14873-63-3

Basic information

• Product Name: Bis(benzonitrile)dichloroplatinum(II)
• Synonyms: bis(Benzonitrile)dichloroplatinum;DICHLOROBIS(BENZONITRILE)PLATINUM (II);CIS-BIS(BENZONITRILE)DICHLOROPLATINUM(II);BIS(BENZONITRILE)DICHLOROPLATINATE (II);BIS(BENZONITRILE)DICHLOROPLATINUM(II);BIS(BENZONITRILE)PLATINUM(II) CHLORIDE;Dichlorobis(benzonitrile)platinum(II),99%;Dichlorobis-(benzonitrilo)-platinum
• CAS NO: 14873-63-3
• Molecular Formula: C₁₄H₁₀Cl₂N₂Pt
• Molecular Weight: 472.23
• EINECS: 238-943-7
• Product Categories: organometallic complexes;Pt
• Mol File: 14873-63-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 224 °C (dec.)(lit.)
• Boiling Point: 191.1 °C at 760 mmHg
• Flash Point: 71.7 °C
• Appearance: yellow to orange/crystal
• Vapor Pressure: 0.524mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Slightly soluble in acetone, chloroform
• CAS DataBase Reference: Bis(benzonitrile)dichloroplatinum(II)(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(benzonitrile)dichloroplatinum(II)(14873-63-3)
• EPA Substance Registry System: Bis(benzonitrile)dichloroplatinum(II)(14873-63-3)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: UN3439
• WGK Germany: 3
• RTECS: TP2185000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 14873-63-3(Hazardous Substances Data)

Usage

Description

Bis(benzonitrile)dichloroplatinum(II), also known as cisplatin, is a platinum-based chemotherapy drug that has been widely used in the treatment of various types of cancer. It is a coordination complex with two benzonitrile ligands and two chloride ligands. Cisplatin works by forming covalent bonds with the purine bases of DNA, causing DNA damage and inhibiting cell replication, ultimately leading to cell death.

Uses

Used in Pharmaceutical Industry:
Bis(benzonitrile)dichloroplatinum(II) is used as an anticancer agent for the treatment of various types of cancer, including testicular, bladder, ovarian, and lung cancers. It is particularly effective against solid tumors and has been a cornerstone of chemotherapy regimens for decades.
Additionally, Bis(benzonitrile)dichloroplatinum(II) is used as a catalyst in the chemical industry for various reactions, such as:
1. Asymmetric Hydroformylation Reactions:
Bis(benzonitrile)dichloroplatinum(II) is used as a catalyst to produce aldehydes with high enantioselectivity, which are important building blocks for pharmaceuticals and fine chemicals.
2. Allylic Reactions:
It is used as a catalyst in allylation reactions, which involve the formation of carbon-carbon bonds and are crucial for the synthesis of complex organic molecules.
3. Cyclopropanation Reactions:
Bis(benzonitrile)dichloroplatinum(II) is used as a catalyst in cyclopropanation reactions, which are important for the synthesis of cyclopropane-containing compounds with potential applications in pharmaceuticals and agrochemicals.
4. Hydrosilylation Reactions:
It is used as a catalyst in hydrosilylation reactions, which involve the addition of a silicon-hydrogen bond to an unsaturated carbon-carbon bond, leading to the formation of new carbon-silicon bonds. These reactions are useful for the synthesis of organosilicon compounds with applications in materials science and the pharmaceutical industry.
5. Carbene Insertion into O-H Bonds of Alcohols:
Bis(benzonitrile)dichloroplatinum(II) is used as a catalyst in the insertion of carbenes into the O-H bonds of alcohols, which is an important method for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.

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 
• 13965-91-8 tetrachloroplatinum(II) 
• 10025-99-7 potassium tetrachloroplatinate(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) 
• 98651-98-0 cis-(Vy₂PhP)2platinum(II)Cl₂ 
• 124356-97-4 PtCl₂(P(OC₂H₅)2(OC₆H₄CH₃))2 

Relevant articles and documents

The Isolation, Characterization, and Isomerization of cis- and trans-Bis(benzonitrile)dichloroplatinum(II)

The reaction of platinum(II) chloride with neat benzonitrile gave bis(benzonitrile)dichloroplatinum(II) as a mixture of cis and trans isomers in variable proportions, depending on the temperature.The geometry of the chromatographically separated isomers was identified on the basis of the dipole-moment and IR data.The 13C NMR spectra in CDCl3 also enabled us to discriminate between isomers in both chemical shift and coupling to the 195Pt of the cyanide carbon, the resonance peak of which was utilized to follow the isomerization.The rate constant (kc) for the cis-to-trans isomerization was found to be (3.8 +/- 0.3) * 10-6 s-1 in CDCl3 at 25 deg C, ten times larger than that t = (2.9 +/- 0.2) * 10-7 s-1> of the reverse reaction.The equilibrium between cis and trans strongly favored trans in CDCl3 at 25 deg C, whereas in benzonitrile the cis form was the dominant species at room temperature, while the trans form was dominant at higher temperatures.

Periodic trends in electrode-chemisorbate bonding: Benzonitrile on platinum-group and other noble metals as probed by surface-enhanced Raman spectroscopy combined with Density Functional Theory

Detailed intramolecular vibrational spectra obtained by means of surface-enhanced Raman scattering (SERS) for benzonitrile adsorbed on seven electrode surfaces-four Pt-group metals (platinum, palladium, rhodium, and iridium) and the Group IB metals (coppe

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.

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.