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Usage

Uses

Used in Agriculture:
Fentin hydroxide is used as a fungicide for controlling a variety of infections in crops, such as blight on potatoes, leaf spot on sugar beet, and alternaria blight on carrots. Its effectiveness in combating fungal infections makes it a valuable asset in agricultural practices.
Used in Insect Control:
Fentin hydroxide is also used as an antifeeding compound for insect control. By discouraging insects from feeding on treated plants, it helps protect crops from damage and reduces the need for additional pesticide applications.
Used in Chemical Synthesis:
Fentin hydroxide serves as a reactant in transmetalation reactions with Ir clusters and is involved in the synthesis of various compounds with potential applications. Some of these include (E)-(Nitrophenyl)propenoic acid organotin(IV) carboxylates with antitumor activity, triorganotin chrysanthemumates for larvicidal studies, polynuclear organotin(IV) carboxylates containing ferrocenyl moieties for antitumor investigation, organotin(IV) aminophenylacrylate complexes, and 4-Biphenylcarboxylic acid derivatives for in vitro cytotoxicity studies.

Reactivity Profile

Fentin hydroxide is sensitive to temperatures above 113°F and prolonged exposure to light. Incompatible with strongly acidic compounds. Also incompatible with oils used in oil spray formulations .

Fire Hazard

Flash point data for Fentin hydroxide are not available; however, Fentin hydroxide is probably combustible.

Biochem/physiol Actions

Keratin 19 (KRT19) is a type I cytokeratin involved in the formation of intermediate filaments in other cells. It is also involved in the myofiber organization. It is localized at the costameres of striated muscle. KRT19 serves as a connector between contractile apparatus and dystrophin at the costamere of striated muscle. It has been postulated that KRT19 can bind directly with the N-terminal actin-binding domain of dystrophin, neurofilaments, vimentin and plectin. It also functions as a biomarker for the diagnosis of endometriosis.

Purification Methods

West, Baney and Powell [J Am Chem Soc 82 6269 1960] purified a sample which was grossly contaminated with tetraphenyltin and diphenyltin oxide by dissolving it in EtOH, most of the impurities remaining behind as an insoluble residue. Evaporation of the EtOH extract gave the crude hydroxide which was converted to triphenyltin chloride (above) by grinding in a mortar under 12M HCl, then evaporating the acidic solution. The chloride, after crystallisation from EtOH, had m 104-105o. It was dissolved in Et2O and converted to the hydroxide by stirring with excess aqueous ammonia. The ether layer was separated, dried, and evaporated to give triphenyltin hydroxide which, after crystallisation from EtOH (or MeCN) and drying under vacuum, was in the form of white crystals (m 119-120o), which retained some cloudiness in the melt above 120o. The hydroxide retains water (0.1-0.5 moles of water per mole) tenaciously. [Glidewell & Liles Acta Cryst (B) 34 129 1978, Beilstein 16 H 914, 16 I 540, 16 II 625, 16 III 1240, 16 IV 1606.]

InChI:InChI=1/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1/rC18H15Sn.H2O/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H2/q+1;/p-1

Upstream product

• 53764-65-1 diphenyl-bromonium; iodide 
• 108-86-1 bromobenzene 
• 595-90-4 tetraphenyltin(IV) 
• 1064-10-4 hexaphenylditin 
• 7732-18-5 water 
• 88020-61-5 C₆H₅ISm 
• 114687-79-5 ethyleuropium iodide 
• 1135-99-5 diphenyltin(IV) dichloride 
• 33550-56-0 (iodomethyl)(triphenyl)stannane 
• 127916-72-7 triphenyl tin ⁽¹⁺⁾; 3,3-diethoxy-prop-1-yneide 
• 88068-44-4 methylytterbium 
• 19464-46-1 acetic acid-(2-triphenylstannyl-ethyl ester) 
• 1227-85-6 triphenylstannylacetylene 
• 23604-56-0 2-triphenylstannyl-ethanol 

Downstream Products

• 595-90-4 tetraphenyltin(IV) 
• 91-01-0 1,1-Diphenylmethanol 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 2847-64-5 triphenyl tin stearate 
• 1064-10-4 hexaphenylditin 
• 124908-58-3 dicyclohexylammonium S-triphenylstannylmercaptoacetate 
• 69706-08-7 diphenyltin-2-mercaptobenzoate 
• 124908-56-1 bis(triphenyltin) mercaptoacetate 
• 1247-08-1 Triphenyl-phenylethynyl-stannane 
• 114944-23-9 {bis(triphenylphosphine)nitrogen}{(triphenylstannyl)pentacarbonyltungsten} 
• 93671-50-2 triphenyltin cyanamide 
• 27533-17-1 bis(triphenylstannyl)carbodiimide 
• 127829-29-2 Sn{OCC(C(CH₃)3)CHC(C(CH₃)3)COCC(C(CH₃)3)CHC(C(CH₃)3)CHCNC}(C₆H₅)3 
• 108890-28-4 O-ethyl-O'-triphenylstannyl phosphonate 

Relevant academic research and scientific papers

Structural and in vitro biological studies of organotin(iv) precursors; Selective inhibitory activity against human breast cancer cells, positive to estrogen receptors

Crystals of Ph3SnCl (1) were grown from a methanol/acetonitrile solution. Compounds [Ph3SnOH]n (2) and [(Ph 2Sn)4Cl2O2(OH)2] (3) were crystallized from diethyl ether/methanol/acetonitrile and hot acetone/water solutions respectively, of the white precipitation, formed by adding KOH to solutions of 1 and [Ph2SnCl2] in 1:1 and 1:2 molar ratios respectively. Complex 1 was characterized by X-ray crystallography. X-ray structure determination of compounds 2 and 3 confirmed the previously reported identities. The molecular structure of 1, reported here, is a new polymorphic form of the known one for Ph3SnCl. Four independent [Ph 3SnCl] molecules constitute the crystal structure of 1. The moieties are packed in two pairs in a tail-to-tail arrangement. Complexes 1-3 were evaluated for their in vitro cytotoxic activity (cell viability) against human cancer cell lines: HeLa (human cervical), MCF-7 (breast, estrogen receptor (ER) positive), MDA-MB-231 (breast, ER negative), A549 (lung), Caki-1 (kidney carcinoma), 786-O (renal adenocarcinoma), K1 (thyroid carcinoma), and the normal human lung cell line MRC-5 (normal human fetal lung fibroblast cells) versus, the normal immortalized human mammary gland epithelial cell line MTSV17 with a sulforhodamine B (SRB) assay. The results show potent cytotoxic activity of the complexes against all cell lines used, which was superior to that of cisplatin (CDDP). Compounds 1-3 showed higher activity against breast cancer cells MCF-7 (ER positive) than against of MDA-MB-231 (ER negative). These findings prompted us to search for possible interaction of these complexes with other cellular elements of fundamental importance in cell proliferation. The influence of these complexes 1-3 upon the catalytic peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase (LOX), as well as their binding affinity towards calf thymus-DNA, were kinetically and theoretically studied.

catena-poly[[triphenyltin(IV)]-μ-hydroxo-κ2O:O] at 120 K

The structure of the title compound, [Sn(C6H5)3(OH)]n, has been re-investigated at 120 (2) K. The hydroxyl H atom was readily located and the threefold coordination about the O atom is planar. There are no hydro

Synthesis, structural characterization, Hirshfeld surface analysis and in vitro-antimicrobial activities of triphenyltin (IV) compounds of azo-carboxylates derived from 2- or 4-amino benzoic acids and naphthalen-1 or 2-ol

Synthesis of three new triphenyltin(IV) compounds 1–3 were reported by the reaction of azo-carboxylic acid ligands viz.2/4-(2-hydroxynaphthylazo)-benzoic acids [compounds 1 and 2] or 2-(4-hydroxynaphthylazo)-benzoic acid [compound 3] with triphenyltin(IV)

Antibacterial activity of diphenyltin(IV) and triphenyltin(IV) 3-chlorobenzoate againts Pseudomonas aeruginosa and Bacillus subtilis

In this paper, we reported the syntheses and antibacterial activity test of 2 organotin(IV) compounds, diphenyltin (IV) di-3-chlorobenzoate (2) and triphenyltin (IV) 3-chlorobenzoate (4). These two compounds were prepared by the reaction of diphenyltin (IV) dihydroxide and triphenyltin (IV) hydroxide with 3-chlorobenzoic acid. These compounds were characterized by 1H and 13C NMR, IR, UV-Vis spectroscopies and also based on the microanalytical data. The results of antibacterial activity by diffusion method against Pseudomonas aeruginosa and Bacillus subtilis showed that the triphenyltin(IV) 3-chlorobenzoate was active at concentration of 3.956 x 10-4M (200 ppm), while the chloramphenicol gave inhibition of 6.1894 x 10-4 M (200 ppm), although the halozone was bigger. This result indicated that compound 4 is potentially to be used as antibacterial substance, although the search of other derivative of organotin (IV) with other ligands is still needed to get much higher and much better activity.

The synthesis, characterization and comparative anticorrosion study of some organotin(IV) 4-chlorobenzoates

The synthesis of 3 compounds of a series of dibutyl(IV) di-4-chlorobenzoate, diphenyl(IV) di-4-chlorobenzoate and triphenyltin(IV) 4-chlorobenzoate have successfully been performed by reacting the dibutyltin(IV) dichloride, diphenyltin(IV) dichloride and triphenyltin(IV) chloride respectively via the dibutyltin(IV) oxide, diphenyltin(IV) dihydroxide and triphenyltin(IV) hydroxide with 4-chlorobenzoic acid. All compounds synthesized were well characterized by 1H and 13C NMR, IR and UV-Vis spectroscopies as well as based on the microanalytical data. The anticorrosion activity of these compounds were tested on Hot Roller Plate (HRP) mild steel in DMSO-HCl solution using potentiodynamic method. The results revealed that the triphenyltin(IV) 4-chlorobenzoate clearly showed the strongest inhibitor activity compared to the other derivatives, while diphenyltin(IV) compounds were better than that of dibutyltin(IV) analogous. The results reported here indicated that the optimal activity were depended on the ligand attached to the metal centre and might also be related to the number of carbon atoms present in the organotin(IV) used.

Synthesis and properties of Ph3Sn substituted tellurates - The crystal structures of trans-[(Ph3SnO)4Te(OH)2] and trans-[(Ph3SnO)2Te(OMe)4]

The reaction of Te(OH)6 with Ph3SnOH in ethanol leads to the formation of trans-[(Ph3SnO)4Te(OH)2] (1). Compound 1 crystallizes triclinic in the space group P1 with a = 996.6(2) pm, b = 1365.4(3) pm, c = 1368.2(3) pm and α = 71.15(2)°, β = 71.48(2)°, γ = 74.81(3)° (at 220 K). The molecular structure of 1 consists of a tellurium atom, which is coordinated nearly octahedrally by four Ph3SnO units and two hydroxyl groups that are trans to each other. The Te-O bond lengths are in the range of 190.5(2) and 193.7(2) pm. Treatment of 1 with methanol under reflux yields trans-[(Ph3SnO) 2Te(OMe)4] (2). Compound 2 crystallizes triclinic in the space group P1 with a = 1012.8(1) pm, b = 1422.4(2) pm, c = 1618.1(2) pm, and α = 100.44(1)°, β = 107.92(1)°, γ = 110.66(1)° (at 220 K). 2 forms centrosymmetric molecules in which the tellurium atom is surrounded nearly octahedrally by four methoxy groups and two trans arranged Ph3SnO units. The Te-O bond lengths of 187.9(3)-194.5(3) pm are similar to those observed in 1.

Thermal epimerization of diastereomeric Grignard reagents

Thermal epimerization is the key to changing the endo-to-exo ratio of the diastereomeric bornyl and fenchyl Grignard reagents from 67: 33 to 96: 4 and from 20: 80 to 80: 20, respectively.

MULTICOMPARTMENT GRANULATE FORMULATIONS FOR ACTIVE SUBSTANCES

The invention relates to molded article that contains active substances and comprises at least two compartments that have a different material composition. Each compartment is independently provided with at least one active substance that is contained in a matrix. Each matrix encompasses at least one filler at a concentration of ≧20 percent by weight to ≦100 percent by weight relative to the total weight of the respective matrix. The invention further relates to a method for producing such molded articles as well as the use thereof.

Hydrolysis of dimethylphenyltin(IV) and triphenyltin(IV) chlorides in different aqueous ethanol solutions

The hydrolysis of [(Me)2(Ph)Sn(IV)]+ and [(Ph) 3Sn(IV)]+ has been investigated at 25 °C and different aqueous solutions of ethanol, using a combination of spectrophotometric and potentiometric techniques. The species formed together with their formation constants have been determined using the computer program Squad over a wide pH range of 1 to 11. The hydrolysis constants in different media were analyzed in terms of Kamlet and Taft parameters. Single-parameter correlation of the formation constants, K11 and K12, versus α (hydrogen-bond donor acidity), β (hydrogenbond acceptor basicity), and π* (dipolarity/polarizability) for both cases are relatively poor in all solutions, but multiparameter correlation represents significant improvement with regard to the single-parameter models. In this work, we have also used the normalized polarity parameter, ETN, alone and in combination with the Kamlet-Taft parameter to find a better correlation of the formation constants in different aqueous ethanol solutions.

Structural investigations on diorgano- and triorganotin(IV) derivatives of [meso-tetra(4-sulfonatophenyl)porphine] metal chlorides

Several new complexes of organotin(IV) moieties with MCl n[meso-tetra(4-sulfonatophenyl)porphine], (R2Sn) 2MCln[meso-tetra(4-sulfonatophenyl)-porphinate]s and (R3Sn)4MCln [meso-tetra(4-sulfonatophenyl) porphinate]s, [M = Fe(III), Mn(III): n = 1, R = Me, n-Bu; Ph; M = Sn(IV): n = 2, R = Me, n-Bu] have been synthesized and their solid state configuration investigated by infrared (IR) and M?ssbauer spectroscopy, and by 1H and 13C NMR in D2O. The electron density on the metal ion coordinated inside the porphyrin ring is not influenced by the organotin(IV) moieties bonded to the oxygen atoms of the side chain sulfonatophenyl groups, as it has been inferred on the basis of M?ssbauer spectroscopy and, in particular, from the invariance of the isomer shift of the Fe(III) and Sn(IV) atoms coordinated into the porphyrin square plane of the newly synthesized complexes, with respect to the same atoms in the free ligand. As far as the coordination polyhedra around the peripheral tin atoms are concerned, infrared spectra and experimental M?ssbauer data would suggest octahedral and trigonal bipyramidal environments around tin, in polymeric configurations obtained, respectively, in the diorganotin derivatives through chelating or bridging sulfonate groups coordinating in the square plane, and in triorganotin(IV) complexes through bridging sulfonate oxygen atoms in axial positions. The structures of the (Me3Sn)4Sn(IV)Cl 2[meso-tetra(4-sulfonatophenyl)porphinate] and of the two model systems, Me3Sn(PS)(HPS) and Me2Sn(PS)2 [HPS = phenylsulfonic acid], have been studied by a two layer ONIOM method, using the hybrid DFT B3LYP functional for the higher layer, including the significant tin environment. This approach allowed us to support the structural hypotheses inferred by the IR and M?ssbauer spectroscopy analysis and to obtain detailed geometrical information of the tin environment in the compounds investigated. 1H and 13C NMR data suggested retention of the geometry around the tin(IV) atom in D2O solution.