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14221-01-3 molecular structure
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tetrakis(triphenylphosphane) palladium

ChemBase ID: 9830
Molecular Formular: C72H60P4Pd
Molecular Mass: 1155.561844
Monoisotopic Mass: 1154.26803444
SMILES and InChIs

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

Cite this record

CBID:9830 http://www.chembase.cn/molecule-9830.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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)
CAS Number
14221-01-3
EC Number
238-086-9
MDL Number
MFCD00010012
Beilstein Number
6704828
PubChem SID
24873549
160973137
24852971
24846942
24888926
PubChem CID
11979704

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 5.1066  LogD (pH = 7.4) 5.1066 
Log P 5.1066  Molar Refractivity 81.6229 cm3
Polarizability 32.34495 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds 12  Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Soluble in benzene, ethanol and chloroform expand Show data source
Apperance
Crystalline expand Show data source
Melting Point
100-105°C expand Show data source
100-105°C expand Show data source
103-107°C expand Show data source
Storage Warning
Air Sensitive expand Show data source
Harmful/Irritant/Air Sensitive/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold expand Show data source
MOISTURE SENSITIVE, STORED UNDER ARGON expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
53 expand Show data source
Safety Statements
36/37 expand Show data source
60-61 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351 expand Show data source
H413 expand Show data source
GHS Precautionary statements
P273-P501A expand Show data source
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97.0% (Pd) expand Show data source
≥99.99% trace metals basis expand Show data source
98% expand Show data source
99% expand Show data source
99.8% (metals basis), Pd 9% min expand Show data source
Grade
purum expand Show data source
Particle Size
200-400 mesh expand Show data source
Certificate of Analysis
Download expand Show data source
Extent of Labeling
~0.06 mmol/g loading expand Show data source
0.5-0.9 mmol/g loading expand Show data source
Matrix
crosslinked with 1% DVB expand Show data source
Magnesium aluminometasilicate base material expand Show data source
Crosslinking
2 % cross-linked with divinylbenzene expand Show data source
Linear Formula
Pd[(C6H5)3P]4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05219414 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - 685364 external link
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 external link
Application
Polymer-bound catalyst for Suzuki Coupling reactions.1,,,2
Packaging
1, 5 g in glass bottle
Sigma Aldrich - 10987 external link
Other Notes
Polymer bound palladium catalyst1
Packaging
1, 5 g in glass bottle
Sigma Aldrich - 216666 external link
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 external link
Packaging
2 g in glass bottle
500 mg in glass bottle
Application
Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Sigma Aldrich - 87645 external link
Other Notes
Review1,2
Application
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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