106872-64-4

Basic information

• Product Name: Benzoic acid, 4,4'-[1,6-hexanediylbis(nitrilomethylidyne)]bis-, dimethyl ester
• CAS NO: 106872-64-4
• Molecular Formula: C24H28N2O4
• Molecular Weight: 408.497
• Mol File: 106872-64-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4,4'-[1,6-hexanediylbis(nitrilomethylidyne)]bis-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4,4'-[1,6-hexanediylbis(nitrilomethylidyne)]bis-, dimethyl ester(106872-64-4)
• EPA Substance Registry System: Benzoic acid, 4,4'-[1,6-hexanediylbis(nitrilomethylidyne)]bis-, dimethyl ester(106872-64-4)

Safety Data

• Hazardous Substances Data: 106872-64-4(Hazardous Substances Data)

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 264191-33-5 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-methoxycarbonylbenzyl)-1,6-hexanediamine 
• 264191-36-8 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-azidomethylbenzyl)-1,6-hexanediamine 
• 264191-34-6 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-hydroxymethylbenzyl)-1,6-hexanediamine 
• 264191-35-7 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-chloromethylbenzyl)-1,6-hexanediamine 
• 264191-37-9 N,N'-bis(4-azidomethylbenzyl)-1,6-hexanediamine 
• 264191-32-4 N,N'-bis(4-methoxycarbonylbenzyl)-1,6-hexanediamine 

Relevant articles and documents

Neutralization of a sec-ammonium group unusually stabilized by the "rotaxane Effect": Synthesis, structure, and dynamic nature of a "free" sec-amine/crown ether-type rotaxane

A fifteen-year riddle has been settled: neutralization, the most popular chemical event, of a crown ether/sec-ammonium salt-type rotaxane has been achieved and a completely nonionic crown ether/sec-amine-type rotaxane isolated. A [2]rotaxane was prepared as a typical substrate from a mixture of dibenzo[24]crown-8 ether (DB24C8) and sec-ammonium hexafluorophosphate (PF 6) with a terminal hydroxy group through end-capping with 3,5-dimethylbenzoic anhydride in the presence of tributylphosphane as a catalyst in 90 % yield. A couple of approaches to the neutralization of the ammonium rotaxane were investigated to isolate the free sec-amine-type rotaxane by decreasing the degree of thermodynamic and kinetic stabilities. One approach was the counteranion-exchange method in which the soft counterion PF 6- was replaced with the fluoride anion by mixing with tetrabutylammonium fluoride, thus decreasing the cationic character of the ammonium moiety. Subsequent simple washing with a base allowed us to isolate the free sec-amine-type rotaxane in a quantitative yield. The other approach was a synthesis based on a protection/deprotection protocol. The acylation of the sec-ammonium moiety with 2,2,2-trichloroethyl chloroformate gave an N-carbamated rotaxane that could be deprotected by treating with zinc in acetic acid to afford the corresponding free sec-amine-type rotaxane in a quantitative yield. The structure of the free sec-amine-type rotaxane was fully confirmed by spectral and analytical data. The generality of the counteranion-exchange method was also confirmed through the neutralization of a bisammonium-type [3]rotaxane. The mechanism was studied from the proposed potential-energy diagram of the rotaxanes with special emphasis on the role of the PF 6- counterion. Neutral and free: The neutralization of the ammonium group of crown ether/sec-ammonium salt-type rotaxanes is a simple, yet important issue, which had not been solved to date. Neutral rotaxanes had not been isolated because of their unusual stability; however, the successful synthesis of free amine-type rotaxanes has now been achieved. The key to canceling this strong stabilization is the construction of a multiple equilibrium system and the successful removal of the conjugate acid from the reaction system (see scheme). Copyright