60835-69-0

Basic information

• Product Name: 4-NITROBENZO-15-CROWN-5
• Synonyms: 2,3,5,6,8,9,11,12-Octahydro-15-nitro-1,4,7,10,13-benzopentaoxacyclopentadecin;CROWN ETHER/4'-NITROBENZO-15-CROWN-5 FOR;Crown ether/4'-Nitrobenzo-15-crown-5 for synthesis;15-Nitro-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine;17-Nitro-2,3-benzo-1,4,7,10,13-pentaoxacyclopentadecen-2;NITROBENZO-15-CROWN-5;CROWN ETHER/4'-NITROBENZO-15-CROWN-5;2,3-(4-NITROBENZO)-1,4,7,10,13-PENTAOXACYCLOPENTADEC-2-ENE
• CAS NO: 60835-69-0
• Molecular Formula: C₁₄H₁₉NO₇
• Molecular Weight: 313.3
• Product Categories: Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;Chelation/Complexation Compounds;Crown Ethers;Synthetic Reagents
• Mol File: 60835-69-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 93-97 °C(lit.)
• Boiling Point: 453.11°C (rough estimate)
• Flash Point: 199 °C
• Appearance: light yellow granular powder
• Density: 1.191
• Vapor Pressure: 1.74E-08mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: It is soluble in non-polar solvents.
• BRN: 1598970
• CAS DataBase Reference: 4-NITROBENZO-15-CROWN-5(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROBENZO-15-CROWN-5(60835-69-0)
• EPA Substance Registry System: 4-NITROBENZO-15-CROWN-5(60835-69-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 60835-69-0(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW GRANULAR POWDER

Uses

4-Nitrobenzo-15-crown-5 is a raw material used in synthesis as well as an intemediate in chemical syntheis and pharmaceutica intemediate. It is also used to separate cations, dissolve inorganic salts into organic solvents to perform naked anion chemistry, serve as phase transfer catalysts, and chiral crown ethers have been used to resolve racemic mixtures or separate isomers by chiral chromatography.

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

• 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 
• 100460-06-8 2-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-4-nitro-phenol 

Downstream Products

• 194923-90-5 2-(2-{2-[2-(2-Methylamino-5-nitro-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol 
• 99624-13-2 4',5'-dinitrophenyl crown ether 15C₅ 
• 1262682-18-7 C₂₁H₂₆N₂O₆ 
• 1262682-15-4 C₂₂H₂₉IN₂O₆ 
• 1262682-14-3 C₁₇H₂₇IN₂O₆ 
• 1262682-11-0 C₂₁H₂₇IN₂O₆ 
• 1262682-10-9 C₁₇H₂₇IN₂O₆ 

Relevant articles and documents

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.

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.

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.

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.