49763-41-9

Basic information

• Product Name: Chloro(tricyclohexylphosphine)gold(I)
• Synonyms: Chloro(tricyclohexylphosphine)gold(I)
• CAS NO: 49763-41-9
• Molecular Formula: C₁₈H₃₃AuClP
• Molecular Weight: 512
• Mol File: 49763-41-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 218-222°C
• Appearance: /
• CAS DataBase Reference: Chloro(tricyclohexylphosphine)gold(I)(CAS DataBase Reference)
• NIST Chemistry Reference: Chloro(tricyclohexylphosphine)gold(I)(49763-41-9)
• EPA Substance Registry System: Chloro(tricyclohexylphosphine)gold(I)(49763-41-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26-45
• WGK Germany: 3
• Hazardous Substances Data: 49763-41-9(Hazardous Substances Data)

Usage

Description

Chloro(tricyclohexylphosphine)gold(I) is a gold(I) complex with the chemical formula [AuCl(PCy3)], where Cy represents cyclohexyl. It is a coordination compound that features a gold(I) center coordinated to a chloride ligand and a tricyclohexylphosphine ligand. Chloro(tricyclohexylphosphine)gold(I) is known for its catalytic properties and is widely used in various chemical reactions.

Uses

Used in Chemical Synthesis:
Chloro(tricyclohexylphosphine)gold(I) is used as a catalyst for a variety of chemical reactions, facilitating the formation of new chemical bonds and improving the efficiency of the processes.
Used in Formal Tandem Bicyclizations:
In the field of organic chemistry, Chloro(tricyclohexylphosphine)gold(I) is used as a catalyst for formal tandem bicyclizations of styrylindoles with alkynyl alkenones. This application allows for the formation of complex molecular structures with potential applications in pharmaceuticals and materials science.
Used in Addition of X-H Bonds to Carbon-Carbon Multiple Bonds:
Chloro(tricyclohexylphosphine)gold(I) is employed as a catalyst in the addition of X-H bonds (where X can be a variety of atoms or groups) to carbon-carbon multiple bonds, such as alkenes and alkynes. This reaction type is crucial for the synthesis of various organic compounds and materials.
Used in Arylation of Pyrazine or Pyridine:
In the pharmaceutical industry, Chloro(tricyclohexylphosphine)gold(I) is used as a catalyst for the arylation of pyrazine or pyridine with aryl bromides. This reaction is essential for the synthesis of various heterocyclic compounds with potential applications as pharmaceuticals and agrochemicals.
Used in Hydroarylation of Alkenes with Indoles:
Chloro(tricyclohexylphosphine)gold(I) is utilized as a catalyst in the hydroarylation of alkenes with indoles, a reaction that is important for the synthesis of indole-containing compounds, which are often found in natural products and pharmaceuticals.
Used in Cyclization:
In the field of organic synthesis, Chloro(tricyclohexylphosphine)gold(I) is used as a catalyst for cyclization reactions, which involve the formation of a ring structure in a molecule. This type of reaction is essential for the synthesis of various cyclic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Hydroamination:
Chloro(tricyclohexylphosphine)gold(I) is employed as a catalyst in hydroamination reactions, which involve the addition of an amine group to a carbon-carbon multiple bond. This reaction is important for the synthesis of various amine-containing compounds, which are often found in pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 98938-44-4 5.6-μ-(AuPCy3)-nido-B10H13 
• 29892-37-3 chloro(dimethylsulfide) gold(I) 
• 2622-14-2 tricyclohexylphosphine 
• 932-72-9 (Dichloroiodo)benzene 
• 64-17-5 ethanol 
• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 
• 1190715-83-3 [AuCl₃(P(C₆H₁₁)3)] 
• 7647-01-0 hydrogenchloride 
• 7440-57-5 gold 

Downstream Products

• 199167-49-2 Au(-C*C-SiMe₃)(PCy₃) 
• 408495-43-2 [(tricyclohexylphosphine)Au](μ-CC-1,4-C6H4CC) 
• 63632-53-1 (benzenesulphinato)(tricyclohexylphosphine)gold(I) 
• 49763-42-0 (tricyclohexylphosphine)gold(I) bromide 
• 1231960-32-9 Cy₃PAu-CC-(CH=CH)2-CC-AuPCy₃ 
• 1231960-33-0 Cy₃PAu-CC-(CH=CH)3-CC-AuPCy₃ 
• 1231960-36-3 Cy₃PAu-CC-1,2-di(2-methylthien-3-yl)hexafluorocyclopentene-CC-AuPCy₃ 
• 1231960-34-1 Cy₃PAu-CC-1,2-di(2-methylthien-3-yl)cyclopentene-CC-AuPCy₃ 
• 1231960-31-8 Cy₃PAu-CC-(CH=CH)-CC-AuPCy₃ 
• 49788-62-7 [AuBr₃(P(C₆H₁₁)3)] 
• 1449232-48-7 C₃₀H₄₀AuO₃P 

Relevant articles and documents

Dinuclear Au(I), Au(II) and Au(III) Complexes with (CF2)n Chains: Insights into The Role of Aurophilic Interactions in the Au(I) Oxidation

New dinuclear Au(I), Au(II) and Au(III) complexes containing (CF2)n bridging chains were obtained. Metallomacrocycles [Au2{μ-(CF2)4}{μ-diphosphine}] show an uncommon figure-eight structure, the helicity inversion barrier of which is influenced by aurophilic interactions and steric constraints imposed by the diphosphine. Halogenation of LAu(CF2)4AuL (L=PPh3, PMe3, (dppf)1/2, (binap)1/2) gave [Au(II)]2 species, some of which display unprecedented folded structures with Au?Au bonds. Aurophilic interactions facilitate this oxidation process by preorganizing the starting [Au(I)]2 complexes and lowering its redox potential. The obtained [Au(II)]2 complexes undergo thermal or photochemical elimination of R3PAuX to give Au(III) perfluorinated auracycles. Evidence of a radical mechanism for these decomposition reactions was obtained.

The leaving group in Au(i)-phosphine compounds dictates cytotoxic pathways in CEM leukemia cells and reactivity towards a Cys2His2model zinc finger

Gold(i)-phosphine auranofin-like compounds have been extensively explored as anticancer agents in the past decade. Although potent cytotoxic agents, the lack of selectivity towards tumorigenic vs. non-tumorigenic cell lines often hinders further application. Here we explore the cytotoxic effects of a series of (R3P)AuL compounds, evaluating both the effect of the basicity and bulkiness of the carrier phosphine (R = Et or Cy), and the leaving group L (Cl-vs. dmap). [Au(dmap)(Et3P)]+ had an IC50 of 0.32 μM against the CEM cell line, with good selectivity in relation to HUVEC. Flow cytometry indicates reduced G1 population and slight accumulation in G2, as opposed to auranofin, which induces a high population of cells with fragmented DNA. Protein expression profile sets [Au(dmap)(Et3P)]+ further apart from auranofin, with proteolytic degradation of caspase-3 and poly(ADP-ribose)-polymerase (PARP), DNA strand-break induced phosphorylation of Chk2 Thr68 and increased p53 ser15 phosphorylation. The cytoxicity and observable biological effects correlate directly with the reactivity trend observed when using the series of gold(i)-phosphine compounds for targeting a model zinc finger, Sp1 ZnF3.

C(sp2)-C(sp2) Reductive Elimination from Well-Defined Diarylgold(III) Complexes

A series of well-defined phosphine-ligated diarylgold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)] were prepared, and detailed kinetics of the C(sp2)-C(sp2) reductive elimination from these complexes were studied. The mechanism of the reductive elimination from the complexes cis-[Au(L)(ArF)(Ar′)(Cl)] was further studied by theoretical calculations. The combination of experimental and theoretical results suggests that the biaryl reductive elimination from organogold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)] proceeds through a concerted biaryl-forming pathway from the four-coordinated Au(III) metal center. These studies also disclose that the steric hindrance of the phosphine ligands plays a major role in promoting the biaryl-forming reductive elimination from diarylgold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)], while electronic properties of these ligands have a much smaller effect. Futhermore, it was found that the complexes with more weakly electron withdrawing aryl ligands undergo reductive elimination more quickly and the elimination rate is not sensitive to the polarity of the solvents.