41757-95-3

Usage

Uses

Used in Ion-Selective Electrodes and Sensors:
4'-Acetylbenzo-15-crown-5-ether is utilized as a selective agent in ion-selective electrodes and sensors, capitalizing on its ability to selectively bind specific metal ions. This property is crucial for the development of sensitive and accurate sensors for detecting and measuring metal ion concentrations in various environments.
Used in Chemical Extraction and Separation Processes:
In the field of chemical extraction and separation, 4'-Acetylbenzo-15-crown-5-ether serves as a key component in processes that require the selective separation of metal ions from complex mixtures. Its selective binding capabilities facilitate the efficient and targeted extraction of specific ions, improving the overall efficiency and selectivity of these processes.
Used in Pharmaceutical and Biomedical Applications:
4'-Acetylbenzo-15-crown-5-ether finds application in the pharmaceutical and biomedical sectors, where its metal ion binding properties can be harnessed for the development of new drugs or diagnostic tools. 4'-ACETYLBENZO-15-CROWN 5-ETHER may be integrated into drug delivery systems or used as a component in the design of novel therapeutic agents targeting metal ion-related diseases or conditions.
Used in Catalysis:
In the realm of catalysis, 4'-Acetylbenzo-15-crown-5-ether is employed as a catalyst or a catalyst support, leveraging its ability to selectively bind metal ions to enhance the efficiency and selectivity of various chemical reactions. This can lead to improved reaction outcomes and more sustainable catalytic processes.
Used as a Chemical Reagent in Organic Synthesis:
4'-Acetylbenzo-15-crown-5-ether also serves as a valuable chemical reagent in organic synthesis, where its unique structure and metal ion binding properties can be exploited to facilitate specific synthetic transformations or to enable the formation of complex organic molecules with high precision and selectivity.

InChI:InChI=1/C16H22O6/c1-13(17)14-2-3-15-16(12-14)22-11-9-20-7-5-18-4-6-19-8-10-21-15/h2-3,12H,4-11H2,1H3

Upstream product

• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 
• 1197-09-7 1-(3,4-dihydroxyphenyl)ethan-1-one 
• 75906-43-3 1-(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-ethanone oxime 
• 14098-44-3 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 120-80-9 benzene-1,2-diol 
• 75-36-5 acetyl chloride 
• 112-60-7 Tetraethylene glycol 
• 55400-73-2 ((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate 

Downstream Products

• 76177-49-6 5<(benzo-15-crown-5)-4'-yl>pyrazine-2,3-dicarbonitrile 
• 39557-70-5 4'-Vinylbenzo-15-crown-5 ether 
• 934244-62-9 C₂₄H₃₁N₃O₅S 
• 934244-61-8 C₂₄H₃₁N₃O₅S 
• 934244-60-7 C₂₄H₃₁N₃O₅S 
• 1393674-39-9 C₂₃H₂₉N₃O₇ 
• 1254227-97-8 16,16-diphenyl-2,3,5,6,8,9,11,12-octahydro-16H-[1,4,7,10,13]pentaoxacyclopentadeca[2,3-g]chromene 
• 85921-13-7 6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecene-2-carboxylic acid (4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 56683-56-8 methyl (benzo-15-crown-5)-15-carboxylate 
• 77586-31-3 4'-(N-isopropylbenzylaminoacetoxy)benzo-15-crown-5 hydrochloride 
• 77586-30-2 4'-(N-methylbenzylaminoacetoxy)benzo-15-crown-5 hydrochloride 
• 77586-32-4 4'-(N-t-butylbenzylaminoacetoxy)benzo-15-crown-5 hydrochloride 

Relevant academic research and scientific papers

Solvent Extraction of Lanthanoid(III) Picrates with a Bis(crown ether): Enhanced Extractability through Double-sandwich Complexation

Solvent extractions of aqueous light lanthanoid(III) picrates (La-Gd) with 1,8-dioxooctamethylenebis(4'-benzo-15-crown-5) 4 were conducted at low ionic strength in the absence of dense background salts.Possessing two crown ether units, the bis(crown ether) gave much higher extractabilities for the lanthanoids than did the reference ligand, 4'-acetylbenzo-15-crown-5 3, or related ligands 15-crown-5 1 and benzo-15-crown-5 2, although the profile of the relative cation-selectivity sequence became flat.Unexpectedly, quantitative solvent extraction studies revealed that the cation:ligand stoichiometry of the complex is not 1:1 but 1:2.This indicates that the enhanced extractabilities and the decreased cation selectivity arise not from the conventional intramolecular sandwich complexation but from the unique bimolecular double-sandwich complexation incorporating four crown ether units wrapping around a partially hydrated lanthanoid ion that has to be shielded effectively from the surrounding organic solvent molecules.

Benzo-15-crown-5-Aluminium Chloride Complexes of Unusual Stability

Among twelve crown ethers of 12, 15, 18, and 21 rings only benzo-15-crown-5 and those with an electron-releasing substituent formed the complexes with aluminium chloride which were stable in methanol.

Heterogeneous catalytic acylation of benzo crown ether using acetic anhydride

Benzo-15-crown-5 macrocycle has been acetylated using acetic anhydride and a series of cation exchanged clays. This acetylating method has great advantages such as the significant reduction of the formation of by-products lower price and the possibility of environmental friendly process. Yields as high as 80% for the acetylated compound are reached in short times.

Lipase-mediated resolution of racemic benzo-15-crown-5 ether derivatives

Racemic large secondary alcohol, 4'-hydroxyethyl-benzo-15-crown-5-ether, (±)-1 was kinetically resolved in high optical yield by asymmetric transformation with Candida antarctica lipase and Pseudomonas cepacia lipase. (C) 2000 Elsevier Science Ltd.

EFFECT OF GUEST CATION ON THE PHOTOREACTIVITY OF THE PYRAZINE DERIVATIVES HAVING CROWN ETHER MOIETY

Irradiation of the acetonitrile solution of 4'-(5,6-dicyanopyrazin-2-yl)benzo-15-crown-5 (1) or 4-(5,6-dicyanopyrazin-2-yl)-1,2-dimethoxybenzene (2) in the presence of triethylamine gave monodecyano-derivative (3 or 4) and bisdecyano-derivative (5 or 6).S

Studies on the photochemical behavior of N-salicylidenaniline in chloroform

An N-salicylidenaniline (SA), compound 1 with 15-crown-5 moiety, was synthesized. The time-dependent NMR was used to track its photochromic process. The experimental results showed that ultraviolet irradiation would lead compound 1 to decompose into the corresponding salicylaldehyde and amine in chloroform solution, instead of experiencing a photochromic process. By the same method, the reported photochromic results of other SAs were also corrected.

Synthesis and characterization of new vic-dioximes with benzo-15-crown-5 derivatives and their nickel(II), copper(II), cobalt(II) complexes

Benzo-15-crown-5-p-toluidino-glyoxime (1) and N(1-naphthyl)amino-benzo-15- crown-5-glyoxime (2) were synthesized by classical methods. Their structures were confirmed by spectral techniques. Both of them were capable of forming complexes with various metal ions (Co2+, Cu2+ and Ni 2+). The structure of the complexes was confirmed by FT-IR, mass spectra and elemental analyses.

Synthesis, metal ion binding, and photochromic properties of benzo- and naphthopyrans annelated by crown ether moieties

Combining a photochromic chromene with a crown ether moiety results in systems in which photochromism and ionophoric properties could significantly influence each other. In this paper, we report the synthesis of several chromenes annelated by 15(18)-crown

Acetylation of B15C5 crown ether on Cu modified clay catalysts

With different copper-clay based catalysts, in the presence of AcCl as acetylation agent, B15C5 crown ether is acetylated in a convenient heterogeneous catalytic procedure. We show here the first heterogeneous catalytic method for crown ether acylation, where the Cu exchanged clay gives the best results using really catalytic amount of catalyst.

Preparation and Characterization of Tetraaza[14]annulene and its Nickel(II) and Copper(II) Complexes with Crown Ether Functionalities

Three new organic hosts are described that contain a tetraaza[14]annulene core to which two crown ether voids are attached. These hosts include a free base tetraaza[14]annulene and/or its complexes with benzo-15-crown-5 rings. The crown tetraaza[14]annulene is synthesized from tetraaza[14]annulene and 4′-chloroformylbenzo-15-crown-5. Its nickel(II) and copper(II) complexes are prepared in a similar manner as above. In solution the compounds do not tend to form aggregates. However, aggregation is affected by the presence of alkali-metal salts, which coordinate to the crowns. Li+ and Na+ cations with diameters that match the diameters of the crown ether rings form 1:2 host-guest complexes. Complexes with 2:2 host-guest stoichiometry are formed when the diameters of K+ and Cs+ cations exceed that of the crown ether rings. Nevertheless, it is weak for the present macrocycle and its complexes to be inclined to form dimers owing to the steric hindrance of the substituent groups and owing to restraining the rotation of the carbonyl bond connecting the crown ether group.