Cyclen Property

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

10.53±0.20(Predicted)

form 

Crystalline Powder

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)

Safety

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

26-36

RIDADR 

1759

WGK Germany 

3

RTECS 

XA5253000

F 

3-9-34

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

II

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H311Toxic in contact with skin

H314Causes severe skin burns and eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Cyclen Chemical Properties,Usage,Production

Chemical Properties

almost white to slightly yellow crystalline powder, soluble in methanol, ethanol, dmso and other organic solvents, derived from stephania cepharantha.

Uses

Cyclen is an azamocrocycle, which can be used in the development of fluorescent nanosensors for the detection of metal ions.

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

Not classified

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.
wiki/Cyclen