15617-19-3

Basic information

• Product Name: Bis(benzonitrile)dichloroplatinum(II)
• Synonyms: DICHLOROBIS(BENZONITRILE)PLATINUM (II);CIS-BIS(BENZONITRILE)DICHLOROPLATINUM(II);BIS(BENZONITRILE)PLATINUM(II) CHLORIDE;BIS(BENZONITRILE)DICHLOROPLATINATE (II);cis-di(benzonitrile)dichloroplatinum(ii);bis(benzonitrile)dichloroplatinumpt41.3%;cis-bis(benzonitrile)platinum(II) chloride;Bis(benzonitrile)dichloroplatinum(II)
• CAS NO: 15617-19-3
• Molecular Formula: C₁₄H₁₀Cl₂N₂Pt
• Molecular Weight: 472.23
• EINECS: 238-943-7
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Platinum;chemical reaction,pharm,electronic,materials
• Mol File: 15617-19-3.mol

Chemical Properties

• Melting Point: 224 °C (dec.)(lit.)
• Boiling Point: 191.1 °C at 760 mmHg
• Flash Point: 71.7 °C
• Appearance: Pale yellow micro-crystals
• CAS DataBase Reference: Bis(benzonitrile)dichloroplatinum(II)(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(benzonitrile)dichloroplatinum(II)(15617-19-3)
• EPA Substance Registry System: Bis(benzonitrile)dichloroplatinum(II)(15617-19-3)

Safety Data

• Hazard Codes: T
• WGK Germany: 3
• RTECS: TP2185000
• Hazardous Substances Data: 15617-19-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Bis(benzonitrile)dichloroplatinum(II) is used as a catalyst for a range of chemical reactions, enhancing the efficiency and selectivity of the processes. Its applications include:
1. Asymmetric hydroformylation reactions: It acts as a catalyst to selectively produce aldehydes with a specific stereochemistry, which is crucial for the synthesis of various pharmaceuticals and fine chemicals.
2. Allylation reactions: Bis(benzonitrile)dichloroplatinum(II) facilitates the formation of carbon-carbon bonds through allylation, a significant process in the synthesis of complex organic molecules.
3. Carbene insertion into O-H bonds of alcohols: It catalyzes the insertion of carbene into the O-H bond of alcohols, leading to the formation of valuable synthetic intermediates.
4. Cyclopropanation reactions: Bis(benzonitrile)dichloroplatinum(II) aids in the cyclopropanation of alkenes, creating cyclopropane derivatives that are essential building blocks in organic chemistry.
5. Hydrosilylation reactions: It is employed as a catalyst in hydrosilylation reactions, which involve the addition of a silicon-hydrogen bond to an unsaturated carbon-carbon bond, a vital process in the synthesis of organosilicon compounds.

InChI:InChI=1/2C7H5N.2ClH.Pt/c2*8-6-7-4-2-1-3-5-7;;;/h2*1-5H;2*1H;/q;;;;+2/p-2

Upstream product

• 13869-38-0 bis(acetonitrile)dichloroplatinum(II) 
• 100-47-0 benzonitrile 
• 10025-65-7 platinum(II) chloride 
• 10025-99-7 potassium tetrachloroplatinate(II) 
• 14873-63-3 cis-bis(benzonitrile)dichloroplatinum(II) 
• 21264-32-4 diacetonitriledichloridopalladium(II) 

Downstream Products

• 864978-45-0 [1-phenyl-2,5-di(2-pyridyl)phosphole]PtCl₂ 
• 825651-71-6 [1-phenyl-2-(2-pyridyl)-5-(2-thienyl)phosphole]PtCl₂ 
• 132108-60-2 ((C₂H₅)4N)⁽¹⁺⁾*(Pt(C₆H₅CN)Cl₃)^(1-)=((C₂H₅)4N)(Pt(C₆H₅CN)Cl₃) 
• 14056-88-3 trans-dichlorobis(triphenylphosphine)platinum(II) 
• 10199-34-5 cis-dichlorobis(triphenylphosphine)platinum(II) 
• 61586-84-3 cis-dichlorobis(chlorodiphenylphosphine)platinum(II) 
• 121962-50-3 chloro{phenylbis(5,6-dimethyl-7-phenyl-7-phosphabicyclo{2.2.1}hept-5-en-2-yl)phosphine}platinum(II)* 3.5 dichloromethane 
• 1291-32-3 zirconocene dichloride 
• 10199-34-5 bis(triphenylphosphine)platinum(II) dichloride 
• 83095-83-4 [platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)] 
• 30053-58-8 cis-[PtCl₂(triphenyl phosphite)2] 
• 90667-70-2 dichloro{bis(dicyclohexylphosphino)ethane}platinum(II) 

Relevant articles and documents

Giant Concentric Metallosupramolecule with Aggregation-Induced Phosphorescent Emission

Fluorescent metallosupramolecules have received considerable attention due to their precisely controlled dimensions as well as the tunable photophysical and photochemical properties. However, phosphorescent analogues are still rare and limited to small structures with low-temperature phosphorescence. Herein, we report the self-assembly and photophysical studies of a giant, discrete metallosupramolecular concentric hexagon functionalized with six alkynylplatinum(II) bzimpy moieties. With a size larger than 10 nm and molecular weight higher than 26000 Da, the assembled terpyridine-based supramolecule displayed phosphorescent emission at room temperature. Moreover, the supramolecule exhibited enhanced aggregation-induced phosphorescent emission compared to the ligand by tuning the aggregation states through intermolecular interactions and significant enhancement of emission to CO2 gas.

Multi-nuclear NMR investigation of nickel(II), palladium(II), platinum(II) and ruthenium(II) complexes of an asymmetrical ditertiary phosphine

Complexes synthesized by reacting alkyl and aryl phosphines with different transition metals are of great interest due to their catalytic properties. Many of the phosphine complexes are soluble in polar solvents as a result they find applications in homogeneous catalysis. In our present work we report, four transition metal complexes of Ni(II), Pd(II), Pt(II) and Ru(II) with an asymmetrical ditertiaryphosphine ligand. The synthesized ligand bears a less electronegative substituent such as methyl group on the aromatic nucleus hence makes it a strong ω-donor to form stable complexes and thus could effectively used in catalytic reactions. The complexes have been completely characterized by elemental analyses, FTIR, 1HNMR, 31PNMR and FAB Mass Spectrometry methods. Based on the spectroscopic evidences it has been confirmed that Ni(II), Pd(II) and Pt(II) complexes with the ditertiaryphosphine ligand showed cis whereas the Ru(II) complex showed trans geometry in their molecular structure.

Synthesis and properties of new phosphorescent red light-excitable platinum(II) and palladium(II) complexes with schiff bases for oxygen sensing and triplet-triplet annihilation-based upconversion

New Pt(II) and Pd(II) complexes with donor-acceptor Schiff bases are conveniently prepared in only two steps. The complexes efficiently absorb in the red part of the spectrum (ε > 105 M-1 cm -1) and show moderate to strong

A parahydrogen based NMR study of Pt catalysed alkyne hydrogenation

A parahydrogen based NMR study of the platinum(ii) bis-phosphine triflate catalysed hydrogenation of alkynes in methanol reveals that platinum bis-phosphine alkyl cations and methanol functionalised platinum bis-phosphine alkylether cations, are responsible for the observed alkene and vinylether products.

Novel tailoring reaction for two adjacent coordinated nitriles giving platinum 1,3,5-triazapentadiene complexes

The tailoring reaction of the two adjacent nitrile ligands in cis-[PtCl2(RCN)2] (R = Me, Et, CH2Ph, Ph) and [Pt(tmeda)(EtCN)2][SO3CF3]2 (8·(OTf)2; tmeda = N,N,N′,N′- tetramethylethylenediamine) upon their interplay with N,N′- diphenylguanidine (DPG; NH=C(NHPh)2), in a 1:2 molar ratio gives the 1,3,5-triazapentadiene complexes [PtCl2{NHC(R)NHC(R)=NH}] (1-4) and [Pt(tmeda){NHC(Et)NHC(Et)NH}][SO3CF3]2 (10·(OTf)2), respectively. In contrast to the reaction of 8·(OTf)2 with NH=C(NHPh)2, interaction of 8·(OTf)2 with excess gaseous NH3 leads to formation of the platinum(II) bis(amidine) complex cis-[Pt(tmeda){NH=C(NH 2)Et}2][SO3CF3]2 (9·(OTf)2). Treatment of trans-[PtCl2(RCN) 2] (R = Et, CH2Ph, Ph) with 2 equiv of NH=C(NHPh) 2 in EtCN (R = Et) and CH2Cl2 (R = CH 2Ph, Ph) solutions at 20-25°C leads to [PtCl{NH=C(R)NC(NHPh)=NPh} (RCN)] (11-13). When any of the trans-[PtCl2(RCN)2] (R = Et, CH2Ph, Ph) complexes reacts in the corresponding nitrile RCN with 4 equiv of DPG at prolonged reaction time (75°C, 1-2 days), complexes containing two bidentate 1,3,5-triazapentadiene ligands, i.e. [Pt{NH=C(R)NC(NHPh)=NPh}2] (14-16), are formed. Complexes 14-16 exhibit strong phosphorescence in the solid state, with quantum yields (peak wavelengths) of 0.39 (530 nm), 0.61 (460 nm), and 0.74 (530 nm), respectively. The formulation of the obtained complexes was supported by satisfactory C, H, and N elemental analyses, in agreement with FAB-MS, ESI-MS, IR, and 1H and 13C{1H} NMR spectra. The structures of 1, 2, 4, 11, 13, 14, 9· (picrate)2, and 10·(picrate) 2 were determined by single-crystal X-ray diffraction.

Synthesis and characterisation of mixed ligand Pt(ii) and Pt(iv) oxadiazoline complexes

The nitrile ligands in trans-[PtX2(PhCN)2] (X = Cl, Br, I) undergo sequential 1,3 dipolar cycloadditions with nitrones R 1R2C=N+(Me)-O- (R1 = H, R2 = Ph; R1 = CO2Et, R2 = CH 2CO2Et) to selectively form the Δ4-1,2,4- oxadiazoline complexes trans-[PtX2(PhCN) {N=C(Ph)-O-N(Me)-CR 1R2}] or trans-[PtX2{N=C(Ph)-O-N(Me)-CR 1R2}2] in high yields. The reactivity of the mixed ligand complexes trans-[PtX2(PhCN){N=C(Ph)-O-N(Me)-CR 1R2}] towards oxidation and ligand substitution was studied in more detail. Oxidation with Cl2 or Br2 provides the Pt(iv) species trans-[PtX2Y2(PhCN){N=C(Ph)-O-N(Me)- CH(Ph)}] (X, Y = Cl, Br). The mixed halide complex (X = Cl, Y = Br) undergoes halide scrambling in solution to form trans-[PtX(4-n)Y n(PhCN){N=C(Ph)-O-N(Me)-CH(Ph)}] as a statistical mixture. Ligand substitution in trans-[PtCl2(PhCN){N=C(Ph)-O-N(Me)-CR 1R2}] allows for selective replacement of the coordinated nitrile by nitrogen heterocycles such as pyridine, DMAP or 1-benzyl-2- methylimidazole to produce mixed ligand Pt(ii) complexes of the type trans- [PtX2(heterocycle){N=C(Ph)-O-N(Me)-CR1R2}]. All compounds were characterised by elemental analysis, mass spectrometry, IR and 1H, 13C and 195Pt NMR spectroscopy. Single-crystal X-ray structural analysis of (R,S)-trans-[PtBr 2{N=C(Ph)-O-N(Me)-CH(Ph)}2] and trans-[PtCl 2(C5H5N){N=C(Ph)-O-N(Me)-CH(Ph)}] confirms the molecular structure and the trans configuration of the heterocycles relative to each other. The Royal Society of Chemistry.

Nucleophilic addition of bifunctional sulfimidosulfides to platinum(IV)-coordinated nitriles

Reactions of the platinum(IV) nitrile complexes [PtCl4(RCN) 2] (R = Me, CH2Ph, Ph) with 1,2- and 1,4-PhS(=NH)C 6H4SPh in CH2Cl2 afforded addition products of sulfimides and coordinated nitriles, viz., the [PtCl 4{NH=C(R)N=S(Ph)(C6H4SPh)}2] complexes. The latter were isolated in 75-90% yielks and characterized by elemental analysis, positive-ion FAB mass spectrometry, IR spectroscopy, and 1H and 13C1H NMR spectroscopy. The temperature dependence of the 1H NMR spectra of the model [PtCl 4{NH=C(R)N=SPh2}2] complexes (R = Me, Et) in CD2Cl2 studied in a temperature range from +40 to -70°C demonstrated that E-Z isomerization of the ligands is a dynamic process in a range from +40 to -10°C. The activation free energy of this process was calculated.

Ligand discrimination in the reaction of nitrones with [PtCl2(PhCN)2]. Selective formation of mono-oxadiazoline and mixed bis-oxadiazoline complexes under thermal and microwave conditions

[2+3] Cycloaddition of nitrones to the nitrile ligands in the complexes cis- or trans-[PtCl2(PhCN)2] occurs under ligand differentiation and allows for selective synthesis of complexes of the type cis- or trans-[PtCl2(oxadiazoline)-(PhCN)]. Microwave irradiation enhances the reaction rates of the cycloaddition considerably and further favours the selectivity towards the mono-cycloadduct with respect to thermal conditions, because the first cycloaddition is accelerated to a higher extent than the second one. Reaction of the trans-substituted mono-oxadiazoline complexes with a nitrone different from the one used for the first cycloaddition step gives access to mixed bis-oxadiazoline compounds of the composition trans-[PtCl2(oxadiazoline-a)(oxadiazoline-b)]. The corresponding cis-configured complexes, however, do not undergo further cycloaddition. All reactions described occur without isomerisation of the stereochemistry around the platinum center, independently of whether thermal or microwave heating is applied.

1,1-Ethylenedithiolato complexes of palladium(II) and platinum(II) with isocyanide and carbene ligands

The reactions of [Tl2{S2C=C{C(O)Me}2}]n with [MCl2(NCPh)2] and CNR (1:1:2) give complexes [M{η2-S2C= C{C(O)Me}2}(CNR)2] [R = tBu, M = Pd (1a), Pt (1b); R = C6H3Me2-2,6 (Xy), M = Pd (2a), Pt (2b)]. Compound 1b reacts with AgClO4 (1:1) to give [{Pt(CNtBu)2}2Ag2 {μ2,η2-(S,S′)-{S2C=C{C(O) Me}2}2}](ClO4)2 (3). The reactions of 1 or 2 with diethylamine give mixed isocyanide carbene complexes [M{η2-S2C=C{C(O)Me}2}(CNR)-{C (NEt2)(NHR)}] [R = tBu, M = Pd (4a), Pt (4b); R = Xy, M = Pd (5a), Pt (5b)] regardless of the molar ratic of the reagents. The same complexes react with an excess of ammonia to give [M{η2-(S,S′)-S2C=C{C(O)Me}2}- (CNtBu){C(NH2)(NHtBu)}] [M = Pd (6a), Pt (6b)] or [M{η2-(S,S′)-S2C=C{C(O)Me}2}{C (NH2)(NHXy)}2] [M = Pd (7a), Pt (7b)] probably depending on steric factors. The crystal structures of 2b, 4a, and 4b have been determined. Compounds 4a and 4b are isostructural. They all display distorted square planar metal environments and chelating planar E,Z-2,2-diacetyl-1,1-ethylenedithiolato ligands that coordinate through the sulfur atoms.

Synthesis and structure of nickel(I) and platinum(I) hydride dimers having identical ancillary ligands

The preparation and structures of two new dinuclear hydrides are reported. Reaction of KBEt3H with the nickel(II) precursor Ni(dippp)Cl2 (dippp = 1,3 bis(diisopropylphosphino)propane) leads to the formation of the dinuclear complex [(dippp)Ni]2(μ-H)2. The single crystal X-ray structure of this Ni(I) dimer shows that the hydrides are symmetrically bridging with the two Ni(dippp) planes staggered with respect to each other by an angle of 75°. The corresponding reaction of KBEt3H with the platinum(II) precursor Pt(dippp)I2 leads to the formation of the dinuclear complex [(dippp)PtH]2. The single crystal X-ray structure of this Pt(I) dimer shows that the hydrides are terminal with the corresponding Pt(dippp) planes orthogonal (92.3°) to each other. The structures of these two Group 10 hydride dimers are compared to the known Pd(I) dimer [(dippp)Pd]2(μ-H)2. Crystal data: [(dippp)Ni]2(μ-H)2 (1) (C30H70Ni2P4), monoclinic, a = 11.513(2), b = 16.420(3), c = 19.696(4) A?, β = 92.40(2)°, Z=4, space group C2lc; [(dippp)PtH]2 (5) (C30H70P4Pt2), triclinic, a = 11.529(1), b = 16.581(1), c = 11.018(2) A?, α = 91.11(1), β = 107.10(1), γ = 106.166(8)°, Z=2, space group P1?. The structures were solved by Patterson and direct methods and were refined by full-matrix least-squares procedures to R = 0.0503 and 0.042 (Rw = 0.0565 and 0.038) for 2487 and 6189 reflections, respectively.