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Sigma-Aldrich

Cyclen tetrahydrochloride

98%

Synonym(s):

1,4,7,10-Tetraazacyclododecane tetrahydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H20N4 · 4HCl
CAS Number:
10045-25-7
Molecular Weight:
318.11
MDL number:
MFCD00068484
UNSPSC Code:
12352100
PubChem Substance ID:
24867136
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

mp

>293 °C (dec.) (lit.)

SMILES string

Cl[H].Cl[H].Cl[H].Cl[H].C1CNCCNCCNCCN1

InChI

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

InChI key

SBWLCGZEBQGYRP-UHFFFAOYSA-N

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General description

Cyclen tetrahydrochloride is a macrocycle hydrochloride salt. It can be synthesized using perhydro-2a,4a,6a,8a-tetraazacyclopenteno[1,3-f,g]acenaphthylene as a precursor. Cyclen tetrahydrochloride has an orthorhombic crystal structure. Cations are reported to exhibit crystallographic two-fold rotation symmetry and [3333] quadrangular conformation, having protonated N atoms at corner positions. Synthesis of cyclen from the corresponding butanedione-protected linear tetramines has been reported.

Application

Cyclen tetrahydrochloride may be used for the synthesis of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methyleneethylphosphinic acid), a new macrocyclic polyaza polyphosphinate ligand. It may also be used in the synthesis of anthraquinone-pendant cyclen.

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Zinc (II)-Cyclen Complex Attached to an Anthraquinone Moiety that Acts as a Redox-Active Nucleobase Receptor in Aqueous Solution.
Tucker JHR, et al.
Bulletin of the Chemical Society of Japan, 68(9), 2465-2469 (1995)
A Simple Synthesis of the Macrocycle 1,4,7,10-Tetraazacyclododecane.
Sandnes RW, et al.
Acta Chemica Scandinavica, 52(12), 1402-1404 (1998)
A new route to cyclen, cyclam and homocyclen.
Herve G, et al.
Tetrahedron Letters, 39(38), 6861-6864 (1998)
Synthesis and complexation properties of a new macrocyclic polyaza polyphosphinate ligand, DOTEP (1, 4, 7, 10-tetraazacyclododecane-1, 4, 7, 10-tetrakis (methyleneethylphosphinate)).
Lazar I, et al.
Inorganic Chemistry, 30(26), 5016-5019 (1991)
Structure of 1, 4, 7, 10-tetraazacyclododecane tetrahydrochloride.
Reibenspies JH and Anderson OP.
Acta Crystallographica Section C, Crystal Structure Communications, 46(1), 163-165 (1990)

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