5350-96-9

Usage

Uses

Used in Organic Synthesis:
(4-NITROBENZYL)TRIMETHYLAMMONIUM CHLORIDE is used as a phase-transfer catalyst for facilitating reactions between organic and inorganic compounds. Its ability to transfer reactants between different phases allows for more efficient and selective reactions, making it a valuable tool in organic synthesis.
Used in Pharmaceutical Industry:
(4-NITROBENZYL)TRIMETHYLAMMONIUM CHLORIDE is used as an intermediate in the synthesis of certain pharmaceuticals. Its unique chemical structure allows it to be incorporated into drug molecules, potentially enhancing their efficacy or modifying their properties.
Used in Specialty Chemicals:
(4-NITROBENZYL)TRIMETHYLAMMONIUM CHLORIDE is used in the preparation of specialty chemicals, such as dyes, pigments, and other compounds with specific properties. Its versatility and reactivity make it a useful building block in the development of these specialized products.
Used in Research:
(4-NITROBENZYL)TRIMETHYLAMMONIUM CHLORIDE is used as a research compound to study its properties and potential applications. Its unique structure and reactivity make it an interesting subject for scientific investigation, potentially leading to new discoveries and applications in various fields.

InChI:InChI=1/C10H15N2O2.ClH/c1-12(2,3)8-9-4-6-10(7-5-9)11(13)14;/h4-7H,8H2,1-3H3;1H/q+1;/p-1

Upstream product

• 19824-21-6 C₁₀H₁₅N₂O₂⁽¹⁺⁾*Br^(1-) 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 
• 75-50-3 trimethylamine 

Downstream Products

• 4336-57-6 trans-2-(4-nitrophenyl)-3-phenyloxirane 

Relevant academic research and scientific papers

Shape-Selective Recognition of Quaternary Ammonium Chloride Ion Pairs

Synthetic receptors that recognize ion pairs are potentially useful for many technical applications, but to date there has been little work on selective recognition of quaternary ammonium (Q+) ion pairs. This study measured the affinity of a tetralactam macrocycle for 11 different Q+·Cl- salts in chloroform solution. In each case, NMR spectroscopy was used to determine the association constant (Ka) and the structure of the associated complex. Ka was found to depend strongly on the molecular shape of Q+ and was enhanced when Q+ could penetrate the macrocycle cavity and engage in attractive noncovalent interactions with the macrocycle's NH residues and aromatic sidewalls. The highest measured Ka of 7.9 × 103 M-1 was obtained when Q+ was a p-CN-substituted benzylic trimethylammonium. This high-affinity Q+·Cl- ion pair was used as a template to enhance the synthetic yield of macrocyclization reactions that produce the tetralactam receptor or structurally related derivatives. In addition, a permanently interlocked rotaxane was prepared by capping the end of a noncovalent complex composed of the tetralactam macrocycle threaded by a reactive benzylic cation. The synthetic method provides access to a new family of rotaxanated ion pairs that can likely act as anion sensors, molecular shuttles, or transport molecules.

Benzylic Ammonium Ylide Mediated Epoxidations

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

Alkyl Transfer from Quaternary Ammonium Salts to Cobalt (I): Model for the Cobalamin-Dependent Methionine Synthase Reaction

The reaction of cobaloxime(I) with diverse quaternary ammonium salts leads, in general, to a group transfer from nitrogen to cobalt.The behaviour of the salts in these transalkylations is consistent with an SN2 mechanism, involving Co(I) as a n