Palladium(II) bromide

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Palladium(II) bromide
Unit cell of PdBr2.png
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.033.248 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 236-588-2
PubChem CID
  • InChI=1S/2BrH.Pd/h2*1H;/q;;+2/p-2
    Key: INIOZDBICVTGEO-UHFFFAOYSA-L
  • Br[Pd]Br
Properties
Br2Pd
Molar mass 266.228 g/mol
Related compounds
Other anions
Palladium(II) fluoride
Palladium(II) chloride
Palladium(II) iodide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Palladium(II) bromide is an inorganic compound of palladium and bromine with the chemical formula PdBr2. It is a commercially available, although less common than palladium(II) chloride, the usual entry point to palladium complexes. It is a diamagnetic solid.

Contents

Structure

PdBr2-ribbon-side-tilt-from-xtal-Mercury-3D-balls.png

As confirmed by X-ray crystallography, PdBr2 is a coordination polymer. [1] It crystallises in the P21/c space group and the structure consists of wavy ribbons of edge-sharing PdBr4 coordination squares. [2]

PdBr2-xtal-packing-A-axis-tilt-Mercury-3D-balls.png PdBr2-xtal-packing-B-axis-Mercury-3D-balls.png

Reactions

Palladium(II) bromide is insoluble in water but dissolves when heated in acetonitrile to give monomeric acetonitrile adducts: [3]

PdBr2 + 2 MeCN → PdBr2(MeCN)2

PdBr2 exhibits many of the properties of palladium chloride and palladium acetate, giving catalysts active for carbonylations and cross-coupling reactions. [4]

Related Research Articles

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound. A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions.

The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.

<span class="mw-page-title-main">Palladium(II) chloride</span> Chemical compound

Palladium(II) chloride, also known as palladium dichloride and palladous chloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value in organic synthesis. It is prepared by the reaction of chlorine with palladium metal at high temperatures.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

<span class="mw-page-title-main">Molybdenum(V) chloride</span> Chemical compound

Molybdenum(V) chloride is the inorganic compound with the empirical formula MoCl5. This dark volatile solid is used in research to prepare other molybdenum compounds. It is moisture-sensitive and soluble in chlorinated solvents.

The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.

There are three sets of Indium halides, the trihalides, the monohalides, and several intermediate halides. In the monohalides the oxidation state of indium is +1 and their proper names are indium(I) fluoride, indium(I) chloride, indium(I) bromide and indium(I) iodide.

<span class="mw-page-title-main">Sodium tetraphenylborate</span> Chemical compound

Sodium tetraphenylborate is the organic compound with the formula NaB(C6H5)4. It is a salt, wherein the anion consists of four phenyl rings bonded to boron. This white crystalline solid is used to prepare other tetraphenylborate salts, which are often highly soluble in organic solvents. The compound is used in inorganic and organometallic chemistry as a precipitating agent for potassium, ammonium, rubidium, and cesium ions, and some organic nitrogen compounds.

<span class="mw-page-title-main">Sodium tetrachloropalladate</span> Chemical compound

Sodium tetrachloropalladate is an inorganic compound with the chemical formula Na2PdCl4. This salt, and the analogous alkali metal salts of the form M2PdCl4, may be prepared simply by reacting palladium(II) chloride with the appropriate alkali metal chloride in aqueous solution. Palladium(II) chloride is insoluble in water, whereas the product dissolves:

<span class="mw-page-title-main">Bis(acetonitrile)palladium dichloride</span> Chemical compound

Bis(acetonitrile)palladium dichloride is the coordination complex with the formula PdCl2(NCCH3)2. It is the adduct of two acetonitrile ligands with palladium(II) chloride. It is a yellow-brown solid that is soluble in organic solvents. The compound is a reagent and a catalyst for reactions that require soluble Pd(II). The compound is similar to bis(benzonitrile)palladium dichloride. It reacts with 1,5-cyclooctadiene to give dichloro(1,5‐cyclooctadiene)palladium.

<span class="mw-page-title-main">Metal halides</span>

Metal halides are compounds between metals and halogens. Some, such as sodium chloride are ionic, while others are covalently bonded. A few metal halides are discrete molecules, such as uranium hexafluoride, but most adopt polymeric structures, such as palladium chloride.

<span class="mw-page-title-main">Brookhart's acid</span> Chemical compound

Brookhart's acid is the salt of the diethyl ether oxonium ion and tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BAr′4). It is a colorless solid, used as a strong acid. The compound was first reported by Volpe, Grant, and Brookhart in 1992.

<span class="mw-page-title-main">Bromopentaamminecobalt(III) bromide</span> Chemical compound

Bromopentaamminecobalt(III) bromide is the dibromide salt of the cobalt coordination compound with the formula [Co(NH3)5Br]2+. It is a purple, water-soluble solid. The analogous chloropentaamminecobalt(III) chloride is also well known.

<span class="mw-page-title-main">Transition-metal allyl complex</span>

Transition-metal allyl complexes are coordination complexes with allyl and its derivatives as ligands. Allyl is the radical with the connectivity CH2CHCH2, although as a ligand it is usually viewed as an allyl anion CH2=CH−CH2, which is usually described as two equivalent resonance structures.

In chemistry, compounds of palladium(III) feature the noble metal palladium in the unusual +3 oxidation state (in most of its compounds, palladium has the oxidation state II). Compounds of Pd(III) occur in mononuclear and dinuclear forms. Palladium(III) is most often invoked, not observed in mechanistic organometallic chemistry.

<span class="mw-page-title-main">Dithiobenzoic acid</span> Chemical compound

Dithiobenzoic acid is the organosulfur compound with the formula C6H5CS2H. It is a dithiocarboxylic acid, an analogue of benzoic acid, but more acidic and deeply colored.

<span class="mw-page-title-main">Bis(benzonitrile)palladium dichloride</span> Chemical compound

Bis(benzonitrile)palladium dichloride is the coordination complex with the formula PdCl2(NCC6H5)2. It is the adduct of two benzonitrile (PhCN) ligands with palladium(II) chloride. It is a yellow-brown solid that is soluble in organic solvents. The compound is a reagent and a precatalyst for reactions that require soluble Pd(II). A closely related compound is bis(acetonitrile)palladium dichloride.

<span class="mw-page-title-main">Transition metal nitrile complexes</span> Class of coordination compounds containing nitrile ligands (coordinating via N)

Transition metal nitrile complexes are coordination compounds containing nitrile ligands. Because nitriles are weakly basic, the nitrile ligands in these complexes are often labile.

<span class="mw-page-title-main">Transition metal chloride complex</span> Coordination complex

In chemistry, a transition metal chloride complex is a coordination complex that consists of a transition metal coordinated to one or more chloride ligand. The class of complexes is extensive.

<span class="mw-page-title-main">Octahydrotriborate</span> Chemical compound

Octahydrotriborate is the boron hydride B3H8. It forms a variety of salts that are colorless and air-stable. The tetrabutylammonium salt is soluble in organic solvents such as acetonitrile and methylene chloride. The anion is an intermediate is the synthesis of various higher boron hydrides, such as pentaborane(9). B3H8 can be viewed as the conjugate base of triborane B3H9.

References

  1. K. Brodersen, G. Thiele, H. Gaedcke (1966). "Die Konstitution des Palladium(II)-bromids". Z. Anorg. Allg. Chem. 348 (3–4): 162–167. doi:10.1002/zaac.19663480307.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. "Information card for entry 1534319". Crystallography Open Database . 1966. Retrieved 2020-05-03.
  3. O. A. Zalevskaya, E. G. Vorob'eva1, I. A. Dvornikova and A. V. Kuchin (2008). "Palladium Complexes Based on Optically Active Terpene Derivatives of Ethylenediamine". Russian Journal of Coordination Chemistry. 34 (11): 855–857. doi:10.1134/S1070328408110110. S2CID   95529734.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Mahoney, Stuart J.; Fillion, Eric (2013). "Palladium(II) Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01617. ISBN   978-0471936237.