Difference between revisions of "Cyclen"

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==Preparation==
 
==Preparation==
Cyclen is prepared from [[diethylenetriamine]] and [[diethanolamine]], using [[tosyl chloride]] to introduce a tosyl protecting group for amines. [[Sodium ethoxide]] is used to convert the tosyl diethylenetriamine into its sodium salt which reacts with the diethanolamine. The reaction takes place in anhydrous [[Dimethylformamide|DMF]]. [[Sulfuric acid]] is used to remove the tosyl groups, then the compound is converted into freebase and purified.
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Cyclen is prepared from [[diethylenetriamine]] and [[diethanolamine]], using [[4-Toluenesulfonyl chloride|tosyl chloride]] to introduce a tosyl protecting group for amines. [[Sodium ethoxide]] is used to convert the tosyl diethylenetriamine into its sodium salt which reacts with the diethanolamine. The reaction takes place in anhydrous [[Dimethylformamide|DMF]]. [[Sulfuric acid]] is used to remove the tosyl groups, then the compound is converted into freebase and purified.
  
 
==Projects==
 
==Projects==

Latest revision as of 18:43, 24 January 2022

Cyclen
Names
IUPAC name
1,4,7,10-Tetrazacyclododecane
Properties
C8H20N4
(CH2CH2NH)4
Molar mass 172.276 g/mol
Appearance White solid
Odor Odorless
Melting point 110–113 °C (230–235 °F; 383–386 K)
Boiling point 272.7–285.5 °C (522.9–545.9 °F; 545.8–558.6 K)
15.8 g/100 ml (20 °C)
Solubility Reacts with acids
Hazards
Safety data sheet Sigma-Aldrich
Lethal dose or concentration (LD, LC):
200 - 2,000 mg/kg (rat, oral)
Related compounds
Related compounds
Cyclam
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclen (IUPAC: 1,4,7,10-tetraazacyclododecane) is an aza-crown ether with the formula (CH2CH2NH)4.

Properties

Chemical

Cyclen will form coordination complexes with transition metal salts.

Physical

Cyclen is a colorless white solid.

Availability

Cyclen is sold by chemical suppliers, though it's not cheap.

Preparation

Cyclen is prepared from diethylenetriamine and diethanolamine, using tosyl chloride to introduce a tosyl protecting group for amines. Sodium ethoxide is used to convert the tosyl diethylenetriamine into its sodium salt which reacts with the diethanolamine. The reaction takes place in anhydrous DMF. Sulfuric acid is used to remove the tosyl groups, then the compound is converted into freebase and purified.

Projects

  • Metal-cyclam complexes
  • Compound collecting

Handling

Safety

There is little available data on the toxicity of cyclen, but, like all amines, it should be handled with care.

Storage

In closed bottles, away from light and acids.

Disposal

Can be neutralized by destroying it using an oxidizing mixture.

References

Relevant Sciencemadness threads