15278-97-4

Usage

Uses

Used in Chemical Industry:
CHLORO(TRIMETHYLPHOSPHINE)GOLD(I) is used as a catalyst for various chemical reactions, including the activation of small molecules such as carbon monoxide, carbon dioxide, and alkynes. Its ability to facilitate these reactions makes it a valuable tool in the synthesis of complex organic compounds and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, CHLORO(TRIMETHYLPHOSPHINE)GOLD(I) is used as a catalyst in the synthesis of various drugs and drug intermediates. Its unique catalytic properties enable the production of specific compounds with high selectivity and efficiency, which is crucial for the development of new and effective medications.
Used in Material Science:
CHLORO(TRIMETHYLPHOSPHINE)GOLD(I) is also employed in the field of material science, where it is used as a catalyst in the synthesis of advanced materials with unique properties. These materials can be used in various applications, such as electronics, optics, and energy storage, due to their specialized characteristics.
Used in Environmental Applications:
In environmental applications, CHLORO(TRIMETHYLPHOSPHINE)GOLD(I) is used as a catalyst to facilitate the conversion of harmful pollutants into less toxic or environmentally friendly substances. This can help in the development of greener and more sustainable chemical processes, contributing to a cleaner and healthier environment.
Overall, CHLORO(TRIMETHYLPHOSPHINE)GOLD(I) is a versatile and valuable compound with a wide range of applications across various industries, thanks to its unique chemical properties and catalytic capabilities.

InChI:InChI=1/C3H9P.Au.ClH/c1-4(2)3;;/h1-3H3;;1H/q;+1;/p-1

Upstream product

• 594-09-2 trimethylphosphane 
• 29892-37-3 chloro(dimethylsulfide) gold(I) 
• 53514-38-8 tetramethylammonium tetrachloroaurate(III) 
• 42582-73-0 cis-[(Me₃P)Au(F₃CC=CCF₃)trans-AuMe₂(PMe₃)] 
• 10294-29-8 gold(I) chloride 
• 108-90-7 chlorobenzene 
• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 
• 7647-01-0 hydrogenchloride 
• 852157-09-6 (trimethylphosphine)tris(phenylethynyl)gold(III) 

Downstream Products

• 7440-57-5 gold 
• 89989-62-8 2-phenylethynyl(trimethylphosphine)gold(I) 
• 74373-30-1 (CH₃)3PAuC₆H₄CH₃ 
• 82307-63-9 1,3-propanediylbis[(9-fluorenylidene)diphenylphosphorane]gold chloride 
• 633302-42-8 [Au(4-HCCC₆H₄CHPh)(PMe₃)] 
• 574704-46-4 (trimethylphosphine)gold(I) p-tolylthiosulfonate 
• 633302-40-6 [Au((E)-4-HCCC₆H₄CH=CHPh)(PMe₃)] 
• 159736-56-8 [W2(μ-PhCCAuPMe3)(CO)4(η-C5H5)2] 
• 159736-55-7 [Mo2(μ-PhCCAuPMe3)(CO)4(η-C5H5)2] 
• 194224-35-6 [(AuPMe3)2(μ-C(P(C6H4Me-4)3)(C5H4N-2))]ClO4 
• 852157-09-6 (trimethylphosphine)tris(phenylethynyl)gold(III) 

Relevant academic research and scientific papers

New reactivity at the silicon bridge in sila[1]ferrocenophanes

We describe two new types of reactivity involving silicon-bridged [1]ferrocenophanes. In an attempt to form a [1]ferrocenophane with a bridging silyl cation, the reaction of sila[1]ferrocenophane [Fe(η-C5H4)2Si(H)TMP] (12) (TMP = 2,2,6,6-tetramethylpiperidyl) towards the hydride-abstraction reagent trityl tetrakis(pentafluorophenyl)borate ([CPh3][B(C6F5)4]) was explored. This yielded the unusual dinuclear species [Fe(η-C5H4)2Si(TMP·H)(η-C5H3)Fe(η-C5H4)Si(H)TMP][B(C6F5)4] [13][B(C6F5)4] in low yield. The formation of [13]+ is proposed to involve abstraction of hydride from the silicon bridge in 12 with subsequent C-H bond cleavage of a cyclopentadienyl group by the resulting electrophilic transient silyl cation intermediate. We also explored the reaction of dimethylsila[1]ferrocenophane [Fe(η-C5H4)2SiMe2] (1) with the Au(i) species AuCl(PMe3). This was found to result in addition of the Au-Cl bond across the Cpipso-Si bond to yield the ring-opened species [1′-(chlorodimethylsilyl)-ferrocenyl](trimethylphosphine)gold(i), [Fe(C5H4SiMe2Cl){C5H4Au(PMe3)}] (14). This represents the first example of ring-opening addition of a metallocenophane with a reagent possessing a transition metal-halogen bond.

Vibrational and solid-state phosphorus-31 nuclear magnetic resonance spectroscopic studies of 1:1 complexes of PPh3 with gold(I) halides; crystal structure of [AuBr(PMe3)]

The crystal structure of [AuBr(PMe3)], like that of the corresponding chloride, was found to consist of three crystallographically independent molecules linked through weak Au ... Au contacts to form helical chains. The Au ... Au distances [3.648(1), 3.980(2), 3.548(2) A] are, however, significantly longer than in the chloro- and iodo-complexes, implying that the Au ... Au interaction is weakest in the bromide. The far-IR and Raman spectra of [AuX(PMe3)] (X = Cl, Br or I) have been measured, and assignments made for the bands observed. The spectra were analysed to see whether they show any effects of the weak Au ... Au bonding evident in the crystal structures. In particular, the low-wavenumber limit of previously reported Raman spectra for these species has been extended in order to search for v(Au2) bands. The X = Cl or I compounds show a strong Raman band which can be assigned to the δ(PAuX) deformation, but no v(Au2) bands were found in the region predicted on the basis of recent assignments for such modes in other complexes which display Au ... Au contacts of similar length. Possible reasons, including an interaction between v(Au2) and δ(PAuX) modes, are discussed. The solid-state cross polarization magic angle spinning 31P NMR spectra of the chloride and iodide complexes consist of doublets due to the presence of 1J(197Au-31P) coupling. This is a rare observation of spin-spin coupling between the spin I = 1/2 31P nucleus and the strongly quadrupole coupled 197Au nucleus, and permits estimation of the 1J(197Au-31P) coupling constants for these complexes.

GOLD COMPOSITIONS AND METHODS OF USE THEREOF

Gold compounds and pharmaceutically acceptable salts thereof are disclosed. Certain compounds and salts are active as antibacterial, antifungal, and/or anti-parasitic agents. The disclosure provides pharmaceutical compositions containing the gold compounds. Methods of using the gold compounds to treat bacterial infections are disclosed.

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

A theoretical DFT-based and experimental study of the transmetalation step in Au/Pd-mediated cross-coupling reactions

In this work a combined theoretical and experimental investigation of the cross-coupling reaction involving two metallic reaction centers, namely gold and palladium, is described. One metal center (Au) hereby is rather inert towards change in its oxidation state, whereas Pd undergoes oxidative insertion and reductive elimination steps. Detailed mechanistic and energetic studies of each individual step, with the focus on the key transmetalation step are presented and compared for different substrates and ligands on the catalytic Pd center. Different aryl halides (Cl, Br, I) and aryl triflates were investigated. Hereby the nature of the counteranion X turned out to be crucial. In the case of X=Cl and L=PMe3 the oxidative addition is rate-determining, whereas in the case of X=I the transmetalation step becomes rate-determining in the Au/Pd-cross-coupling mechanism. A variety of Au-Pd transmetalation reaction scenarios are discussed in detail, favoring a transition state with short intermetallic Au-Pd contacts. Furthermore, without a halide counteranion the transmetalation from gold(I) to palladium(II) is highly endothermic, which confirms our experimental findings that the coupling does not occur with aryl triflates and similar weakly coordinating counteranions - a conclusion that is essential in designing new Au-Pd catalytic cycles. In combination with experimental work, this corrects a previous report in the literature claiming a successful coupling potentially catalytic in both metals with weakly coordinating counteranions. A helping hand: For the transmetalation from gold(I) to palladium(II), halide ions play a crucial role (see scheme). Without the formation of a strong gold(I)-halogen bond (e.g., with sulfonate), the transmetalation does not proceed.

Bis(1,2,3-thiadiazole)s as precursors in the synthesis of bis(alkynethiolate)gold(I) derivatives

The cleavage of bis(1,2,3-thiadiazole)s in the presence of strong bases in situ gives bis(alkynethiolate)s, which provide bis(alkynethiolate)gold(I) derivatives with the general formula [Au2(S-C≡C-spacer- C≡C-S)L2] (L = monophosphanes; spacer = none, 1,4-C 6H4, 1,3-C6H4, 2,7-C 15H12 and 3,5-C7H7N). The dinuclear structure was confirmed by X-ray diffraction studies of the complexes (PPN) 2[Au2(S-C≡C-C≡C-S)(C6F 5)2] and [Au2{3,5-(S-C≡C) 2-C7H7N}(PPh3)2] {PPN = bis(triphenylphosphane)iminium}. The use of diphosphanes gives complexes with higher nuclearity and cyclic structures. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Preparative routes to the first tri- and tetra(alkynyl)gold(III) compounds: (L)Au(C=CR)3 and [ER4]_ [Au(C≡CR) 4]-

The preparation of tri(alkynyl)gold(III) complexes (RC≡C) 3Au(L) as metastable compounds was discussed. It was found that the complex can be prepared if a small and strong trialkylphosphine donor was introduced as an auxiliary ligand L. The complex with L = PMe3 was crystallize in a solvent-free form and as a 1:1 solvate with CH 2Cl2. The results show that the stability of polyalkynyl complexes of gold(III) centers appears to be generally lower than that of the isoelectronic platinum(II) centers.

(Fluoren-9-ylidene)methanedithiolato complexes of gold: Synthesis, luminescence, and charge-transfer adducts

Piperidinium 9H-fluorene-9-carbodithioate and its 2,7-di-tert-butyl- substituted analogue [(pipH){S2CCH(C12H6R 2-2,7)}, R = H (1a), t-Bu (1b)] and 2,7-bis(octyloxy)-9H-fluorene-9- carbodithioic acid [HS2CCH(C12H6(OC 8H17)2-2,7), 2] and its tautomer [2,7-bis(octyloxy)fluoren-9-ylidene]methanedithiol [(HS)2C=C(C 12H6(OC8H17)2-2,7), 3] were employed for the preparation of gold complexes with the (fluoren-9-ylidene)methanedithiolato ligand and its substituted analogues. The gold(I) compounds Q2[Au2{μ-K2-S,S-S 2C=C12H6R2-2,7)}2], where Q+ = PPN+ or Pr4N+ for R = H (Q24a) or Q+ = Pr4N+ for R = OC 8H17 [(Pr4N)24c], were synthesized by reacting Q[AuCl2] with 1a or 2 (1:1) and excess piperidine or diethylamine. Complexes of the type [{Au(PR′3)} 2{,u-κ2-S,S-S2C=C(C12H 6R2-2,7)}2] with R = H and R′ = Me (5a), Et (5b), Ph (5c), and Cy (5d) or R = t-Bu and R′ = Me (5e), Et (5f), Ph (5g), and Cy (5h) were obtained by reacting [AuCl(PR'3)] with 1a,b (1:2) and piperidine. The reactions of 1a,b or 2 with Q[AuCl4] (2:1) and piperidine or diethylamine gave Q[Au{κ2-S,S-S 2C=C(C12H6R2-2,7)}2] with Q+ = PPN+ for R = H [(PPN)-6a], Q+ = PPN + or Bu4N+ for R = t-Bu (Q6b), and Q + = Bu4N+ for R = OC8H17 [(Bu4N)6c]. Complexes Q6a-c reacted with excess triflic acid to give [Au{κ2-S,S-S2C=C(C12H6R 2-2,7)}{κ2-S,S-S2CCH(C12H 6R2-2,7)}] [R = H (7a), t-Bu (7b), OC8H 17 (7c)]. By reaction of (Bu4N)6b with PhlCl2 (1:1) the complex Bu4N[AuCl2{κ2-S,S- S2C= C(C12H6(t-Bu)2-2,7)}] [(Bu 4N)8b] was obtained. The dithioato complexes [Au{SC(S)CH(C 12H8)}{PCy3)] (9) and [Aun(S 2-CCH(C12H8)}n] (10) were obtained from the reactions of 1a with [AuCl(PCy3)] or [AuCl(SMe 2)], respectively (1:1), in the absence of a base. Charge-transfer adducts of general composition Q[Au{κ2-S,S-S 2C=C(C12H6R2-2,7)}2]· 1.5TCNQ·xCH2Cl2 [Q+ = PPN+, R = H, x = 0 (11a); Q+ = PPN+, R = t-Bu, x = 2 (11b); Q+ = Bu4N+, R = OC8H17, x = 0 (11c)] were obtained from Q6a-c and TCNQ (1:2). The crystal structures of 5c·THF, 5e·2/3CH2Cl2, 5g·CH 2Cl2, (PPN)6a·2Me2CO, and 11b were solved by X-ray diffraction studies. All the gold(I) complexes here described are photoluminescent at 77 K, and their emissions can be generally ascribed to LMMCT (Q24a,c, 5a-h, 10) or LMCT (9) excited states.

Mixed ligand gold(I) complexes of phosphines and thiourea and X-ray structure of (thiourea-κS)(tricyclohexylphosphine)gold(I)chloride

A series of mixed ligand gold(I) complexes with thiourea (Tu) and various phosphines, [R3PAuTu]Cl, have been prepared and characterized by elemental analysis, IR and NMR (13C, 15N and 31P) spectroscopies and X-ray crystallography. The spectral data of all complexes are consistent with the sulfur coordination of thiourea to gold(I). The single crystal X-ray structure of the complex [Cy3P-Au-Tu]Cl revealed that the geometry is not perfectly linear at the gold(I) with a P-Au-S bond angle of 168.54(9)°. The Au-P and Au-S distances are 2.274(2) and 2.295(2) A?, respectively.

Complexes of gold(I) and platinum(II) with polyaromatic phosphine ligands

Gold and platinum(II) complexes of the phosphine ligands PArnPh3-n (Ar=naphthyl, anthracenyl, ferrocenyl and other polyaromatic groups) have been synthesised. The electron donating abilities of naphthyl and anthracenyl phosphine ligands has been explored using gas phase photoelectron spectral data on the parent phosphines and their relative complexing ability to platinum precursor molecules has been assessed by means of synthetic studies and NMR experiments. Their steric parameters have been estimated by the Tolman cone angle methodology using X-ray crystallographic data. The molecular structures of the gold complexes [AuCl(PAn2Ph)]·CHCl3 and [Au(PFc2Ph)2]·CHCl3 have been determined.