63972-19-0

Basic information

• Product Name: 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE
• Synonyms: 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE;DIOXOCYCLAM;1,4,8,11-Tetraazacyclotetradecane-5,7-dione 99%;1,4,8,11-tetrazacyclotetradecane-5,7-dione
• CAS NO: 63972-19-0
• Molecular Formula: C₁₀H₂₀N₄O₂
• Molecular Weight: 228.29
• Mol File: 63972-19-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 172-176 °C(lit.)
• Boiling Point: 552.1 °C at 760 mmHg
• Flash Point: 234.8 °C
• Appearance: /
• Density: 1.012 g/cm³
• Vapor Pressure: 3.09E-12mmHg at 25°C
• Refractive Index: 1.442
• BRN: 1214926
• CAS DataBase Reference: 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE(63972-19-0)
• EPA Substance Registry System: 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE(63972-19-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 63972-19-0(Hazardous Substances Data)

Usage

General Description

1,4,8,11-Tetraazacyclotetradecane-5,7-dione, also known as cyclam, is a cyclic compound containing four nitrogen atoms and a dione functional group. It is an important chelating agent, with a high affinity for metal ions such as copper, nickel, and zinc. Cyclam is widely used in chemical research as a ligand for metal complexes, as well as in various industrial and medical applications. Its ability to form stable complexes with metal ions makes it useful for catalysis, metal extraction, and medical imaging. Additionally, cyclam derivatives have shown potential as antimicrobial and anticancer agents, further expanding its potential uses in the fields of medicine and biotechnology.

InChI:InChI=1/C10H20N4O2/c15-9-8-10(16)14-7-5-12-3-1-2-11-4-6-13-9/h11-12H,1-8H2,(H,13,15)(H,14,16)

Upstream product

• 4741-99-5 3,7-diazanonane-1,9-diamine 
• 105-53-3 diethyl malonate 
• 136537-72-9 AuCl₂(NHCOCH₂CONHC₂H₄NHC₃H₆NHC₂H₄)⁽¹⁺⁾*AuCl₄^(1-)={AuCl₂(NHCOCH₂CONHC₂H₄NHC₃H₆NHC₂H₄)}(AuCl₄) 

Downstream Products

• 117152-73-5 1,11-N,N'-bis(p-toluenesulphonyl)-1,4,8,11-tetraazacyclotetradecane 
• 123530-21-2 1,11-Bis-(toluene-4-sulfonyl)-1,4,8,11-tetraaza-cyclotetradecane-5,7-dione 
• 136368-53-1 1,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-5,7-dione 

Relevant articles and documents

cis-Dioxocyclam

Molecules of 1,4,8,11-tetraazacyclotetradecane-5,7-dione, or cis-dioxocyclam, C10H20N4O2, lie across mirror planes in space group Cmca; the crystal structure reveals interleaved columns of cis-dioxocyclam molecules along the 21 screw axis parallel to the crystallographic b axis. The columns are interconnected in a chain-like arrangement by an amido hydrogen-bonding network (N...O = 2.816 A) and an amino hydrogen-bonding network (N...N = 3.193 A). The intracolumn spacing is 9.02 A.

The first gold(III) macrocyclic polyamine complexes and application to selective gold(III) uptake

The hitherto unreported gold(III) macrocyclic polyamine complexes 12, 14, 18, 19, 23, and 24 with cyclam (1,4,8,11-tetraazacyclotetradecane, 1), phenol-pendant cyclam 2, pyridyl-pendant cyclam 3, monooxocyclam 4, phenol-pendant monooxocyclam 5, and pyridyl-pendant monooxocyclam 6 have been synthesized and characterized. Dissociation of a proton from one of the secondary amines in the AuIII-in cyclam complexes 12, 14, and 18 readily occurs with pKa values of 5.0-5.4 at 25°C and I = 0.1 (NaClO4). Although monooxocyclam 4 does not accommodate Au(III), the donor-pendant monoxocyclams 5 and 6 enclose Au(III) with concomitant dissociation of an amide proton to yield 23 and 24, respectively. As anticipated for the diamagnetic d8 complexes, the pendant donors only weakly interact from an axial site. The extraordinary acidity of Au(III) over other common metal ions in interaction with cyclam can be utilized for selective uptake of Au(III) with lipophilic cyclam derivatives 9 and 10.