Cyclen

Cyclen
  • CAS No.:294-90-6
Other grades of this product :
Cyclen Basic information
Product Name:Cyclen
Synonyms:Cyclen,97%;Kryptofix 11 aza;10-Tetraazacyclododecane;Cyclen(M-100);Tetraaza-12-Crown-4 ( CYclen);1,4,7,10-tetrazacyclododecane {Cyclene);Tetraazacyclododecane (Cyclen);Cyclen, 97% 250MG
CAS:294-90-6
MF:C8H20N4
MW:172.27
EINECS:608-365-3;425-450-9
Product Categories:API;Crown Ethers;Functional Materials;organic amine;Heterocycles;Intermediates & Fine Chemicals;Macrocycles for Host-Guest Chemistry;Ring Systems;Pharmaceuticals;Other APIs;Achiral Nitrogen;Cy-N;294-90-6
Mol File:294-90-6.mol
Cyclen Chemical Properties
Melting point 110-113 °C (lit.)
Boiling point 292.61°C (rough estimate)
density 1.0415 (rough estimate)
vapor pressure 0.004Pa at 20℃
refractive index 1.5872 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Crystalline Powder
pka10.53±0.20(Predicted)
color Almost white to slightly yellow
Water Solubility almost transparency
BRN 606114
Stability:hygroscopic
InChIKeyQBPPRVHXOZRESW-UHFFFAOYSA-N
LogP-0.63 at 20℃
CAS DataBase Reference294-90-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/38-36/37/38
Safety Statements 26-36
RIDADR 1759
WGK Germany 3
RTECS XA5253000
3-9-34
Hazard Note Irritant
HazardClass 8
PackingGroup II
HS Code 29339900
MSDS Information
ProviderLanguage
Cyclen English
SigmaAldrich English
ACROS English
Cyclen Usage And Synthesis
Chemical Propertiesalmost white to slightly yellow crystalline powder, soluble in methanol, ethanol, dmso and other organic solvents, derived from stephania cepharantha.
UsesCyclen is an azamocrocycle, which can be used in the development of fluorescent nanosensors for the detection of metal ions.
ApplicationCyclen (1,4,7,10-tetraazacyclododecane) is a macrocyclic aza analogue of the crown ether 12-crown-4. Cyclen compounds are capable of selectively binding cations and are used as a ligand with chemicals used in MRI contrast (as well ass other imaging) agents.
Synthesis Reference(s)Journal of the American Chemical Society, 96, p. 2268, 1974 DOI: 10.1021/ja00814a056
General DescriptionCyclen 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.
Flammability and ExplosibilityNotclassified
SynthesisSome syntheses exploit the Thorpe-Ingold effect to facilitate ring-formation. Illustrative is the reaction of the deprotonated tosylamides with ditosylates: TsN(CH2CH2NTsNa)2 + TsN(CH2CH2OTs)2 → (TsNCH2CH2)4The resulting macrocycle can be deprotected with strong acid. Base gives the tetramine. High dilution conditions result in a low reaction rate penalty and this disadvantage is removed in an alternative procedure starting from triethylenetetraamine and dithiooxamide to a bisamidine – also a bis(imidazoline) – followed by reduction and ring expansion with DIBAL. In one study cyclen is covalently bonded through a propylene molecular spacer to adenine and chelated with zinc diperchlorate. This complex is able to selectively bind uracil and uridine in a 1:2 ratio both through the adenine part and cyclen part of the molecule as evidenced by mass spectrometry. wiki/Cyclen

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