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Sigma-Aldrich

1,4,8,11-Tetraazacyclotetradecane

98% (GC)

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Synonym(s):
Cyclam
Empirical Formula (Hill Notation):
C10H24N4
CAS Number:
295-37-4
Molecular Weight:
200.32
Beilstein:
111811
EC Number:
206-039-1
MDL number:
MFCD00005105
PubChem Substance ID:
24855689
NACRES:
NA.22

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Prasenjit Mahato et al.
Inorganic chemistry, 50(9), 4162-4170 (2011-04-01)
Two chromogenic complexes, L.Zn (where L is (E)-4-((4-(1,4,8,11-tetraazacyclotetradecan-1-ylsulfonyl)phenyl)diazenyl)-N,N-dimethylaniline) and its [2]pseudorotaxane form (α-CD.L.Zn), were found to bind preferentially to adenosine triphosphate (ATP), among all other common anions and biologically important phosphate (AMP, ADP, pyrophosphate, and phosphate) ions in aqueous HEPES
Thermally-Triggered Crystal Dynamics and Permanent Porosity in the First Heptatungstate-Metalorganic Three-Dimensional Hybrid Framework.
Martin-Caballero J, et al.
Chemistry?A European Journal , 23(59), 14962-14974 (2017)
A serials of sandwich-like trinuclear and one-dimensional chain cyanide-bridged iron (III)-copper (II) complexes: Syntheses, crystal structures and magnetic properties.
Shi J, et al.
Journal of Solid State Chemistry, 260(17), 59-66 (2018)
Jaeheung Cho et al.
Accounts of chemical research, 45(8), 1321-1330 (2012-05-23)
Metalloenzymes activate dioxygen to carry out a variety of biological reactions, including the biotransformation of naturally occurring molecules, oxidative metabolism of xenobiotics, and oxidative phosphorylation. The dioxygen activation at the catalytic sites of the enzymes occurs through several steps, such
Riccardo Ferdani et al.
Dalton transactions (Cambridge, England : 2003), 41(7), 1938-1950 (2011-12-16)
A new class of cross-bridged cyclam-based macrocycles featuring phosphonate pendant groups has been developed. 1,4,8,11-tetraazacyclotetradecane-1,8-di(methanephosphonic acid) (CB-TE2P, 1) and 1,4,8,11-tetraazacyclotetradecane-1-(methanephosphonic acid)-8-(methanecarboxylic acid) (CB-TE1A1P, 2) have been synthesized and have been shown to readily form neutral copper(II) complexes at room temperature
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