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295-37-4 - 1,4,8,11-Tetraazacyclotetradecane, 98+% - Cyclam - A11516 - Alfa Aesar

A11516 1,4,8,11-Tetraazacyclotetradecane, 98+%

CAS Number
295-37-4
Synonyms
Cyclam

Size Price ($) Quantity Availability
1g 58.50
5g 201.60
25g 691.48
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1,4,8,11-Tetraazacyclotetradecane, 98+%

MDL
MFCD00005105
EINECS
206-039-1

Chemical Properties

Formula
C10H24N4
Formula Weight
200.33
Melting point
184-188°
Sensitivity
Air Sensitive
Solubility
Soluble in water.

Applications

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.

Notes

Hygroscopic. Incompatible with oxidizing agents.

Literature 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.

/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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
111811
Harmonized Tariff Code
2933.99
TSCA
No
RTECS
XA5254800

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