucleophiles, e.g. amines: J. Am. Chem. Soc., 98, 8516 (1976); J. Org. Chem., 44, 3451 (1979); Tetrahedron Lett., 24, 2745 (1983); Org. Synth. Coll., 8, 13 (1993). For stereoselective introduction of an amino group using sodium azide, see: J. Org. Chem., 54, 3292 (1989).
• Catalyst for a variety of carbonylation reactions. Aryl, vinyl, benzylic and allylic halides with CO (1-3 atm) in the presence of Bu₃SnH give aldehydes: J. Am. Chem. Soc., 105, 7175 (1983); 108, 452 (1986). For carbonylative intramolecular cyclization of aminomethyl vinyl triflates to ɑ?-unsaturated lactams, see: Tetrahedron, 51, 5585 (1995):
  
• Acyl halides can be coupled with organometallic reagents to give ketones, e.g. organozinc halides: Tetrahedron Lett., 24, 5181 (1983); Org. Synth. Coll., 8, 274 (1993), organotin reagents: Org. Synth. Coll., 8, 268 (1993), or arylboronic acids: Tetrahedron Lett., 40, 3109 (1999).
• Homogeneous catalyst for a wide variety of organometallic coupling reactions.
• Numerous methods have been developed for the synthesis of unsymmetrical biaryls, many of which are catalyzed by this Pd(0) complex. Aryl halides or triflates can be coupled with, e.g. Grignard reagents: Tetrahedron, 42, 2111 (1986), arylzinc halides: Org. Synth. Coll., 8, 430 (1993), organotin reagents (Stille): Angew. Chem. Int. Ed., 25, 508 (1986); J. Am. Chem. Soc., 109, 5478 (1987), or boronic acids (Suzuki-Miyaura): Synth. Commun., 11, 513 (1981); Chem. Rev., 95, 257 (1995); see Benzeneboronic acid, A14257, and Appendix 5.
• Vinyl iodides couple stereoselectively with alkyl, aryl or vinyl Grignards: Tetrahedron Lett., 191 (1978). For stereoselective arylation of a vinylic bromide with an arylzinc chloride in a synthesis of the anti-estrogen agent (Z)-tamoxifen and derivatives, see: J. Org. Chem., 55, 6184 (1990):
  
• For an example of the coupling of a terminal acetylene with a vinyl bromide by the Sonogashira method using Copper(I) iodide, 11606, see: Org. Synth. Coll., 9, 117 (1998).