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. | + | 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
| 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): | |
| LD50 (Median dose)
|
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.
Contents
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.
