1,4,8,11-tetraazacyclotetradecane

• ChemBase ID: 87525
• Molecular Formular: C10H24N4
• Molecular Mass: 200.32436
• Monoisotopic Mass: 200.20009679
• SMILES: N1CCNCCCNCCNCCC1
• Canonical SMILES: C1CNCCNCCCNCCNC1
• InChI: InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2
• InChIKey: MDAXKAUIABOHTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4,8,11-tetraazacyclotetradecane
• IUPAC Traditional name: cyclam
• Synonyms: Cyclam; 1,4,8,11-Tetraazacyclotetradecane 98%; Cyclam; 1,4,8,11-Tetraazacyclotetradecane; 1,4,8,11-Tetraazacyclotetradecane; 1,4,8,11-四氮环十四烷; 1,4,8,11-四氮杂环十四烷; 1,4,8,11-四氮环十四烷

Database IDs

• CAS Number: 295-37-4
• EC Number: 206-039-1
• MDL Number: MFCD00005105
• Beilstein Number: 111811
• PubChem SID: 24855689; 162074565
• PubChem CID: 64964
• CHEBI ID: 37401
• CHEMBL: 125150
• Chemspider ID: 58489
• Wikipedia Title: Cyclam

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -8.574456
• LogD (pH = 7.4): -6.0942044
• Log P: -1.3376942
• Molar Refractivity: 60.6284 cm^3
• Polarizability: 24.545666 Å^3
• Polar Surface Area: 48.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 5 g/100 mL (20 °C) in water
• Melting Point: 184-186 °C(lit.); 184-188°C; 185 - 188°C; 185-190 °C

Safety Information

• Storage Warning: Air Sensitive
• RTECS: XA5254800
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.0% (NT); 98%; 98+%
• Grade: purum
• Ignition Residue: ≤1%
• Empirical Formula (Hill Notation): C10H24N4

DETAILS

Sigma Aldrich - 259160

General description
Metal complexes of azamacrocycles are often more stable in vitro alternatives to open chain ligands.
Packaging
1, 5 g in poly bottle

Sigma Aldrich - 86725

Other Notes
Synthesis of aza-macrocycles with pendant arms1,2,3,4

REFERENCES

• Nitrogen analogue of the crown ethers (see Appendix 2), forming stable complexes with metal ions: Inorg. Chem., 4,1102, 1109 (1965); Can. J. Chem., 48, 1481 (1970). For examples of use as a versatile ligand in coordination chemistry, see: Acc. Chem. Res., 11, 392 (1978); J. Chem. Soc., Chem. Commun., 1322 (1986); 1075 (1987); 156 (1988); Inorg. Chem., 26, 908 (1987); J. Am. Chem. Soc., 110, 3679 (1988).
• Complex with iron(II) triflate is an effective epoxidation catalyst: J. Am. Chem. Soc., 113, 7052 (1991).
• The Ni(II) complex catalyzes the novel electrochemical reaction of epoxides with carbon dioxide to give good yields of cyclic carbonates: J. Chem. Soc., Chem. Commun., 43 (1995). A similar system catalyzes the electrochemical intramolecular reductive cyclization of a series of o-halogenated aryl alkenes: Tetrahedron Lett., 36, 4429 (1995):
  
• For use in synthesis of molecules with electroactive cavities, see (Ferrocenylmethyl)trimethylammonium iodide, 39399.