60835-69-0

Usage

Uses

Used in Chemical Synthesis:
4-Nitrobenzo-15-crown-5 is used as a raw material and intermediate in chemical synthesis processes. Its unique ability to form complexes with cations allows it to facilitate various chemical reactions and improve the overall efficiency of the synthesis.
Used in Pharmaceutical Industry:
4-Nitrobenzo-15-crown-5 is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and the improvement of existing ones. Its cation-complexing properties can enhance the solubility, stability, and bioavailability of active pharmaceutical ingredients.
Used in Separation of Cations:
4-Nitrobenzo-15-crown-5 is used as a selective agent to separate cations in various applications, such as analytical chemistry, environmental monitoring, and industrial processes. Its ability to form stable complexes with specific cations allows for efficient and selective separation techniques.
Used in Dissolution of Inorganic Salts:
4-Nitrobenzo-15-crown-5 is used to dissolve inorganic salts into organic solvents, enabling the performance of naked anion chemistry. This property is particularly useful in the synthesis of new compounds and the study of anion-specific reactions.
Used as Phase Transfer Catalysts:
4-Nitrobenzo-15-crown-5 serves as a phase transfer catalyst, facilitating the transfer of cations between immiscible aqueous and organic phases. This function is essential in various chemical reactions, particularly those involving the synthesis of complex organic molecules.
Used in Chiral Crown Ethers:
Chiral forms of 4-Nitrobenzo-15-crown-5 have been used to resolve racemic mixtures or separate isomers by chiral chromatography. This application is crucial in the pharmaceutical industry, where the separation of enantiomers is often necessary to obtain the desired biological activity and avoid potential side effects.

Purification Methods

Recrystallise the crown ether from EtOH, MeOH or *C6H6/hexane as for the 18-crown-6 compound below. It complexes with Na+, K+, NH4+, Ca2+, Mg2+ and Cd2+. The 1HNMR spectrum (CDCl3) has (ppm): 3.6-4.4 (m 16CH2), 6.8 (d 1H arom), 7.65 (d 1H arom), 7.80 (dd 1H arom Jab 9Hz and Jbc 3Hz) [Schmid et al. J Am Chem Soc 98 5198 1976, Kikukawa et al. Bull Chem Soc Jpn 50 2207 1977, Toke et al. Justus Liebigs Ann Chem 349 349, 761 1988, Lindner et al. Z Anal Chem 322 157 1985].

InChI:InChI=1/C14H19NO7/c16-15(17)12-1-2-13-14(11-12)22-10-8-20-6-4-18-3-5-19-7-9-21-13/h1-2,11H,3-10H2

Upstream product

• 100460-06-8 2-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-4-nitro-phenol 
• 14098-44-3 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin 
• 120-80-9 benzene-1,2-diol 
• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 

Downstream Products

• 99624-13-2 4',5'-dinitrophenyl crown ether 15C₅ 
• 1562207-49-1 C₂₃H₂₇NO₈ 
• 1262682-18-7 C₂₁H₂₆N₂O₆ 
• 1262682-15-4 C₂₂H₂₉IN₂O₆ 
• 1262682-14-3 C₁₇H₂₇IN₂O₆ 
• 1262682-11-0 C₂₁H₂₇IN₂O₆ 
• 1262682-10-9 C₁₇H₂₇IN₂O₆ 
• 1262682-07-4 C₁₆H₂₅IN₂O₆ 
• 1262682-05-2 C₂₂H₂₉ClN₂O₆ 
• 1262682-03-0 C₁₇H₂₇ClN₂O₆ 
• 1262682-02-9 C₂₁H₂₇ClN₂O₆ 

Relevant academic research and scientific papers

Preparation, photophysical, electrochemical, and ion-binding properties of Ru(II) polypyridyl complexes containing a crown ether unit

Two polypyridyl ligands, 4'-(4,5-diazafluoren-9-ylimino)benzo-15-crown-5 (L1) and 4'-(4,5-diazafluoren-9-ylimino)benzo-12-crown-4 (L 2), and their Ru(II) complexes [(bpy)2RuL](PF 6)2 and [(bpy)2RuL2](PF 6)2, respectively, have been synthesized and characterized. The two complexes display metal-to-ligand charge transfer absorptions at around 444 nm in CH3CN solution at r. t. and emission at around 573 nm in an EtOH-MeOH (4:1, v/v) glassy matrix at 77 K. Electrochemical studies of the complexes show one Ru(II)-centered oxidation at around 1.33 V and three ligandcentered reductions. The binding ability of the complexes with Na+ and Li+ has been investigated by UV/Vis absorption and emission spectroscopy and electrochemical titrations. Addition of Na+ and Li+ to solutions of the complexes results in a progressive quenching of the emission, a hyperchromic effect of the UV/Vis absorption, and a progressive cathodal shift of the Ru(II)-centered E 1/2 potential. The stability constants for the stoichiometric 1:1 ratio of the complexes and the cations have been obtained by UV/Vis absorption titration.

ESI-MS Detection of Very Weak π-Stacking Interactions in the Mixed-Ligand Sandwich Complexes Formed by Substituted Benzo-Crown Ethers and Metal Cations

The stability of the mixed-ligand complex formed by amino-benzo-15-crown-5 and nitro-benzo-15-crown-5, with a metal cation, [NH2B15C5 + NO2B15C5 + K]+, was found to be enhanced by π-stacking interactions. This conclusion was deduced by comparison of the abundance of the mixed-ligand complex with the abundances of homo-ligand complexes ([(NH2B15C5)2 + K]+, [(NO2B15C5)2 + K]+), as well as with those of 1:1 complexes ([NH2B15C5 + K]+, [NO2B15C5 + K]+). Some solvents and some metal cations with large radii were also found to prevent the existence of π-stacking interactions.

Chalcogen Bond Mediated Enhancement of Cooperative Ion-Pair Recognition

A series of heteroditopic receptors containing halogen bond (XB) and unprecedented chalcogen bond (ChB) donors integrated into a 3,5-bis-triazole pyridine structure covalently linked to benzo-15-crown-5 ether motifs exhibit remarkable cooperative recognition of halide anions. Multi-nuclear 1H, 13C, 125Te and 19F NMR, ion pair binding investigations reveal sodium cation–benzo-crown ether binding dramatically enhances the recognition of bromide and iodide halide anions, with the chalcogen bonding heteroditopic receptor notably displaying the largest enhancement of halide binding strength of over two hundred-fold, in comparison to the halogen bonding and hydrogen bonding heteroditopic receptor analogues. DFT calculations suggest crown ether sodium cation complexation induces a polarisation of the sigma hole of ChB and XB heteroditopic receptor donors as a significant contribution to the origin of the unique cooperativity exhibited by these systems.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.

Production of macrocyclic polyether benzo-15-crown-5 and its functional derivatives

Study of interaction between catechol and tetraethylene glycol dichloride in the n-butanol media, resulting with benzo-15-crown-5 production. Production of nitro- and amino-derivatives of benzo-15-crown-5. Determination of their thermogravimetric characteristics.

Synthesis and properties of macroheterocyclic azomethines based on 4-aminobenzo-15-crown-5

A number of new stable azomethine crown ether derivatives have been synthesized by condensation of 4-aminobenzo-15-crown-5 with aromatic aldehydes. Complexation of the products with transition metal cations (Cu2+, Zn2+, Fe3+, Co3+, Ni3+) has been studied by spectrophotometry.

Supramolecular assembly of isocyanorhodium(i) complexes: An interplay of rhodium(i)···rhodium(i) interactions, hydrophobic-hydrophobic interactions, and host-guest chemistry

A series of tetrakis(isocyano)rhodium(I) complexes with different chain lengths of alkyl substituents has been found to exhibit a strong tendency toward solution state aggregation upon altering the concentration, temperature and solvent composition. Temperature- and solvent-dependent UV-vis absorption studies have been performed, and the data have been analyzed using the aggregation model to elucidate the growth mechanism. The aggregation is found to involve extensive Rh(I)···Rh(I) interactions that are synergistically assisted by hydrophobic-hydrophobic interactions to give a rainbow array of solution aggregate colors. It is noted that the presence of three long alkyl substituents is crucial for the observed cooperativity in the aggregation. Molecular assemblies in the form of nanoplates and nanovesicles have been observed in the hexane-dichloromethane solvent mixtures, arising from the different formation mechanisms based on the alkyl chain length of the complexes. Benzo-15-crown-5 moieties have been incorporated for selective potassium ion binding to induce dimer formation and drastic color changes, rendering the system as potential colorimetric and luminescent cation sensors and as building blocks for ion-controlled supramolecular assembly.

Novel benzo-15-crown-5/C60 dyads with different chains: Synthesis and complexation properties

Using benzo-15-crown-5 derivatives as starting materials, two novel benzo-15-crown-5/C60 dyads with different linking chains were designed and synthesized in good yields by 1,3-dipolar cycloaddition of azomethine ylide generated in situ from al

Self-assembled dimerization of bis(crown ether)-2,2′-bibenzimidazoles

Bis(crown ether)-2,2′-bibenzimidazole 1 and its 1-substituted derivatives were synthesized as new self-assembled motifs. UV-vis and 1HNMR titration experiments of 1 with potassium ions in a mixture of chloroform and methanol (1:1) were carried out. The stoichiometries and curve fitting analysis showed that a 2:2 complex of 1 with potassium ions was formed in a face-to-face fashion. 1-Monosubstituted bis(crown ether)-2,2′- bibenzimidazole 6a having a (dodecylaminocarbonyl)methyl group also gave a 2:2 complex with potassium ions. Structural analysis of the 2:2 complex of 6a with potassium ions was performed using various two-dimensional NMR techniques. Results suggested that, of eight or more possible conformational isomers, the one having the two substituent groups diagonally opposite each other was predominantly formed. Reversible association and dissociation of the 2:2 complex was observed after adding potassium ions and then removing them with an 18-crown-6-ether.

Nitro derivatives of N-alkylbenzoaza-15-crown-5: Synthesis, structures, and complexation with metal and ammonium cations

A number of N-alkylnitrobenzoaza-15-crown-5 with the macrocycle N atom conjugated with the benzene ring were obtained. The structural and complexing properties of these compounds were compared with those of model nitrobenzo- and N-(4-nitrophenyl)aza-15-cr