73805-86-4

Usage

Uses

Used in Organic Chemical Synthesis:
(4-nitrobenzyl)(triphenyl)phosphonium iodide serves as a powerful and selective electron transfer reagent in various synthetic transformations, facilitating complex chemical reactions that would otherwise be challenging to achieve.
Used as a Catalyst in Cross-Coupling Reactions:
In the field of organic chemistry, (4-nitrobenzyl)(triphenyl)phosphonium iodide is utilized as a catalyst to expedite cross-coupling reactions and other organic transformations, enhancing the efficiency and selectivity of these processes.
Used in Organic Reactions as a Reagent:
(4-nitrobenzyl)(triphenyl)phosphonium iodide is also employed as a reagent in a wide array of organic reactions, contributing to the advancement of chemical research and the development of new compounds with potential applications across various industries.

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 555-16-8 4-nitrobenzaldehdye 
• 3145-86-6 4-nitrobenzyl iodide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1302579-22-1 (S)-2,2-dimethyl-4-[(E)-2-(4-nitrophenyl)vinyl]oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Ionic Liquids as Solvents for SN2 Processes. Demonstration of the Complex Interplay of Interactions Resulting in the Observed Solvent Effects

Bimolecular nucleophilic substitution reactions between triphenylphosphine and benzylic electrophiles have been examined in an ionic liquid to probe interactions with species along the reaction coordinate. Trends in the rate constant were found on both varying the leaving group and the electronic nature of the aromatic ring. In all the cases considered, interactions between the components of the ionic liquid and the transition state were shown to be more significant in determining reaction outcome than previously observed for this class of reaction. This demonstrates the importance of considering interactions of the ionic liquid components with all species along the reaction coordinate when investigating the origin of ionic liquid solvent effects, along with how such effects might be exploited.

Synthesis of a novel series of 2,3,4-trisubstituted oxazolidines designed by isosteric replacement or rigidification of the structure and cytotoxic evaluation

We have previously reported on a study of the structure-activity relationship in a series of 2,3,4-substituted oxazolidines recently discovered by our group varying the substituent at the ring or stereochemistry of the oxazolidine ring. We discovered the cytotoxic and pro-apoptotic potential of compounds 1 and 2 with good selectivity against cancer cell lines. In the present study we describe the synthesis and cytotoxic evaluation against cancer cell lines (HL60, JURKAT, MDA-MB-231 and LNCaP) of a series of oxazolidines designed by isosteric replacement or rigidification of the oxymethylene spacer of compounds 1 and 2. Alkenes 3 and 4 retained the activity against MDA-MB-231 cells and they were more active on HL60, JURKAT and LNCaP cells. Considering LNCaP cells, E-isomer 4 was at least 7 times and about 3 times more potent than lead 1 and Z-isomer 3, respectively. Compound 4 exerted significant activity against LNCaP with IC50 in the low micromolar range (11 μM) without affecting VERO cells and PBMC proliferation (IC50 > 100 μM) indicating its low toxicity to normal cells.