35980-67-7

Basic information

• Product Name: 1,5,9-Triazacyclododecane, 1,5,9-tris[(4-methylphenyl)sulfonyl]-
• CAS NO: 35980-67-7
• Molecular Formula: C30H39N3O6S3
• Molecular Weight: 633.854
• Mol File: 35980-67-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,5,9-Triazacyclododecane, 1,5,9-tris[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5,9-Triazacyclododecane, 1,5,9-tris[(4-methylphenyl)sulfonyl]-(35980-67-7)
• EPA Substance Registry System: 1,5,9-Triazacyclododecane, 1,5,9-tris[(4-methylphenyl)sulfonyl]-(35980-67-7)

Safety Data

• Hazardous Substances Data: 35980-67-7(Hazardous Substances Data)

Upstream product

• 53364-99-1 N,N'-ditoluenesulfonyl-1,3-diaminopropane 
• 75321-10-7 3-propyl tosylate 
• 5469-66-9 propane-1,3-diol ditosylate 
• 56187-12-3 N-tosyl-bis(3-hydroxypropyl)amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 35980-64-4 1,5,9-Tritosyl-1,5,9-triazanonane 
• 109-64-8 1,3-dibromo-propane 
• 3518-88-5 3,3'-imino-di-propionic acid diethyl ester 
• 5446-58-2 3,3'-iminodipropanoic acid tosylamide 
• 56-18-8 bis(3-aminopropyl)amine 

Downstream Products

• 35980-62-2 1,5,9-triazacyclododecane trihydrobromide 
• 294-80-4 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.

MACROHETEROCYCLES. 15.* SYNTHESIS OF MACROCYCLIC POLYAMINES IN A BIPHASIC SYSTEM

Macrocyclic polyamines are conveniently synthesized by condensation of bissulfonamides with ditosylates or dibromides of glycols in the biphasic system toluene(xylene)-aqueous sodium hydroxide.

MACROHETEROCYCLES. PART 44. FACILE SYNTHESIS OF AZACROWN ETHERS AND CRYPTANDS IN A TWO-PHASE SYSTEM

A facile procedure is proposed for the preparation of azacrown ethers and cryptands by condensation of dibromides or ethylene glycol bis(toluene-p-sulphonate)s with acyclic bis(sulphonamide)s or with bisdiazacrown ethers, respectively.The reaction was carried out in a two-phase system of aqueous alkali-toluene (benzene)in the presence of quaternary ammonium salts as phase transfer catalysts.The catalytic activity decreased in the sequence: Bu4NI ca.Bu4NBr > Bu4NCl > Bu4NHSO4 > Et3NCH2C6H5NCl.Maximum yields of twelve-membered azacrown ethers are obtained when lithium hydroxide is used, while crown ethers of larger size are observed in the presence of sodium or potassium hydroxides; this may be due to a template effect.