105400-16-6

Basic information

• Product Name: 7,16-bis{4-nitrobenzyl}-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• Synonyms: 7,16-bis{4-nitrobenzyl}-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS NO: 105400-16-6
• Molecular Formula: C₂₆H₃₆N₄O₈
• Molecular Weight: 532.58604
• Mol File: 105400-16-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7,16-bis{4-nitrobenzyl}-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 7,16-bis{4-nitrobenzyl}-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane(105400-16-6)
• EPA Substance Registry System: 7,16-bis{4-nitrobenzyl}-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane(105400-16-6)

Safety Data

• Hazardous Substances Data: 105400-16-6(Hazardous Substances Data)

Upstream product

• 23978-55-4 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 

Relevant articles and documents

Syntheses of unsymmetrically N,N′-bis (substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad

A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N′-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.

Syntheses and Binding Properties of Bibracchial Lariat Ethers (BIBLEs): Survey of Synthetic Methods and Cation Selectivities

A new, two-step method for the synthesis of 4,10-diaza-15-crown-5 and 4,13-diaza-18-crown-6 and their N,N'-disubstituted derivatives from bis(secondary amines) and 1,2-bis(2-iodoethoxy)ethane is described.Essentially, the method utilizes the incipient sidearms as nitrogen-protecting groups prior to cyclization.The yields for cyclization are high, ranging from 32percent to 77percent.The N,N'-disubstituted derivatives of 4,10-diaza-15-crown-5 produced by alkylation or acylation (A), acylation followed by reduction (AR), cyclization (C), hydrogenolysis (H), or single-step cyclization (O) have the following sidearms: H (H, 91percent), MeOCH2CH2 (C, 38percent), EtOCOCH2 (A, 62percent), PhCH2 (C,72percent), 2-MeOPh (C, 52percent), 2-furanylmethyl (C, 67percent), and 2-nitrobenzyl (A, 50percent).N,N'-Dibenzyl-4,10-diaza-18-crown-6 was obtained by cyclization in 63percent yield.The N,N'-disubstituted derivatives of 4,13-diaza-18-crown-6 produced with the new method have the following sidearms: H (H, 92percent), CO-Et (A, 100percent), n-propyl (AR, 78percent), n-butyl (C, 77percent), n-hexyl (C, 32percent; A, 50percent; O, 7percent), n-octyl (AR, 45percent), CO-n-heptyl (A, 71percent), n-nonyl (O, 11percent;A, 45percent;AR, 39percent), CO-n-undecyl (A, 87percent), n-tetradecyl (AR, 26percent), CO-n-tridecyl (A, 78percent), n-hexadecyl (A, 25percent), n-octadecyl (AR, 60percent), CO-n-heptadecyl (A, 100percent), allyl (O, 26percent), propargyl (O, 22percent), HOCH2CH2 (O, 28percent), MeOCH2CH2 (C, 43percent; AR, 76percent), HOCOCH2 (hydrolysis, 81percent), EtOCOCH2 (A, 92percent), PhCH2 (O, 29percent;C, 66percent), 2-furanylmethyl (O, 27percent, C, 62percent), 2-hydroxybenzyl (A, 85percent), 2-methoxybenzyl (O, 30percent), 2-cyanobenzyl (A, 95percent), 2-nitrobenzyl (A, 90percent), 3-nitrobenzyl (A, 95percent), and 4-nitrobenzyl (A, 70percent).The new cyclization method is compared with other, previously published cyclization reactions with respect to overall yield and ease of purification.When this new cyclization cannot be used, diaza crown ethers can be prepared by alkylation of 4,10-diaza-15-crown-5 or 4,13-diaza-18-crown-6.The homogeneous equilibrium cation binding constants (log Ks) have been determined in anhydrous methanol solution for many of the compounds described herein with Na+, K+, and Ca+.The cation selectivities are rationalized in terms of polar, structural, and lipophilicity effects.