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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

Certificats d'analyse (COA)

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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
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)
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
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)
Apurba Kalita et al.
Inorganic chemistry, 50(23), 11868-11876 (2011-11-02)
The nitric oxide reactivity of two copper(II) complexes, 1 and 2 with ligands L(1) and L(2), respectively, [L(1) = 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, L(2) = 5,5,7-trimethyl-[1,4]-diazepane] have been studied. The copper(II) center in complex 1 was found to be unreactive toward nitric oxide
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