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Merck
CN

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:
295-37-4
Molecular Weight:
200.32
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24855689
EC Number:
206-039-1
Beilstein/REAXYS Number:
111811
MDL number:
MFCD00005105

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InChI key

MDAXKAUIABOHTD-UHFFFAOYSA-N

InChI

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

SMILES string

C1CNCCNCCCNCCNC1

assay

98% (GC)

mp

184-186 °C (lit.)

Related Categories

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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX6563
MKCX1975
MKCX0407
MKCX0406
MKCX0405

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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)
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
Novel Zn (II) complexes with non-steroidal anti-inflammatory ligand, flufenamic acid: Characterization, topoisomerase I inhibition activity, DNA and HSA binding studies.
Smolkova R, et al.
Journal of Inorganic Biochemistry, 177(17), 143-158 (2017)
Luis G Alves et al.
Dalton transactions (Cambridge, England : 2003), 41(47), 14288-14298 (2012-10-09)
Novel Bn(2)Cyclam-based zirconium complexes of the type (Bn(2)Cyclam)Zr(X)(X') (3, X = X' = OPh; 4, X = X' = SPh; 5, X = Cl, X' = O(i)Pr) were synthesized in good yields via metathesis routes involving the reaction of the
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