1,4,7,10-Tetraazacyclododecane

Base Information

• Chemical Name: 1,4,7,10-Tetraazacyclododecane
• CAS No.: 294-90-6
• Molecular Formula: C8H20N4
• Molecular Weight: 172.274
• Hs Code.: 29339900
• European Community (EC) Number: 425-450-9,608-365-3
• NSC Number: 629374
• UNII: 964584YO2O
• DSSTox Substance ID: DTXSID60183621
• Nikkaji Number: J530.921B
• Wikipedia: Cyclen
• Wikidata: Q416407
• Metabolomics Workbench ID: 55563
• ChEMBL ID: CHEMBL19880
• Mol file: 294-90-6.mol

Synonyms:1,4,7,10-tetraazacyclododecane;cyclen;tetraaza-12-crown-4;tris acetic acid-1,4,7,10-tetraazacyclododecane

Chemical Property of 1,4,7,10-Tetraazacyclododecane

Chemical Property:

• Appearance/Colour: off- white to slightly yellow crystalline powder
• Vapor Pressure: 0.00309mmHg at 25°C
• Melting Point: 108-113 °C
• Refractive Index: 1.5872 (estimate)
• Boiling Point: 283.8 °C at 760 mmHg
• PKA: 10.53±0.20(Predicted)
• Flash Point: 129.5 °C
• PSA: 48.12000
• Density: 0.874 g/cm³
• LogP: -0.32640
• Storage Temp.: Refrigerator
• Water Solubility.: almost transparency
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 172.16879665
• Heavy Atom Count: 12
• Complexity: 65.1

Purity/Quality:

99% ^*data from raw suppliers

Cyclen 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CNCCNCCNCCN1
• 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. Cyclen is an azamocrocycle, which can be used in the development of fluorescent nanosensors for the detection of metal ions.

Technology Process of 1,4,7,10-Tetraazacyclododecane

There total 41 articles about 1,4,7,10-Tetraazacyclododecane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.23%

cyclen-glyoxal (74199-09-0,79236-92-3) → 1,4,7,10-tetraazacyclododecan (294-90-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; bromine; In water; toluene;

Reference yield: 95.0%

1,4,7,10-tetraazacyclododecane tetrahydrochloride (10045-25-7) → 1,4,7,10-tetraazacyclododecan (294-90-6)

Guidance literature:

With hydrogenchloride;

Reference yield: 94.9%

C11H13NO2 + 3-azapentane-1,5-diamine (111-40-0,98824-35-2) → 1,4,7,10-tetraazacyclododecan (294-90-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; potassium carbonate; In 2-methyltetrahydrofuran; at 15 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;

upstream raw materials:

1,4,7,10-tetraazacyclododecane tetrahydrochloride

7-<2-(1,3-Dioxolan-2-yl)ethyl>-1,4,7,10-tetraazacyclododecane-1-carbaldehyde

cyclen tetratosylate

cis-octahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene-3,4-dione

Downstream raw materials:

1,4,7,10-tetrazatricyclo[5.5.1.0]tridecane

1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid

cis-13-1,4,7,10-tetraazatetracyclo<5.5.2.0^4,140^10,13>tetradecane

1-triphenylmethyl-1,4,7,10-tetraazacyclododecane

Refernces

• 1、 Sarma, Monima,Chatterjee, Tanmay,Das, Samar K.. "A copper-cyclen coordination complex associated with a polyoxometalate anion: Synthesis, crystal structure and electrochemistry of [Cu(cyclen)(MeCN)] [W6O19]". . p. 1114 - 1117. Retrieved 2010.
• 2、 Weisman, Gary R.,Reed, David P.. "A new synthesis of cyclen (1,4,7,10-tetraazacyclododecane)". . p. 5186 - 5187. Retrieved 1996.
• 3、 Ferrari, Marinella,Giovenzana, Giovanni B.,Palmisano, Giovanni,Sisti, Massimo. "A practical synthesis of 1,4,7,10-tetraazacyclododecane, a pivotal precursor for MRI contrast agents". . p. 15 - 21. Retrieved 2000.
• 4、 Athey, Phillip S.,Kiefer, Garry E.. "A new, facile synthesis of 1,4,7,10-tetraazacyclododecane: Cyclen". . p. 4081 - 4085. Retrieved 2002.
• 5、 -. "Preparation method of cyclen and intermediate thereof". . . Retrieved 2021/07/08.
• 6、 -. "Preparation method of cycleanine". Paragraph 0031-0050. . Retrieved 2020/02/10.