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

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

Uses

Used in Chemical Research:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione is used as a ligand for metal complexes in chemical research for its high affinity for metal ions, which allows for the formation of stable complexes.
Used in Catalysis:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione is used as a catalyst in various chemical reactions due to its ability to form stable complexes with metal ions, enhancing the efficiency and selectivity of the reactions.
Used in Metal Extraction:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione is used in metal extraction processes for its high affinity for metal ions, enabling efficient separation and recovery of valuable metals.
Used in Medical Imaging:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione is used in medical imaging as a chelating agent to bind and stabilize metal ions, improving the contrast and resolution of imaging techniques.
Used in Antimicrobial Applications:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione derivatives are used as antimicrobial agents, exhibiting potential activity against various microorganisms, which can be useful in the development of new antibiotics.
Used in Anticancer Applications:
1,4,8,11-Tetraazacyclotetradecane-5,7-dione derivatives are used as anticancer agents, showing potential in targeting and killing cancer cells, which can contribute to the development of novel cancer therapies.

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

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

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.

Kinetics and mechanism of the acid dissociation of copper (II) complex of novel C-functionalized macrocyclic dioxotetraamines

The kinetics of the acid dissociation of copper(II) complex of a novel C-functionalized macrocyclic dioxotetraamine has been studied using a stopped-flow spectrophotometer. It was proven that substituents decrease the acid dissociation rates. The dissociation rate follows the law vd = CcomkK1K2H2/ (1 + K1H + K1K2H2). On the intermediates we have obtained, the dissociation kinetics are interpreted by a mechanism involving the negatively charged carbonyl oxygen of the complex being rapidly protonated in a pre-equilibrium step, the rate-determining step being intramolecular hydrogen(enolic tautomer) migration(to imine nitrogen). The dissociation rate reached a plateau in strongly acidic solution. By means of temperatures coefficient method, K1, K2 of the pre-equilibrium step and ΔH≠ and ΔS≠ of the rate-determining step were obtained and the results discussed. It is the strong in-plane ligand field that increased ΔH of the rate-determining step and thus decreases the dissociation rate constant. The Broensted type linear free energy relationships do exist in this C-functionalized dioxotetraamine copper(II) complex. The results clarify insights into acid dissociation mechanisms for the 14-membered macrocyclic dioxotetraamine copper(II) complex.

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.