24772-41-6

Basic information

• Product Name: 1,5,9,13-tetraazacyclohexadecane
• Synonyms: [16]aneN4; 1,5,9,13-Tetraazacyclohexadecane; 24772-41-6
• CAS NO: 24772-41-6
• Molecular Formula: C₁₂H₂₈N₄
• Molecular Weight: 228.3775
• Mol File: 24772-41-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 359.1°C at 760 mmHg
• Flash Point: 177.4°C
• Density: 0.852g/cm³
• Vapor Pressure: 2.43E-05mmHg at 25°C
• Refractive Index: 1.426
• CAS DataBase Reference: 1,5,9,13-tetraazacyclohexadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5,9,13-tetraazacyclohexadecane(24772-41-6)
• EPA Substance Registry System: 1,5,9,13-tetraazacyclohexadecane(24772-41-6)

Safety Data

• Hazardous Substances Data: 24772-41-6(Hazardous Substances Data)

Usage

General Description

1,5,9,13-Tetraazacyclohexadecane, also known as cyclam, is a cyclic tetraamine compound with the molecular formula C10H24N4. It is a versatile ligand and forms stable complexes with metal ions, especially transition metals and lanthanides. Cyclam and its derivatives have been extensively studied and used in various fields, including medicinal chemistry, catalysis, and coordination chemistry. Its ability to chelate metal ions makes it useful in applications such as MRI contrast agents, drug delivery systems, and as a chelating agent in metal extraction processes. Cyclam and its complexes have also been investigated for their potential antibacterial, antifungal, and anticancer activities. Overall, 1,5,9,13-Tetraazacyclohexadecane is a valuable and versatile chemical with a wide range of applications in chemistry, biology, and medicine.

Upstream product

• 144534-73-6 1,5,9,13-Tetrakis-trifluoromethanesulfonyl-1,5,9,13-tetraaza-cyclohexadecane 
• 56234-53-8 1,5,9,13-tetratosyl-1,5,9,13-tetraazacyclohexadecane 
• 4605-14-5 N,N'-bis-(3-aminopropyl)-1,3-propanediamine 
• 67341-38-2 N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,3-propanediamine 
• 144534-69-0 C,C,C-Trifluoro-N-(3-trifluoromethanesulfonylamino-propyl)-N-{3-[trifluoromethanesulfonyl-(3-trifluoromethanesulfonylamino-propyl)-amino]-propyl}-methanesulfonamide 
• 60-29-7 diethyl ether 

Downstream Products

• 131426-21-6 N,N',N'',N'''-tetrakis(2-N-tosylaminoethyl)-1,5,9,13-tetra-azacyclohexaadecane 
• 133563-61-8 1-Benzyl-1,5,9,13-tetraaza-cyclohexadecane 
• 918412-00-7 ([16]aneN₄)Zn(phenylmethanethiolate) perchlorate 
• 918412-02-9 ([16]aneN₄)Zn(4-methylbenzenethiolate) perchlorate 

Relevant articles and documents

A convenient synthesis of isocyclam and [16]aneN4 and the photophysics of their dicyanochromium(III) complexes

The syntheses of the tetraazamacrocyclic ligands 1,4,7,11-tetraazacyclotetradecane (isocyclam) and 1,5,9,13-tetraazacyclohexadecane ([16]aneN4) in two steps starting from the corresponding tetraamine and diethylmalonate is reported. The trans-dicyanochromium(III) complexes, trans-[Cr(isocyclam)(CN)2]PF6 and trans-[Cr([16]aneN4)(CN)2]PF6 have also been prepared. Both are 2Eg emitters with 0-0 band emission wavelengths at 721.2 and 704.8 nm, respectively. The isocyclam complex has a room temperature excited state lifetime of 147 μs in aqueous solution which increases to 215 μs upon macrocyclic N-H deuteration, whereas the corresponding lifetime of the [16]aneN4 complex is 25 μs and is unaffected by macrocyclic N-H deuteration. The implications of the temperature dependence of the excited state lifetimes are also presented.

Triflamides for protection and cyclization of tetraamines to tetraazamacrocycles

A facile two-step synthesis of tetraazamacrocycles is reported starting from trifluoromethanesulfonyl derivatives of linear tetraamines. After cyclization, the macrocycle was deprotected using sodium in liquid ammonia.

Studies on biologically potent tetraazamacrocyclic complexes of bivalent tin

Fourteen- to eighteen-membered tetraamide macrocyclic ligands N4L1-N4L4 have been prepared by the condensation of 1,2-diaminoethane or 1,3-diaminopropane with malonic or succinic acid in the presence of condensing reagents dicyclohexylcarbodiimide and 4-dimethylaminopyridine. On reduction, these macrocyclic ligands give a new series of tetraazamacrocycles MacL1-MacL4 which form complexes with tin(II) chloride. The ligands and their complexes were characterized by elemental analyses, molecular weight determinations, infrared and 1H NMR spectral studies. The hexacoordinated state for tin has been confirmed by spectral studies. An octahedral geometry for these complexes has been proposed as the binding sites are the nitrogen atoms of the macrocycles. On the basis of the chemical composition the representation of the complexes as [Sn(MacLn)Cl2] (n = 1-4) has been established. The ligands and their complexes also have been screened for their antifungal and antibacterial activities and the findings have been reported and explained.

Methods of preparing manganese complexes of nitrogen-containing macrocyclic ligands

The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: STR1 wherein R, R', R1, R'1, R2, R'2, R3, R'3, R4, R'4, R5, R'5, R6, R'6, R7, R'7, R8, R'8, R9, and R'9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.