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Bis(acetonitrile)dichloropalladium(II), also known as Pd(MeCN)2Cl2, is a versatile palladium(II) catalyst used in various organic transformations, including C-H activation, cross-coupling, and oxidative functionalization reactions. It serves as a key precursor in palladium-catalyzed processes such as decarboxylative C-H arylation of indoles and aerobic dialkoxylation of styrenes, demonstrating high reactivity and selectivity. Its stability and solubility in organic solvents make it a practical choice for catalytic applications in synthetic chemistry.

14592-56-4

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14592-56-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 14592-56-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,9 and 2 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14592-56:
(7*1)+(6*4)+(5*5)+(4*9)+(3*2)+(2*5)+(1*6)=114
114 % 10 = 4
So 14592-56-4 is a valid CAS Registry Number.
InChI:InChI=1/2C2Cl2N.Pd/c2*3-2(4)1-5;/rC4Cl4N2Pd/c5-3(6,1-9)11-4(7,8)2-10

14592-56-4 Well-known Company Product Price

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  • TCI America

  • (B1676)  Bis(acetonitrile)palladium(II) Dichloride  >98.0%(T)

  • 14592-56-4

  • 1g

  • 740.00CNY

  • Detail
  • TCI America

  • (B1676)  Bis(acetonitrile)palladium(II) Dichloride  >98.0%(T)

  • 14592-56-4

  • 5g

  • 2,620.00CNY

  • Detail
  • Alfa Aesar

  • (10002)  Bis(acetonitrile)dichloropalladium(II), Pd 40.5%   

  • 14592-56-4

  • 1g

  • 743.0CNY

  • Detail
  • Alfa Aesar

  • (10002)  Bis(acetonitrile)dichloropalladium(II), Pd 40.5%   

  • 14592-56-4

  • 5g

  • 2826.0CNY

  • Detail
  • Aldrich

  • (225657)  Bis(acetonitrile)dichloropalladium(II)  99%

  • 14592-56-4

  • 225657-500MG

  • 532.35CNY

  • Detail
  • Aldrich

  • (225657)  Bis(acetonitrile)dichloropalladium(II)  99%

  • 14592-56-4

  • 225657-5G

  • 2,937.87CNY

  • Detail

14592-56-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(acetonitrile)dichloropalladium(II)

1.2 Other means of identification

Product number -
Other names Dichlorobis(acetonitrile)palladium(II)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14592-56-4 SDS

14592-56-4Relevant articles and documents

N, N′-Olefin functionalized Bis-Imidazolium Pd(II) chloride N-Heterocyclic carbene complex builds a supramolecular framework and shows catalytic efficacy for 'C-C' coupling reactions

Roymahapatra, Gourisankar,Samanta, Tapastaru,Seth, Saikat Kumar,Mahapatra, Ambikesh,Chattopadhyay, Shyamal Kumar,Dinda, Joydev

, p. 1057 - 1065 (2015)

The ligand 3,3′-(p-phenylenedimethylene)bis{1-(2-methylallyl)} imidazolium bromide (1) and its Palladium(II) N-heterocyclic carbene (NHC) complex (3) has been synthesized and characterized by several spectroscopic techniques and the solid-state structure of 3 has been determined by single crystal X-ray diffraction studies. The Pd(II) complex possesses ring head to tail π- π stacking interactions (3.767 A ) through imidazole rings. Complex 3 catalyzes Suzuki-Miyaura 'C-C' coupling reaction. DFT calculations have been used to understand the HOMO/LUMO energy and hence the stability and reactivity of Pd(II) complex in syn and anti-configuration.

Palladium(II) chloro complexes with (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol

Khisamutdinov,Shitikova,Anpilogova,Golubyatnikova,Mulagaleev,Murinov

, p. 638 - 646 (2015)

Palladium(II) chloro complexes with (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-tria-zol-1-ylmethyl)pentan-3-ol (L), such as trans-[PdCl2L2], cis-[PdCl2L2], and trans-[Pd2(μ-Cl)2Cl2L2], were synthesized. The structures of their coordination cores and the coordination modes of the reagent to the metal ion via the N(4) atom of the triazole ring were established by electronic, IR, and 1H and 13C NMR spectroscopy. The ratio of RS- and RR(SS)-diastereomers in the complexes was determined from the complete assignment of signals in their 1H and 13C NMR spectra.

Structure of Cu(II) and Pd(II) complexes with 2-(2,2-dimethylhydrazone)pentanone-4

Kuratieva,Vikulova,Shushanyan,Nikolaeva,Dorovskikh,Mikhaleva,Morozova

, p. 1004 - 1008 (2017)

Palladium(II) and copper(II) complexes with 2-(2,2-dimethylhydrazone) pentanone-4 are synthesized for the first time. The compounds are characterized by IR and NMR spectroscopy, elemental and single crystal X-ray diffraction analyses. The palladium complex crystallizes in the space group I41/a; the copper complex crystallizes in the space group P1?. Both compounds are molecular; the palladium chelate core has a distorted square geometry and that of copper has a distorted tetrahedral geometry. The average M–O and M–N bond lengths are respectively 1.9808(15) ? and 2.0427(17) ? for M = Pd, 1.915(8) ? and 1.97(1) ? for M = Cu. The chelate O–M–N angles are 88.32(7)-91.67(7)° for M = Pd, 93.37(4)-99.02(5)° for M = Cu.

Classical and non-classical redox reactions of Pd(ii) complexes containing redox-active ligands

Sanz, Corey A.,Ferguson, Michael J.,McDonald, Robert,Patrick, Brian O.,Hicks, Robin G.

, p. 11676 - 11678 (2014)

Reactivity studies of a Pd(ii)-verdazyl complex reveal novel ligand-centred reduction processes which trigger pseudo-reductive elimination at Pd. Reaction of the complex with water induces a ligand-centred redox disproportionation. The reduced verdazyl ligands can also be reversibly protonated. This journal is

Photolysis of tetraphenylcyclobutadiene palladium chloride induced by LMCT excitation

Kunkely, Horst,Vogler, Arnd

, p. 248 - 250 (2006)

The complex tetraphenylcyclobutadiene palladium(IV) chloride shows a longest-wavelength absorption at λmax = 530 nm which is assigned to a LMCT transition from the C4Ph4 dianion to Pd(IV). LMCT excitation leads to the release of Pd(CH3CN) 2Cl2 and neutral C4Ph4 which dimerizes to octaphenylcyclooctatetraene.

STUDY ON THE MECHANISM OF ETHYLENE OXIDATION BY A NITRITE COMPLEX OF PALLADIUM IN CHLOROFORM MEDIUM.

Gusevskaya,Beck,Stepanov,Likholobov,Nekipelov,Yermakov,Zamaraev

, p. 177 - 188 (1986)

A detailed mechanism of ethylene oxidation by a palladium nitrite complex Pd(NO//2)Cl(CH//3CN)//2 in chloroform solution is studied using IR and **1H NMR spectroscopy. Kinetic and spectral data obtained indicate the formation of a number of intermediates. The structure and routes of decomposition of the intermediates to end products are suggested.

Flexible cofacial binuclear metal complexes derived from α,α-bis(salicylimino)-m-xylene

Maverick, Andrew W.,Laxman, Ravi K.,Hawkins, Mark A.,Martone, Daniel P.,Fronczek, Frank R.

, p. 200 - 206 (2005)

The tetradentate Schiff-base ligand SIXH2 (α,α-bis(salicylimino)-m-xylene), prepared from salicylaldehyde and m-xylylenediamine, forms cofacial binuclear complexes with Pd and Cu. Of the two isomers possible (trans-syn and trans-anti) for M2(SIX) 2, these complexes crystallize exclusively as the trans-anti isomer. In ansolvous Pd2(SIX)2, the metal-containing planes are approximately parallel, with Pd ... Pd 4.416(1) A. Pd 2(SIX)2 also forms a crystalline solvate, in which the molecules adopt a more open conformation with longer metal-metal distances (5.109(1) and 5.112(1) A). The M ... M distance is significantly longer in Cu2(SIX)2 (6.653(1) A), because of conformational changes in the m-xylylene moieties and substantial tetrahedral distortion about Cu.

N-donor complexes of palladium as catalysts for Suzuki cross-coupling reactions in ionic liquids

Mathews, Christopher J.,Smith, Paul J.,Welton, Tom

, p. 27 - 32 (2004)

Palladium imidazole complexes have been used as catalyst precursors for the Suzuki cross-coupling reaction in 1-butyl-3-methylimidazolium-based ambient temperature ionic liquids. The system provides a stable, recyclable method for iodo- and bromoarenes. The preferred reaction conditions are explored and the effect of changing the ionic liquid components is investigated.

Trimeric cage complexes of platinum group and coin metals

Stickel, Marc,Maichle-Moessmer, Caecilia,Mayer, Hermann A.

, p. 518 - 525 (2014)

The treatment of cis,cis-1,3,5-tris(diphenylphosphinomethyl)cyclohexane (tdppmcy) with Rh(CO)Cl(PPh3)2, MCl2L 2 (M = Pd, Pt; L = PhCN, MeCN), Pt(CN)2, AgBF4, or Au(Cl)PPh3 in a stoichiometric ratio of 2:3 affords the trimeric macrocyclic cage compounds [M]3(tdppmcy)2 {[M] = trans-Rh(CO)Cl (2), trans-PdCl2 (3), trans-Pt(CN)2 (4b), Ag+ (5), and AuCl (6)} in good yields. Only when PtCl 2(PhCN)2 was used as complex precursor, the formation of coordination polymers was observed. NMR spectroscopy in solution as well as single-crystal X-ray diffraction analyses demonstrate that in all cases two tdppmcy ligands coordinate three metal fragments exclusively in trans fashion. Copyright

A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

Luu, Hieu-Trinh,Wiesler, Stefan,Frey, Georg,Streuff, Jan

, p. 2478 - 2481 (2015)

A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxyerythratidinone. (Figure Presented).

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