259160
1,4,8,11-Tetraazacyclotetradecane
98% (GC)
Synonym(s):
Cyclam
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About This Item
Empirical Formula (Hill Notation):
C10H24N4
CAS Number:
Molecular Weight:
200.32
Beilstein:
111811
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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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
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
Abir El Majzoub et al.
Inorganic chemistry, 50(9), 4029-4038 (2011-04-12)
The coordination properties and the photophysical response of a new cyclam fluorescent probe for Zn(II), [L1H: 1-(benzimidazol-2-ylmethyl]-1,4, 8,11-tetraazacyclotetradecane] toward Cu(II), Zn(II), and Cd(II) are reported. The stability constants of the corresponding complexes were determined by means of potentiometric measurements in
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
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