97565-24-7

Basic information

• Product Name: 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE
• Synonyms: 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE;1,4,8,11-tetrazacyclotetradecane-5,12-dione
• CAS NO: 97565-24-7
• Molecular Formula: C₁₀H₂₀N₄O₂
• Molecular Weight: 228.29
• Mol File: 97565-24-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 552.1°Cat760mmHg
• Flash Point: 234.8°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 3.09E-12mmHg at 25°C
• Refractive Index: 1.442
• CAS DataBase Reference: 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE(97565-24-7)
• EPA Substance Registry System: 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE(97565-24-7)

Safety Data

• Hazardous Substances Data: 97565-24-7(Hazardous Substances Data)

Usage

General Description

1,4,8,11-Tetraaza-cycotetradecane-5,12-dione, also known as Cyclam, is a chemical compound with a cyclic structure and four nitrogen atoms. It is commonly used as a chelating agent in coordination chemistry to form complexes with metal ions. Cyclam has a high affinity for metal ions such as copper, nickel, and cobalt, and can be used in various applications, including catalysis, medicinal chemistry, and materials science. Its complexation properties also make it useful in environmental and biological studies. Additionally, Cyclam has potential applications in drug delivery and as a contrast agent in biomedical imaging.

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

Upstream product

• 107-15-3 ethylenediamine 
• 292638-85-8 acrylic acid methyl ester 
• 29094-08-4 N-(2-Aminoethyl)-β-alanine 

Downstream Products

• 188640-01-9 1,1'-m-xylylbis(1,4,8,11-tetraazacyclotetradecane-5,12-dione) 
• 188640-00-8 1,1'-m-xylylbis(8-tert-butyloxycarbonyl-1,4,8,11-tetraazacyclotetradecane-5,12-dione) 
• 1013930-96-5 1,8-bis-(4-[2,2';6',2'']terpyridin-4'-yl-benzyl)-1,4,8,11-tetraazacyclotetradecan-5,12-dione 
• 1266336-95-1 1,8-[N,N-bis(3-formyl-12-hydroxy-5-bromo)benzyl]-5,12-dioxo-1,4,8,11-tetraazacyclotetradecane 
• 1266336-94-0 1,8-[N,N-bis(3-formyl-12-hydroxy-5-methyl)benzyl]-5,12-dioxo-1,4,8,11-tetraazacyclotetradecane 
• 1266336-96-2 N,N-bis[1,8-dibenzoyl]-5,12-dioxo-1,4,8,11-tetraazacyclotetradecane 
• 1266336-98-4 N,N-bis[1,8-bis(4-nitrobenzoyl)]-5,12-dioxo-1,4,8,11-tetraazacyclotetradecane 
• 1266336-97-3 N,N-bis[1,8-bis(2-nitrobenzoyl)]-5,12-dioxo-1,4,8,11-tetraazacyclotetradecane 

Relevant articles and documents

Synthesis, characterization and X-ray crystal structures of cyclam derivatives. Part IV. 1,4,8,11-Tetraazacyclotetradecane-5,12-dione and its diprotonated forms

The synthesis, spectroscopic characterization (NMR, IR, MS) and protonation constants of a dioxocyclam derivative, 1,4,8,11-tetraazacyclotetradecane-5,12-dione (1), are described. The crystal structures of the free-base macrocycle and two diprotonated forms, with bromide and perchlorate as counter ions, have been determined by X-ray diffraction studies in order to evaluate the influence of both the secondary amine's protonation state and of the intermolecular hydrogen-bonding interactions on the macrocycle conformation. The spectroscopic, potentiometric and structural data indicate that both secondary amines behave independently from each other, their protonation inducing only limited conformational changes of the macrocyclic framework. In the crystal, the diprotonated species adopt two different [3,4,3,4] diamond-lattice-type conformations as a consequence of intermolecular hydrogen bonds involving the oxo groups and the surrounding anions.

Copper(n) complexes of the isomeric tetraazamacrocyclic ligands 1,11- And l,8-bis(2-pyridylmethyl)-l,4,8,ll-tetraazacyclotetradecane and of the 1,4,8,1 l-tetraazacyclotetradecane-5,12-dione analogue at neutral and basic pH

The regioselective synthesis of the new N,N'-dialkylated tetraazamacrocycle 1,1 l-bis(2-pyridylmethyl)-l,4,8,l 1tetraazacyclotetradecane, L1, has been achieved. The copper(n) complexes of L1 and of the isomeric ligand l,8-bis(2pyridylmethyl)-1,4,8,11-tetr