| Identification | More | [Name]
Cyclen | [CAS]
294-90-6 | [Synonyms]
1,4,7,10-TETRAAZACYCLODODECANE
CYCLEN
1,4,7,10-Tetrazacyclododecane
1,4,7,10-Tetracyclododecane
Tetraaza 12-crown-4
1,4,7,10-Tetraazacyclododecane,min.98%CYCLEN
1,4,7,10-TETRAAZACYCLODODECANE(CYCLEN)
1,4,7,10-Tetraazacyclododecane 98%
Cyclen ( 1,4,7,10-Tetraaza Cyclododecane)
1,4,7,10-TETRAAZACYCLODODECANE, 98.5%
1,4,7,10-TETRAAZACYCLODODECANEHCL
1,4,7,10-Tetraazacyclododecane( Cyclenine ) | [EINECS(EC#)]
202-928-3 | [Molecular Formula]
C8H20N4 | [MDL Number]
MFCD00066281 | [Molecular Weight]
172.27 | [MOL File]
294-90-6.mol |
| Chemical Properties | Back Directory | [Appearance]
ALMOST WHITE TO SLIGHTLY YELLOW CRYSTALLINE POWDER | [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. ]
Refrigerator | [form ]
Crystalline Powder | [pka]
10.53±0.20(Predicted) | [color ]
Almost white to slightly yellow | [Water Solubility ]
almost transparency | [BRN ]
606114 | [Stability:]
hygroscopic | [InChIKey]
QBPPRVHXOZRESW-UHFFFAOYSA-N | [LogP]
-0.63 at 20℃ | [CAS DataBase Reference]
294-90-6(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
1759 | [WGK Germany ]
3
| [RTECS ]
XA5253000
| [F ]
3-9-34 | [Hazard Note ]
Irritant | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29339900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Hydrochloric acid-->Ethyl acetate-->Sulfuric acid-->Acetic acid-->Pyridine-->Sodium Methoxide-->Tosyl chloride-->Diethanolamine-->Diisopropyl ether-->Diethylenetriamine-->1,4,7,10-TETRA-P-TOSYL-1,4,7,10-TETRAAZACYCLODODECANE-->1-Bromo-2-iodoethane-->1,4,7,10-TETRAAZACYCLODODECANE TETRAHYDROCHLORIDE-->1-Bromo-2-chloroethane-->1,2-DIIODOETHANE-->1,2-Dibromoethane | [Preparation Products]
TRI-TERT-BUTYL 1 4 7 10-TETRAAZACYCLODOD-->Ethylenediamine-->DOTA |
| Hazard Information | Back Directory | [Chemical Properties]
ALMOST WHITE TO SLIGHTLY YELLOW CRYSTALLINE POWDER | [Uses]
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. | [Application]
Cyclen (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. | [Definition]
ChEBI: 1,4,7,10-tetraazacyclododecane is an azacycloalkane that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogen atoms. It is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 96, p. 2268, 1974 DOI: 10.1021/ja00814a056 | [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. | [Flammability and Explosibility]
Notclassified | [Synthesis]
Some 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)4
The 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.
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