1,4,8,11-TETRAAZACYCLOTETRADECANE Chemical Properties

Melting point:

184-186 °C (lit.)

Boiling point:

328.07°C (rough estimate)

Density 

1.0203 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Dichloromethane, Methanol

pka

10.90±0.20(Predicted)

form 

Fluffy Needle-Like Crystalline Powder

color 

White

Water Solubility 

Soluble in water.

Sensitive 

Air Sensitive

BRN 

111811

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

SMILES

N1CCCNCCNCCCNCC1

CAS DataBase Reference

295-37-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

XA5254800

F 

3-9-34

HS Code 

29339900

Toxicity

LD50 intraperitoneal in mouse: 371mg/kg

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,4,8,11-TETRAAZACYCLOTETRADECANE Usage And Synthesis

Chemical Properties

white fluffy needle-like crystalline powder

Uses

Reagent used in the preparation of Plerixafor derivatives.

Uses

1,4,8,11-Tetraazacyclotetradecane is macrocyclic ligand that is used as an antioxidant in rubber and has been shown to suppress oxidation catalyzed by some metal ions.

Uses

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.

Definition

ChEBI: 1,4,8,11-tetraazacyclotetradecane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane. It derives from a hydride of a cyclotetradecane.

General Description

1,4,8,11-Tetraazacyclotetradecane is an azamacrocycle that forms more stable metal complexes as compared to open chain ligands.

Synthesis

The general procedure for the synthesis of 1,4,8,11-tetrakis[(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane from 1,4,8,11-tetrakis(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane is as follows: 1,4,8,11-tetra-tosyl-1,4,8,11-tetraazacyclotetradecane (13 mmol) was dissolved in 90% concentrated sulfuric acid, and the reaction was carried out at 100 °C The reaction was stirred for 48 hours at 100 °C. Upon completion of the reaction, the reaction mixture was cooled to 0°C. Subsequently, anhydrous ethanol (120 mL) and anhydrous ether (100 mL) were added dropwise to the reaction mixture to precipitate the solid product. The solid was collected by filtration and the filter cake was washed with a small amount of anhydrous ethanol and anhydrous ether, followed by vacuum drying. The resulting off-white solid was dissolved in 1 mol/L aqueous NaOH (90 mL) and extracted with chloroform (3 x 100 mL). The chloroform layers were combined and dried with anhydrous sodium sulfate overnight. Afterwards, the chloroform was removed by distillation under reduced pressure and the residue was vacuum dried to give a white solid product. Finally, the product was recrystallized from toluene to give 2.2 g of 1,4,8,11-tetraazacyclotetradecane in 85% yield. Mass spectral analysis of the product showed [M]+ = 200.3 m/e, 1H-NMR (400 MHz, CDCl3) δ ppm: 1.72 (t, 4H), 2.23 (s, 4H), 2.68 (s, 8H), 2.75 (t, 8H).

Purification Methods

Purify cyclam by recrystallisation from dioxane (white needles), and it sublimes above 120o. It has been distilled, b 132-140o/4-8mm. It forms complexes with metals and gives a sparingly soluble nitrate salt, m 205o(dec), which crystallises from H2O and is dried at 150o. [UV: Bosnich et al. Inorg Chem 4 1102 1963, van Alphen Recl Trav Chim Pays-Bas 56 343 1937, Beilstein 26 III/IV 1647.]

References

[1] Patent: EP2163553, 2010, A1. Location in patent: Page/Page column 18-19
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349
[5] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404

1,4,8,11-TETRAAZACYCLOTETRADECANE(295-37-4)Related Product Information

• Plerixafor 8HCl (AMD3100 8HCl)
• 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane
• 1,4,8,11-Tetrakis(dimethylaminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane
• 1,4,8,11-Tetrakis(aminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane,1,4,8,11-Tetraazacyclotetradecane-N,N',N'',N'''-tetraacetamide, min. 98%
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• 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane
• 1-Benzyl-1,4,8,11-tetraazacyclotetradecane,N-Benzyl-1,4,8,11-tetraazacyclotetradecane, min. 98%
• 1,4,8,11-Tetramethyl-1,4,8,11-tetraazacyclotetradecane,98%,1,4,8,11-TETRAMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE
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• Tetradecane
• 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE
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