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205885 Aldrich

Palladium(II) chloride

ReagentPlus®, 99%

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Essential Chemicals, Homogeneous Pd Catalysts, Materials Science,
grade   ReagentPlus®
assay   99%
form   powder
mp   678-680 °C(lit.)
density   4 g/mL at 25 °C(lit.)

Description

Analysis Note

Used as a catalyst together with Cu(II) for deamination of phenethylamine to phenyl substituted pyrroles.2 Efficient Suzuki coupling of aryl chlorides with aryl boronic acids using catalytic PEG (300)-PdCl2.3

Packaging

1, 5, 25, 100 g in glass bottle

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Used in the synthesis of semiconducting metal-containing polymers in which the polypyrrole backbone has a conformational energy minimum and is nearly planar.1

Legal Information

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

Price and Availability


Ultra-high Purity Salts

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Safety & Documentation

Safety Information

RIDADR 
UN 3288 6.1 / PGIII
WGK Germany 
3
RTECS 
RT3500000

Protocols & Articles

Articles

Changing the Landscape of Environmental and Energy Research Through Novel Nanoscale Materials

Energy and environmental catalysts (EECs) form a major group of materials that will continue to drive the growth of industry and research investments. The EEC market is estimated to be between $10−16...
Santanu Chaudhuri
Material Matters, 2012 v7, n4
Keywords: Adsorption, Alternative energy, Applications, Automotive, Catalysis, Diffusion, Environmental, Gene expression, Immobilization, Infrared spectroscopy, Metal organic frameworks, Methods, Molecular probes, Oxidations, Protocols, Reductions, Search, Spectroscopy, Substitutions, Support, Surface Science, Type

Supported/Encapsulated Palladium Catalysts

Palladium has become one of the most commonly used metal for cross-coupling transformations. However, the use of homogeneous palladium presents several drawbacks that can be overcome by attaching the...
William Sommer
Aldrich ChemFiles 2007, 7.10, 23.
Keywords: Carbonylations, Catalysis, Chemfiles, Coupling reactions, Cross couplings, Immobilization, Ligands

Peer-Reviewed Papers

References

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1. Mathis, M. et al. Chem. Mater. 10, 3568, (1998)

2. Multiple deprotonations and deaminations of phenethylamines to synthesize pyrroles. J. Am. Chem. Soc. 128, 12046, (2006)

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3. Tetrahedron 62, 9339, (2006)

Synthesis of Enantiopure Indolizidine Alkaloids from alpha-Amino Acids: Total Synthesis of (-)-Indolizidine 167B. Angle, S. R.; Henry, R. M. J. Org. Chem. 62, 8549, (1997)

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Triethanolamine-mediated palladium-catalyzed regioselective C-2 direct arylation of free NH-pyrroles. Jafarpour, F.; Rahiminejadan, S.; Hazrati, H. J. Org. Chem. 75, 3109, (2010)

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Pd(OH)2/C (Pearlman's catalyst): a highly active catalyst for Fukuyama, Sonogashira, and Suzuki coupling reactions. Mori Y, Seki M. J. Org. Chem. 68, 1571, (2003)

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Metal allergen of the 21st century--a review on exposure, epidemiology and clinical manifestations of palladium allergy. Faurschou A, Menné T, Johansen JD, et al. Contact Dermatitis 64(4), 185-95, (2011)

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[Comparative studies on the genotoxic activity of a new palladium (II) acidocomplex vs cisplatin in human blood lymphocytes in vitro]. Grekhova AK, Gorbacheva LB, Ivanova NA, et al. Biomed. Khim. 59(1), 107-14, (2013)

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Highly dispersed pd catalyst locked in knitting aryl network polymers for Suzuki-Miyaura coupling reactions of aryl chlorides in aqueous media. Li B, Guan Z, Wang W, et al. Adv. Mater. 24(25), 3390-5, (2012)

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PdCl2-catalyzed oxidative cycloisomerization of 3-cyclopropylideneprop-2-en-1-ones. Miao M, Cao J, Zhang J, et al. Org. Lett. 14(11), 2718-21, (2012)

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Flexible diphosphine ligands with overall charges of 0, +1, and +2: critical role of the electrostatics in favoring trans over cis coordination. Canac Y, Debono N, Lepetit C, et al. Inorg. Chem. 50(21), 10810-9, (2011)

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Comparison between pre-fractionation and fractionation process of heavy gas oil for determination of sulfur compounds using comprehensive two-dimensional gas chromatography. Machado ME, Bregles LP, de Menezes EW, et al. J. Chromatogr. A 1274, 165-72, (2013)

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Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media. Liu C, Ni Q, Hu P, et al. Org. Biomol. Chem. 9(4), 1054-60, (2011)

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Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides. Hu Z, Liang D, Zhao J, et al. Chem. Commun. (Camb.) 48(59), 7371-3, (2012)

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Pd(II)-mediated cyclization of o-allylbenzaldehydes in water: a novel synthesis of isocoumarins. Chen PY, Huang KS, Tsai CC, et al. Org. Lett. 14(18), 4930-3, (2012)

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The nature of [PdCl(2)(C(2)H(4))(H(2)O)] as an active species in the Wacker process: new insights from ab initio molecular dynamics simulations. Kovács G, Stirling A, Lledós A, et al. Chemistry 18(18), 5612-9, (2012)

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Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation. Velcicky J, Soicke A, Steiner R, et al. J. Am. Chem. Soc. 133(18), 6948-51, (2011)

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Metal patch test results from 1990-2009. Nonaka H, Nakada T, Iijima M, et al. J. Dermatol. 38(3), 267-71, (2011)

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[(RCN)2PdCl2]-catalyzed E/Z isomerization of alkenes: a non-hydride binuclear addition-elimination pathway. Tan EH, Lloyd-Jones GC, Harvey JN, et al. Angew. Chem. Int. Ed. Engl. 50(41), 9602-6, (2011)

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PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions. Yuan FQ, Gao LX, and Han FS Chem. Commun. (Camb.) 47(18), 5289-91, (2011)

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Interaction of adenine with palladium chloride, determination of adenine via resonance Rayleigh scattering method. Xu Q, Liu Z, Hu X, et al. Anal. Chim. Acta 707(1-2), 114-20, (2011)

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Crystal structure, electronic properties and cytotoxic activity of palladium chloride complexes with monosubstituted pyridines. Krogul A, Cedrowski J, Wiktorska K, et al. Dalton Trans. 41(2), 658-66, (2012)

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Probing the origin of the metabolic precursor of the CO ligand in the catalytic center of [NiFe] hydrogenase. Bürstel I, Hummel P, Siebert E, et al. J. Biol. Chem. 286(52), 44937-44, (2011)

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An efficient palladium catalyst system for the oxidative carbonylation of glycerol to glycerol carbonate. Hu J, Gu Y, Guan Z, et al. ChemSusChem 4(12), 1767-72, (2011)

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Synthesis of 4H-cyclopenta[c]furans via cooperative PdCl2-FeCl2 catalyzed cascade cyclization reaction involving a novel acyl rearrangement process. Jiang H, Pan X, Huang L, et al. Chem. Commun. (Camb.) 48(39), 4698-700, (2012)

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Contact allergy to metals in adolescents: nickel release from metal accessories 7 years after the implementation of the EU Nickel Directive in Poland. Krecisz B, Chomiczewska D, Palczynski C, et al. Contact Dermatitis 67(5), 270-6, (2012)

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The Suzuki reaction in aqueous media promoted by P, N ligands. Weeden JA, Huang R, Galloway KD, et al. Molecules 16(8), 6215-31, (2011)

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Characterization of hydrogen responsive nanoporous palladium films synthesized via a spontaneous galvanic displacement reaction. Patton JF, Lavrik NV, Joy DC, et al. Nanotechnology 23(46), 465403, (2012)

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Evaluation of cytotoxicity of new trans-palladium(II) complex in human cells in vitro. Kontek R, Matławska-Wasowska K, Kalinowska-Lis U, et al. Acta Pol. Pharm. 68(1), 127-36, (2011)

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Spectrophotometric complexation of cephalosporins with palladium (II) chloride in aqueous and non-aqueous solvents. Bagheri Gh A, Yosefi rad A, Rezvani M, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 89, 317-21, (2012)

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Variability in patch test reactivity over time, falsely indicating patch test sensitization, in a patient tested with palladium salts. Engfeldt M, Tillman C, Hindsén M, et al. Contact Dermatitis 67(2), 109-11, (2012)

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Merck 14,6990

Fieser 1,782 / Fieser 2,303 / Fieser 4,369 / Fieser 5,500 / Fieser 6,447 / Fieser 7,277 / Fieser 8,384 / Fieser 9,352 / Fieser 10,300 / Fieser 11,393 / Fieser 12,371 / Fieser 13,234 / Fieser 15,248 / Fieser 16,268

Corp MSDS 1 (2), 2673:D / Corp MSDS 1 (2), 2673:C / RegBook 1 (3), 3339:E / Sax 6, 2113

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