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Usage

Uses

Used in Organic Synthesis:
[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl](triphenyl)phosphonium is used as a reactant in organic synthesis, particularly for the formation of carbon-phosphorus bonds. Its unique reactivity makes it a valuable tool in creating new chemical structures and compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, [(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl](triphenyl)phosphonium is used as a precursor for the development of new drugs. Its potential biological activities, including anti-tumor and anti-fungal properties, make it a promising candidate for the creation of therapeutic agents.
Used in Material Science:
[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl](triphenyl)phosphonium's unique structure also makes it useful in material science, where it can be employed as a component in the synthesis of advanced materials with specific properties, such as those required for electronics or energy storage applications.
Used in Research and Development:
Due to its potential applications in various fields, [(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl](triphenyl)phosphonium is also used in research and development settings to explore new methods of synthesis, investigate its biological activities further, and identify additional potential uses.

Upstream product

• 5332-26-3 N-(bromomethyl)phtalimide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 115808-81-6 2-[(Z)-2-(4-Chloro-phenyl)-vinyl]-isoindole-1,3-dione 

Relevant academic research and scientific papers

Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl] isothioureas: High affinity and human/rat species-selective histamine H 3 receptor antagonists

S-Alkyl-N-alkylisothiourea compounds containing various cyclic amines were synthesized in the search for novel nonimidazole histamine H3 receptor (H3R) antagonists. Among them, four N-alkyl S-[3-(piperidin-1-yl)propyl]isothioureas 18, 19, 22, and 23 were found to exhibit potent and selective H3R antagonistic activities against in vitro human H3R, but were inactive against in vitro human H 4R. Furthermore, three alkyl homologs 18-20 showed inactivity for histamine release in in vivo rat brain microdialysis, suggesting differences in antagonist affinities between species. In addition, in silico docking studies of N-[4-(4-chlorophenyl)butyl]-S-[3-piperidin-1-yl)propyl]isothiourea 19 and a shorter homolog 17 with human/rat H3Rs revealed that structural differences between the antagonist-docking cavities of rat and human H 3Rs were likely caused by the Ala122/Val122 mutation.

Aminomethyl and aminoacetyl complexes of palladium(II), platinum(II), iron(II) and rhenium(I) with N-phthaloyl as amino protecting group and mechanistic studies on the palladium-catalyzed amidocarbonylation

New aminomethyl and aminoacetyl complexes with N-phthaloyl as the amino protecting group were synthesised by oxidative addition of N-phthaloylmethyl or -acetyl halide to carbonylmetallates or to Pd(PPh3)4 or [Pt(C2H4)(PPh3)2] to give [Re{C(O)CH2N-phthaloyl}(CO)5] (1), [FeCp(CH 2N-phthaloyl)(CO)2] (2), [FeCp{C(O)CH2N- phthaloyl}(CO)2] (3), trans-[PdBr(CH2N-phthaloyl)(PPh 3)2] (4) and trans-[Pd{C(O)CH2N-phthaloyl}(X) (PPh3)2] (X = Br, Cl; 5, 6). The bis(phosphane) complexes [Pd(CH2N-phthaloyl)(X)-(R2PCH2CH 2PR2)] and [Pd{C(O)CH2N-phthaloyl}(X)-(R 2PCH2CH2PR2)] (X = Cl, Br; R = Ph, C6H11) 8-13 were obtained by ligand exchange from 4, 5 or 6 with the corresponding bis(phosphanes). Halide abstraction from 4, 5, 6, 10, 11 or 12 gives the cationic complexes 14 and 15 with formation of a five-membered chelate ring which includes one carbonyl atom of the phthaloyl group. The reaction of 6 with the tridentate ligand PhP(CH2CH 2PPh2)2 affords the five-coordinate complex 16 and from [Pt(C2H4)(PPh3)2] and organic halides the platinum(II) complexes trans-[Pt(CH2N-phthaloyl) (Cl)(PPh3)2] (17) and [PtC(O)CH(CH2Ph)N- phthaloyl(Cl)(PPh3)2] (18) were isolated. The structures of 2, 11, 14, 15 and 16 were determined by single-crystal X-ray analysis. The mechanism of the palladium-catalysed amidocarbonylation was studied using phthalimide, formaldehyde and CO as a model system which gives N-phthaloylglycine in good yield. The proposed elementary steps in the palladium-catalysed amidocarbonylation could be verified by use of the possible intermediates phthaloyl-NCH2OH and phthaloyl-NCH2Br as substrates, by oxidative addition of phthaloylmethyl bromide to Pd0, by insertion of CO into the palladium-carbon-bond of 4 and 8 with formation of 5 or 9, respectively, and by use of the isolated possible intermediates 4, 5 and 14 as catalysts. Thus, all crucial steps of the palladium-catalysed amidocarbonylation with the model system phthalimide/formaldehyde/CO have been verified for the first time. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis and antitumor properties of some isoindolylalkylphosphonium salts

Antitumor evaluation of 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyltriphenylphosphonium bromide (1) revealed significant activity in P-388 lymphocytic leukemia (T/C = 160%). As a follow-up to this chemical lead, a series of closely related phosphonium salts was prepared in which the 1,3-dihydro-1,3-dioxo-2H-isoindole ring system was maintained or in which it was replaced by other moieties such as maleimido, bromo, methoxy, and isoindoline. Syntheses generally involved treatment of the appropriate N-(bromoalkyl)phthalimide with the required phosphine or condensation of the K salt of the substituted imide with β-(bromoethyl) triphenylphosphonium bromide. From the biological data obtained for these compounds, several requirements can be defined for substantial antileukemic activity. Of utmost importance is the presence of a triarylphosphonium halide moiety, coupled to an alkyl chain of two or three carbon atoms. The preferred terminus of the alkyl chain is the 1,3-dihydro-1,3-dioxo-2H-isoindole ring system, although the observed activity of β-(bromoethyl)triphenylphosphonium bromide (T/C = 127%) would suggest that a superior carrier molecule could be developed.