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259160 Sigma-Aldrich

1,4,8,11-Tetraazacyclotetradecane

98% (GC)

Synonym: Cyclam

  • CAS Number 295-37-4

  • Empirical Formula (Hill Notation) C10H24N4

  • Molecular Weight 200.32

  •  Beilstein/REAXYS Number 111811

  •  EC Number 206-039-1

  •  MDL number MFCD00005105

  •  PubChem Substance ID 24855689

  •  NACRES NA.22

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Properties

Related Categories ATRP, ATRP Ligands, Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers,
assay   98% (GC)
mp   184-186 °C (lit.)
SMILES string   C1CNCCNCCCNCCNC1
InChI   1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2
InChI key   MDAXKAUIABOHTD-UHFFFAOYSA-N

Description

General description

1,4,8,11-Tetraazacyclotetradecane is an azamacrocycle that forms more stable metal complexes as compared to open chain ligands.

Application

1,4,8,11-Tetraazacyclotetradecane (cyclam) can be used as a ligand in the synthesis of:
• Cyanide-bridged FeIII-CuII complexes.
• Zinc fenamate complexes [Zn(cyclam)(fen)2] possessing antimicrobial properties, fen = fenamic acid.
• Zn(II) complexes with flufenamic acid (flu), [Zn(cyclam)(flu)2].
• Polyoxometalate-metal organic extended framework, for example [{Cu(cyclam)}3(W7O24)].15.5.H2O.

Packaging

1, 5 g in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
XA5254800
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

A micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization

Reversible addition/fragmentation chain transfer (RAFT) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteri...
Keywords: Biomaterials, Living polymerization, Nanotechnology, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, transformation

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

In 2006, Matyjaszewski and co-workers first described controlled radical polymerization by Activators ReGenerated by Electron Transfer Atom Transfer Radical Polymerization (ARGET ATRP),1-3 a developm...
Keywords: Antimicrobials, Ligands, Nanotubes, Oxidations, Polymerization reactions, Radical polymerization, Reductions, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization, Solvents

Concepts and Tools for RAFT Polymerization

Reversible addition/fragmentation chain transfer (RAFT) is a form of living radical polymerization. RAFT polymerization was discovered at CSIRO in 1998.1 It soon became the focus of intensive researc...
Keywords: Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands

Emergence of living radical polymerization mediated by transition metal catalysts in 1995 was a seminal piece of work in the field of synthetic polymer chemistry.1-3 Since this date, many transition ...
Keywords: Catalysis, Condensations, Evaporation, Filtration, Ligands, Oxidations, Polymer science, Polymerization reactions, Precipitation, Purification, Radical polymerization, Reductions, Solvents

Tools for Performing ATRP (Atom Transfer Radical Polymerization)

Controlled radical polymerization (CRP) techniques have been reviewed in a number of articles1,2 and books,3 and include nitroxide-mediated polymerization (NMP),4-7 reversible addition fragmentation ...
Sebastian Grajales
Keywords: Ligands, Polymerization reactions, Purification, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization

Typical Procedures for Polymerizing via ATRP

The following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′s research group at the University of Warwick.
Keywords: Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy, Polymerization reactions, Size-exclusion chromatography, Solvents

Typical Procedures for Polymerizing via RAFT

RAFT (Reversible Addition/Fragmentation Chain Transfer) is a form of living radical polymerization involving conventional free radical polymerization of a substituted monomer in the presence of a sui...
Keywords: Nuclear magnetic resonance spectroscopy, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Peer-Reviewed Papers
15

References

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