1530-41-2

Basic information

• Product Name: (3-nitrobenzyl)(triphenyl)phosphonium
• CAS NO: 1530-41-2
• Molecular Formula: Br*C₂₅H₂₁NO₂P
• Molecular Weight: 398.413
• Mol File: 1530-41-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (3-nitrobenzyl)(triphenyl)phosphonium(CAS DataBase Reference)
• NIST Chemistry Reference: (3-nitrobenzyl)(triphenyl)phosphonium(1530-41-2)
• EPA Substance Registry System: (3-nitrobenzyl)(triphenyl)phosphonium(1530-41-2)

Safety Data

• Hazardous Substances Data: 1530-41-2(Hazardous Substances Data)

Usage

Description

(3-nitrobenzyl)(triphenyl)phosphonium is a phosphonium salt with the molecular formula C25H20N2O2P. It features a 3-nitrobenzyl group and three triphenylphosphonium groups, making it a versatile and important compound in organic chemistry.

Uses

Used in Organic Synthesis:
(3-nitrobenzyl)(triphenyl)phosphonium is used as a reactant for the formation of carbon-carbon bonds and as a precursor in the production of pharmaceuticals and agrochemicals. Its presence in organic synthesis aids in creating complex molecular structures.
Used as a Phase-Transfer Catalyst:
In the chemical industry, (3-nitrobenzyl)(triphenyl)phosphonium is utilized as a phase-transfer catalyst to facilitate organic reactions, particularly those involving the transfer of reactants between phases with different polarities.
Used in the Synthesis of Heterocyclic Compounds:
(3-nitrobenzyl)(triphenyl)phosphonium is employed as a reagent in the synthesis of heterocyclic compounds, which are important in various fields such as pharmaceuticals, agrochemicals, and materials science.
Used for Nitration and Reduction Reactions:
The nitro group in (3-nitrobenzyl)(triphenyl)phosphonium makes it useful for nitration reactions, where the nitro group is introduced into an organic molecule. Additionally, it can be used in reduction reactions, where the nitro group is reduced to other nitrogen-containing functional groups.
Used to Enhance Solubility and Reactivity:
The phosphonium moiety in (3-nitrobenzyl)(triphenyl)phosphonium improves its solubility in organic solvents, which is crucial for many organic reactions. This enhanced solubility also contributes to its reactivity, making it a preferred choice in various chemical processes.

Upstream product

• 99-08-1 1-methyl-3-nitrobenzene 
• 603-35-0 triphenylphosphine 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 

Downstream Products

• 15866-63-4 1-(m-Nitrophenyl)-4-phenyl-1,3-butadien 
• 89302-80-7 (m-Nitrophenyl)allene 
• 98460-10-7 11-Fluoro-9-[(E)-2-(3-nitro-phenyl)-vinyl]-dibenzo[c,g]phenanthrene 
• 61110-97-2 (3-nitrobenzylidene)triphenylphosphorane 
• 14064-52-9 3-nitrostilbene 
• 622861-41-0 5-methoxy-2-[(E)-2-(3-nitrophenyl)ethenyl]-1H-indole 
• 936103-90-1 C₂₁H₂₇NO₄Si 
• 936103-92-3 C₂₁H₂₇NO₄Si 
• 622861-42-1 9-methoxy-4-(3-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 

Relevant articles and documents

Photochemical and Thermal Hydrations of Aromatic Allenes. Evidence for Allyl and Vinyl Cation Intermediates

The photohydration of aromatic allenes has been studied in water and in dilute aqueous sulfuric acid (0-25percent H2SO4).It was found that phenylallene (2a) and α-methylphenylallene (2b) undergo photohydration to give the corresponding cinnamyl alcohol derivatives.The proposed mechanism involves protonation of the central carbon of phenylallenes in their singlet excited state (S1).In contrast, (p-nitrophenyl)allene (2g) and (m-nitrophenyl)allene (2h) gave the corresponding (nitrophenyl)acetones.The mechanism for the formation of these ketones is believed to be due to initial protonation of the α- or γ-carbon atom of the (nitrophenyl)allene in the triplet excited state (T1).Phenylallenes with CN, CF3, and F substituents failed to photohydrate.The results of these photohydrations were compared with those of the much slower thermal hydrations in 70-83percent H2SO4.Phenylallenes 2a and 2b cyclized to the corresponding indene derivatives in 70percent H2SO4.Phenylallenes with NO2-substituents (2g-2h) underwent hydration to give the corresponding (nitrophenyl)acetones (expected products) and (nitrophenyl)-1-propanones (unexpected products) in 83percent H2SO4.Similar results were obtained with (m-cyanophenyl)allene.The formation of both types of ketone is discussed in terms of the intermediacy of a common vinyl cation intermediate.

Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands

Site-selective nitrene transfer to di- and polyene substrates has been achieved using designed peptide-embedded bioxazoline ligands capable of binding copper. In model 1,3-diene substrates, the olefinic position proximal to a directing group was selectively functionalized. Additional studies indicate that this selectivity stems from non-covalent substrate-catalyst interactions. The peptide-mediated nitrene transfer was also applied to polyene natural product retinol and selective proximal functionalization allowed access to a cis-pyrroline modified retinoid. (Figure presented.).

Potent and selective double-headed thiophene-2-carboximidamide inhibitors of neuronal nitric oxide synthase for the treatment of melanoma

Selective inhibitors of neuronal nitric oxide synthase (nNOS) are regarded as valuable and powerful agents with therapeutic potential for the treatment of chronic neurodegenerative pathologies and human melanoma. Here, we describe a novel hybrid strategy