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259160

Sigma-Aldrich

1,4,8,11-Tetraazacyclotetradecane

98% (GC)

Synonyme(s) :

Cyclam

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About This Item

Formule empirique (notation de Hill):
C10H24N4
Numéro CAS:
295-37-4
Poids moléculaire :
200.32
Numéro Beilstein :
111811
Numéro CE :
206-039-1
Numéro MDL:
MFCD00005105
Code UNSPSC :
12352005
ID de substance PubChem :
24855689
Nomenclature NACRES :
NA.22

Pureté

98% (GC)

Pf

184-186 °C (lit.)

Chaîne SMILES 

C1CNCCNCCCNCCNC1

InChI

1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2

Clé InChI

MDAXKAUIABOHTD-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
MKCX0407
MKCX0406
MKCX0405
MKCR3837
MKCQ0355

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Michael Schmittel et al.
Chemical communications (Cambridge, England), 48(96), 11730-11732 (2012-10-20)
The two states of a new nanomechanical switch were quantitatively and reversibly populated in several subsequent switching cycles using either Cu(+) or cyclam as chemical inputs. State II was demonstrated to cis-trans isomerise diazastilbene upon irradiation selectively in the presence
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)
Jing Li et al.
Biomacromolecules, 13(10), 3220-3227 (2012-09-26)
A series of reducible polycationic copper chelators (RPCs) based on 1,4,8,11-tetraazacyclotetradecane (cyclam) were synthesized by Michael addition. Molecular weight of the polycations was controlled by reaction stoichiometry and reaction conditions, resulting in polymers with molecular weights ranging from 4400 to
Cyclam (1,4,8,11-tetraazacyclotetradecane) with one methylphosphonate pendant arm: a new ligand for selective copper (II) binding.
F?zerova S, et al.
Dalton Transactions, 2908-2915 (2005)
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