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1,4,8,11-Tetraazacyclotetradecane is used in the synthesis of molecules with electroactive cavities. It acts as a nitrogen crown ether analogue and as an antioxidant in rubber. It is also used in the preparation of plerixafor derivatives.
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./n
Misra, A. C.; Luker, K. E.; Durmaz, H.; Luker, G. D.; Lahann, J. CXCR4-Targeted Nanocarriers for Triple Negative Breast Cancers. Biomacromolecules 2015, 16 (8), 2412-2417.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.