54533-83-4

Basic information

• Product Name: BENZOAZA-15-CROWN-5, 99
• Synonyms: BENZOAZA-15-CROWN-5, 99
• CAS NO: 54533-83-4
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.323
• Mol File: 54533-83-4.mol

Chemical Properties

• Melting Point: 147-149°C
• Boiling Point: 410.51°C (rough estimate)
• Flash Point: 167.9°C
• Appearance: /
• Density: 1.1116 (rough estimate)
• Vapor Pressure: 7.56E-07mmHg at 25°C
• Refractive Index: 1.5280 (estimate)
• CAS DataBase Reference: BENZOAZA-15-CROWN-5, 99(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOAZA-15-CROWN-5, 99(54533-83-4)
• EPA Substance Registry System: BENZOAZA-15-CROWN-5, 99(54533-83-4)

Safety Data

• Hazardous Substances Data: 54533-83-4(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE CRYSTALLINE POWDER

InChI:InChI=1/C14H21NO4/c1-2-4-14-13(3-1)18-11-9-16-7-5-15-6-8-17-10-12-19-14/h1-4,15H,5-12H2/p+1

Upstream product

• 54535-06-7 bis(o-phenylene)glycol ditosylate 
• 10234-40-9 2,2'-(1,2-phenylenedioxy)diethanol 
• 41024-87-7 1,2-bis(5-hydroxy-3-oxa-1-pentyloxy)benzene ditosylate 
• 107102-14-7 2,3-benzo-10-benzyl-10-aza-1,4,7,13-tetraoxa-2-cyclopentadecene 
• 111-42-2 2,2'-iminobis[ethanol] 
• 54533-82-3 2,3-benzo-10-tosyl-10-aza-1,4,7,13-tetraoxa-2-cyclopentadecene 

Downstream Products

• 186602-75-5 C₂₅H₃₅NO₅ 
• 145594-20-3 N-(Boc-Tyr(Boc)-D-Ala-Gly-Phe-Leu-Ahx)-benzoaza-15-crown-5 
• 145611-62-7 N-(N'-tert-butoxycarbonylleucyl-6-aminohexanoyl)benzoaza-15-crown-5 
• 700375-37-7 11-(2-heptyloxy-5-nitro-benzyl)-6,7,10,11,12,13,15,16-octahydro-9H-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecene 
• 700375-38-8 11-(2-benzyloxy-5-nitro-benzyl)-6,7,10,11,12,13,15,16-octahydro-9H-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecene 
• 918548-86-4 N-(2-hydroxy-3-formyl-5-chlorobenzyl)-10-aza-benzo-15-crown-5 

Relevant articles and documents

Synthesis of monoazacrown ethers under phase-transfer catalysis

A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect. Pleiades Publishing, Ltd., 2012.

Substitution effect, absorption, and fluorescence behaviors of 11,12-benzo-1,7,10,13-tetraoxa-4-azacyclopentadec-11-ene (Benzoaza-15-crown-5) derivatives upon cation complexation in solvent extraction

Substitution effect, absorption, and fluorescence behaviors of some benzoaza-15-crown-5 derivatives upon cation complexation in solvent extraction were studied. The introduction of a substituent on the nitrogen atom in benzoaza-15-crown-5 enhanced extractabilities in the solvent extraction of aqueous alkali metal picrates. The nondonating substituents raised the cation selectivity for Na+ over K+, but the donating substituents reduced the cation selectivity. The absorption and fluorescence spectral behavior was different with the alkali metal cations.

Synthesis, structural characterization and complexation properties of the first "crowned" dipyrrolylquinoxalines

The synthesis of four crown-substituted dipyrrolylquinoxalines 1-4 is reported. The key step in the synthesis is reaction of a 1,2-diaminobenzocrown with 1,2-bis(1H-pyrrol-2-yl)ethanedione (20). A single crystal X-ray diffraction analysis of the 18-crown-6-dipyrrolylquinoxaline 1 revealed that this molecule forms a tetramer centered around a single molecule of water, with no fewer than 10 hydrogen bonds holding the supramolecular structure together. In the case of the 15crown-5-dipyrrolylquinoxaline 2, however, X-ray diffraction analysis revealed that this species exists as a dimeric pair in the solid state, with the NH protons of one pyrrole lying within hydrogen-bonding distance of two oxygen atoms on an adjacent crown ether. A second single crystal structure of 2 was solved; it demonstrated that this system is able to coordinate a potassium cation, thereby forming an intermolecular sandwich complex, at least in the solid state. In [D6]acetone solution receptor 2 and congeners 1, 3 and 4 were also found to complex sodium and potassium cations within the crown diethyl ether binding sites, in a 1:1 manner as judged by 1H NMR spectroscopic analyses. Although systems 1-4 appear to bind fluoride anion as well as cations, the inability to obtain quantitative binding affinities of 1-4 with fluoride anion rendered the evaluation of the systems for cooperative binding impossible. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Water-Soluble Phthalocyanines Containing Aza-Crown Ether Substituents

A straightforward and generalizable synthesis of metal-free and metal (Ni, Pb, Lu) derivatives of symmetrically tetrasubstituted phthalocyanines derived from 15,16-dibromo- or -dicyano-2,3,6,7,8,9,11,12-octahydro-5H-benzotetroxazacyclopentadecine (1) is described.Quaternazation of the N-acetyl derivatives 7 in a chloroform/dimethyl sulfate mixture gives phthalocyanines 9 soluble in the pH range of 1 - 13.The electronic spectra of the phthalocyanines in buffered solutions (pH 4, 7, and 10) are examined.Furthermore, the electronic spectra of lutetium bis(phthalocyaninate) 9d in water and in DMSO are compared for the first time. Key Words: Aza-crown ethers / Phthalocyanines, amphiphilic / Quaternary lutetium bis(phthalocyaninates) / Quaternarization of acetyl amines / Lutetium complexes