182316-06-9

Basic information

• Product Name: 1,5,9-Triazacyclododecane, 3-methylene-1,5-bis[(4-methylphenyl)sulfonyl]-
• CAS NO: 182316-06-9
• Molecular Formula: C24H33N3O4S2
• Molecular Weight: 491.676
• Mol File: 182316-06-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,5,9-Triazacyclododecane, 3-methylene-1,5-bis[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5,9-Triazacyclododecane, 3-methylene-1,5-bis[(4-methylphenyl)sulfonyl]-(182316-06-9)
• EPA Substance Registry System: 1,5,9-Triazacyclododecane, 3-methylene-1,5-bis[(4-methylphenyl)sulfonyl]-(182316-06-9)

Safety Data

• Hazardous Substances Data: 182316-06-9(Hazardous Substances Data)

Upstream product

• 182316-08-1 9-benzyl-3-hydroxymethyl-1,5-bis(4-methylbenzenesulfonyl)-1,5,9-triazacyclododecane 
• 182316-10-5 9-benzyl-3-chloromethyl-1,5-ditosyl-1,5,9-triazacyclododecane 
• 100-44-7 benzyl chloride 
• 1555-71-1 N1-(3-amino-propyl)-N1-benzyl-propane-1,3-diamine 
• 47771-56-2 N⁴-benzyl-N¹,N⁷-ditosyl-4-aza-1,7-heptanediamine 
• 782-87-6 N-benzylbis(2-cyanoethyl)amine 
• 111-94-4 3,3'-Iminodipropionitrile 
• 182316-44-5 9-benzyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane (CADA) 
• 182316-12-7 3-chloromethyl-1,5-ditosyl-1,5,9-triazacyclododecane 

Relevant articles and documents

Syntheses, conformations, and basicities of bicyclic triamines

The multistep syntheses of several bicyclic triamines are described, all of which have an imbedded 1,5,9-triazacyclododecane ring. In 1,5,9-triazabicyclo[7.3.3]pentadecanes 12, 13, 15, and 16, two nitrogens are bridged by three carbons. The monoprotonated forms of these triamines are highly stabilized by a hydrogen-bonded network involving the bridge and both bridgehead nitrogens, producing a difference of more than 8 pKa units in acidities of their monoprotonated and diprotonated forms. The one- and zero-carbon bridges in 1,5,9-triazabicyclo[9.1.1]tridecane (23) and 7-methyl-1,5,9-triazabicyclo[5.5.0]dodecane (39) do not enhance the stabilities of their monoprotonated forms. X-ray crystal structures and computational studies of 12·HI and 16·HI reveal similar, but somewhat weaker, hydrogen-bonded networks, relative to 15·HI. The activation free energies for conformational inversion of 13·HI (14.4 ± 0.2 kcal/mol), 16·HI (15.0 ± 0.1 kcal/mol) and 16 (8.8 ± 0.3 kcal/mol) were measured by variable-temperature 1H and 13C NMR spectroscopy. These experimental barriers give an estimate of 6.2 kcal/mol for the strength of the bifurcated hydrogen bond between the bridge nitrogen and cavity proton in 16·HI. Computational studies support the hypothesis that N-inversion occurs in an open conformation, leading to an estimate of 10.32 kcal/mol for the enthalpy of the bifurcated hydrogen bond in 16·HI in the gas phase.