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339652

Sigma-Aldrich

Cyclen

97%

Synonym(s):

1,4,7,10-Tetraazacyclododecane

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About This Item

Empirical Formula (Hill Notation):
C8H20N4
CAS Number:
294-90-6
Molecular Weight:
172.27
Beilstein:
606114
MDL number:
MFCD00066281
UNSPSC Code:
12162002
PubChem Substance ID:
24860658
NACRES:
NA.23

Assay

97%

form

solid

mp

110-113 °C (lit.)

SMILES string

C1CNCCNCCNCCN1

InChI

1S/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2

InChI key

QBPPRVHXOZRESW-UHFFFAOYSA-N

General description

Cyclen is a microcyclic tetramine that can be used as a ligand that forms a co-ordination linkage with the surface metal cations. It can be used as a synthetic precursor. It can be prepared by S-alkylation of dithiooxamide with an excess amount of bromoethane.

Application

Cyclen is an azamocrocycle, which can be used in the development of fluorescent nanosensors for the detection of metal ions.

Signal Word

Danger

Hazard Statements

H302,H311,H314,H410

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Choy Theng Loh et al.
Bioconjugate chemistry, 24(2), 260-268 (2013-01-09)
Pseudocontact shifts (PCS) from paramagnetic lanthanide ions present powerful long-range structural restraints for structural biology by NMR spectroscopy, but site-specific tagging of proteins with lanthanides remains a challenge, as most of the available lanthanide tags require proteins with single cysteine
Novel" multipoint" molecular recognition of nucleobases by a new zinc (II) complex of acridine-pendant cyclen (cyclen= 1, 4, 7, 10-tetraazacyclododecane)
Shionoya M, et al.
Journal of the American Chemical Society, 116(9), 3848-3859 (1994)
Michael A Caldwell et al.
RSC advances, 10(15), 8994-8999 (2020-04-11)
Differences in tissue pH can be diagnostic of cancer and other conditions that shift cell metabolism. Paramagnetic probes are promising tools for pH mapping in vivo using magnetic resonance spectroscopy (MRS) as they provide uniquely shifted MR signals that change
A new synthesis of cyclen (1, 4, 7, 10-tetraazacyclododecane)
Weisman GR and Reed DP
The Journal of Organic Chemistry, 61(15), 5186-5187 (1996)
Jennifer K Molloy et al.
Organic & biomolecular chemistry, 10(2), 314-322 (2011-11-11)
The design and synthesis of dinuclear-lanthanide complexes possessing triazole-based bridges, formed by using copper catalysed 1,3-cycloaddition reactions between heptadentate alkyne functionalised cyclen europium or terbium complexes and di-azides (CuAAC reactions), are described. While this click reaction worked well for the
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