1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane Chemical Properties

Melting point:

>236°C (dec.)

Boiling point:

767.4±60.0 °C(Predicted)

Density 

1.211±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Water (Slightly, Heated, Sonicated)

form 

Solid

pka

15.76±0.40(Predicted)

color 

White to Off-White

Sensitive 

Hygroscopic

InChI

InChI=1S/C16H32N8O4/c17-13(25)9-21-1-2-22(10-14(18)26)5-6-24(12-16(20)28)8-7-23(4-3-21)11-15(19)27/h1-12H2,(H2,17,25)(H2,18,26)(H2,19,27)(H2,20,28)

InChIKey

FQIHLPGWBOBPSG-UHFFFAOYSA-N

SMILES

N1(CC(N)=O)CCN(CC(N)=O)CCN(CC(N)=O)CCN(CC(N)=O)CC1

1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane Usage And Synthesis

Uses

DOTAM, can be used in the prepataion of Gadolinium(III) Complexes for Magnetic Resonance Imaging (MRI).

Synthesis

General procedure for the synthesis of 2,2',2'',2''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetra)tetraacetamide from 2-bromoacetamide and rotenone: In a 100 mL round-bottomed flask fitted with a reflux condenser and stirring bar, 1.4696 g of rotenone (8.5 mmol) was added. A mixture of 5.44 g 2-bromoacetamide (39.4 mmol, 4.6 eq.) and 4.5748 g triethylamine (44.9 mmol, 5.3 eq.) dissolved in 30 mL of anhydrous ethanol was subsequently added. The reaction mixture was refluxed at 80 °C for 4 h. A white precipitate gradually formed in the flask during the reaction. Upon completion of the reaction, the reaction was cooled to room temperature, the precipitate was decanted and transferred to a 250 mL round bottom flask. The precipitate was dissolved in 200 mL of hot 80% ethanol/20% water solvent mixture. The volume of the solution was concentrated to approximately 30% of the original volume using a rotary evaporator and the concentrate was subsequently placed in a refrigerator overnight to precipitate white crystals. The crystals were separated by filtration, transferred to a 50 mL round bottom flask and dried under vacuum on a Schlenk line for several hours to give the target product in 66% yield. The product was characterized by ESI-MS and NMR (1H NMR and 13C NMR): ESI-MS: m/z = 401.3 (100%), 402.3 (15%) [M + H]+; 423.4 (25%), 424.4 (<10%) [M + Na]+. 1H NMR (500 MHz, D2O), δ (ppm): 3.02 (s, amide side chain CH2, 8H), 2.57 (s, rotary tannin ring CH2, 16H).13C NMR (125 MHz, D2O), δ (ppm): 174.07 (carbonyl carbon), 55.86 (amide CH2), 50.42 (cyclic CH2).

References

[1] Patent: WO2015/38943, 2015, A1. Location in patent: Page/Page column 51; 52
[2] Angewandte Chemie, 1994, vol. 106, # 7, p. 824 - 826
[3] Helvetica Chimica Acta, 2005, vol. 88, # 5, p. 923 - 935

1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane(157599-02-5)Related Product Information

• Tetradecane
• 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane
• N,N,N'-tris(2-aminoethyl)ethylenediamine
• 3,6,10,13,16,19-Hexaazabicyclo(6.6.6)eicosane-1,8-diamine
• CB-Cyclam(M-200)
• CB-TE2A