66750-10-5

Basic information

• Product Name: N-PHENYLAZA-15-CROWN 5-ETHER
• Synonyms: PHENYLAZA-15-CROWN-5;N-PHENYLAZA-15-CROWN-5;N-PHENYLAZA-15-CROWN 5-ETHER;N-PHENYL-13-AZA-1,4,7,10-TETRACYCLOPENTADECANE;N-PHENYL-13-AZA-1,4,7,10-TETRAOXACYCLOPENTADECANE;CROWN ETHER/N-PHENYLAZA-15-CROWN-5;LABOTEST-BB LT00441378;13-phenyl-1,4,7,10-tetraoxa-13-azacyclopentadecane
• CAS NO: 66750-10-5
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.37
• EINECS: 266-470-6
• Product Categories: Azacrown Ethers;Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry
• Mol File: 66750-10-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 46 °C
• Boiling Point: 437.06°C (rough estimate)
• Flash Point: 133.3°C
• Appearance: yellow solid
• Density: 1.0647 (rough estimate)
• Vapor Pressure: 2.94E-08mmHg at 25°C
• Refractive Index: 1.4909 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: almost transparency in Methanol
• PKA: 5.16±0.40(Predicted)
• CAS DataBase Reference: N-PHENYLAZA-15-CROWN 5-ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENYLAZA-15-CROWN 5-ETHER(66750-10-5)
• EPA Substance Registry System: N-PHENYLAZA-15-CROWN 5-ETHER(66750-10-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• Hazardous Substances Data: 66750-10-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H25NO4/c1-2-4-16(5-3-1)17-6-8-18-10-12-20-14-15-21-13-11-19-9-7-17/h1-5H,6-15H2

Upstream product

• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 80322-82-3 triethyleneglycol dimesylate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 108-86-1 bromobenzene 
• 66943-05-3 1,4,7,10-tetraoxa-15-azacyclopentadecane 
• 94342-00-4 1,8-dichloro-3,6-dioxaoctane 

Downstream Products

• 66749-93-7 13,13'-(4,4'-phenylmethanediyl-diphenyl)-bis-(1,4,7,10-tetraoxa-13-aza-cyclopentadecane) 
• 73171-45-6 C₁₉H₂₅N₅O₆S 
• 66749-96-0 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde 
• 150196-53-5 2-{2-[4-(4,7,10,13-tetraoxa-1-azacyclopentadecyl)phenyl]ethenyl}-3-(3-sulphopropyl)benzothiazolium betaine 
• 66750-07-0 13-(4-nitrosophenyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 66749-90-4 tetra-N-methyl-4,4'-[4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-phenylmethanediyl]-bis-aniline 
• 66750-12-7 4-[4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-phenylazo]-benzoic acid ethyl ester 
• 66750-13-8 13-[4-(3-nitro-phenylazo)-phenyl]-1,4,7,10-tetraoxa-13-aza-cyclopentadecane 
• 66749-97-1 13,13',13''-(4,4',4''-methanetriyl-triphenyl)-tris-(1,4,7,10-tetraoxa-13-aza-cyclopentadecane) 
• 66749-95-9 bis(4-N-phenylaza-15-C-5) methane 
• 66749-92-6 4-[4,4'-bis-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzhydryl]-N,N-dimethyl-aniline 
• 66750-11-6 13-(4-phenylazo-phenyl)-1,4,7,10-tetraoxa-13-aza-cyclopentadecane 
• 66750-14-9 4-aza-15-crown-5-4'-nitroazobenzene 

Relevant articles and documents

Efficient synthesis of N-Aryl-aza-crown ethers via palladium-catalyzed amination

N-Aryl-aza-crown ethers were efficiently prepared by reaction of an aza-crown ether with an aryl bromide via a palladium-catalyzed amination. The combination of Pd2(dba)3 and a biphenyl-based electron-rich bulky monophosphine is effective for catalyzing the coupling of 1-aza-15-crown-5 with both electron-deficient and electron-rich aryl bromides under mild conditions. N-Aryl-aza-crown ethers were produced in 75-91% yields. N-Aryl-aza-crown ethers with o-aryl substituents can also be synthesized using this catalyst system, albeit in lower yields (~40%).

A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+

A novel multi-response chemosensor L based on coumarin-chalcone-crown ether was designed and synthesized, which exhibited a high selectivity for the colorimetric detecting Al3+ and Cu2+ and fluorescent recognizing Al3+ and Mg2+ in ethanol. L can monitor Al3+ and Cu2+ via distinct color changes from a slight yellow to pink and to orange, respectively. The sensor L can also monitor Al3+ and Mg2+ by fluorescence emission responses at 592 nm and 547 nm with low detection limits of 0.31 μM and 0.23 μM, respectively. The selectivity of L toward Al3+, Cu2+ and Mg2+ was not interfered by a large number of coexisting ions and was found to be reversible. By means of spectrometric titration, Job's plot, mass spectrometry, 1H NMR titration and IR spectroscopy analysis, it was unanimously confirmed that the sensor L had a stoichiometric ratio of 1:1 with Cu2+ and Mg2+, and 1:2 with Al3+. The order of the stability of the complexes formed by L and Al3+, Cu2+, Mg2+ was as follows: L-Al3+ > L-Cu2+ > L-Mg2+. At the same time, some possible bonding modes and sensing mechanisms were further proposed, and the optimized structure of the sensor L and its sensing mechanism for Al3+, Cu2+ and Mg2+ were confirmed by the calculations of DFT/B3LYP and TD-DFT methods in a suite of Gaussian 09 programs.

Catch-Release System for Dosing and Recycling Silver(I) Catalyst with Status of Catalytic Activity Reported by Fluorescence

The silver(I) catch-release system composed of nanoswitch 1 and the anthracene-appended crown ether 2 is infallibly driven by chemical triggers and ion transfer. Any state of the silver(I) translocation is self-reported by a ratiometric emission signature at 472 and 554 nm. In the self-sorted networked state I, the silver(I) ions are tightly shielded inside nanoswitch [Ag(1)]+ ("catch") so that their catalytic activity is zero while emission at 554 nm is maximum. Addition of zinc(II) releases silver(I) from [Ag(1)]+ and generates the catalytically active and fluorescent complex [Ag(2)]+. In this networked state II ("release") both catalytic activity and emission at 472 nm are maximum. Removal of the original trigger regenerates networked state I. ON/OFF control and recycling of catalyst was demonstrated over three in situ cycles.