1,4,8,11-Tetraazacyclotetradecane, 98+%, Thermo Scientific Chemicals

Name: 1,4,8,11-Tetraazacyclotetradecane, 98+%, Thermo Scientific Chemicals
SKU: ALFA11516.06

CAS: 295-37-4 | C10H24N4 | 200.33 g/mol

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Chemical Identifiers

CAS594-39-8

IUPAC Name2-methylbutan-2-aminium

Molecular FormulaC5H14N

InChI KeyGELMWIVBBPAMIO-UHFFFAOYSA-O

SMILESCCC(C)(C)[NH3+]

Specifications

Specification Sheet

Appearance (Color)Clear colorless to pale yellow

Assay (GC)≥97.5%

Refractive Index1.3975-1.4015 @ 20°C

FormLiquid

Identification (FTIR)Conforms

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Soluble in water.

Notes
Hygroscopic. Incompatible with oxidizing agents.

RUO – Research Use Only

General 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 (Ferrocenyl methyl) trimethyl ammonium iodide, 39399.
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.