1,4,8,11-Tetraazaundecane

Last updated
1,4,8,11-Tetraazaundecane
2,32-tet.svg
Names
IUPAC name
N,N'-Bis(2-aminoethyl)propane-1,3-diamine
Other names
2,3,2-Tet, N,N′-bis(2-aminoethyl)-1,3-propanediamine
Identifiers
3D model (JSmol)
1742732
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.022.958 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 225-254-1
27228
PubChem CID
UNII
  • InChI=1S/C7H20N4/c8-2-6-10-4-1-5-11-7-3-9/h10-11H,1-9H2
    Key: UWMHHZFHBCYGCV-UHFFFAOYSA-N
  • C(CNCCN)CNCCN
Properties
C7H20N4
Molar mass 160.265 g·mol−1
Appearancecolorless oil
Density 0.9501
Boiling point 80–82 °C (176–180 °F; 353–355 K) 20 Torr
Hazards
GHS labelling:
GHS-pictogram-acid.svg
Danger
H314
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,4,8,11-Tetraazaundecane, IUPAC name: N,N'-bis(2-aminoethyl)propane-1,3-diamine, is the organic compound with the formula (H2NCH2CH2NHCH2)2CH2. It is a tetramine, consisting of two primary amines and two secondary amines positioned symmetrically. Like many amines, this compound has a high affinity for carbon dioxide. [1] The compound can be prepared by treatment of 1,3-dibromopropane with excess ethylenediamine. [2]

The compound has been examined often as a ligand in coordination chemistry. It is tetradentate ligand similar to 1,4,7,10-tetraazadecane. [3] By condensation of its nickel(II) complexes with formaldehyde, one can obtain a variety of macrocyclic ligands. [4]

Structure of [Cu(1,4,8,11-tetraazaundecane)(H2O)] . Color code: red = O, blue = N, white = C. CSD CIF BEKTIY.png
Structure of [Cu(1,4,8,11-tetraazaundecane)(H2O)] . Color code: red = O, blue = N, white = C.

References

  1. ↑ Puxty, Graeme; Rowland, Robert; Allport, Andrew; Yang, Qi; Bown, Mark; Burns, Robert; Maeder, Marcel; Attalla, Moetaz (2009). "Carbon Dioxide Postcombustion Capture: A Novel Screening Study of the Carbon Dioxide Absorption Performance of 76 Amines". Environmental Science & Technology. 43 (16): 6427–6433. Bibcode:2009EnST...43.6427P. doi:10.1021/es901376a. PMID   19746747.
  2. ↑ Van Alphen, J. (1936). "On Aliphatic Polyamines III". Recueil des Travaux Chimiques des Pays-Bas. 55 (10): 835–840. doi:10.1002/recl.19360551004.
  3. ↑ Bosnich, B.; Gillard, R. D.; McKenzie, E. D.; Webb, G. A. (1966). "Steric constraints imposed on facultative ligands. Complexes of triethylenetetramine and a homologue". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 1331. doi:10.1039/J19660001331.
  4. ↑ De Blas, Andrés; De Santis, G.; Fabbrizzi, L.; Licchelli, Maurizio; Pallavicini, P. (1993). "Novel routes to functionalized cyclam-like macrocycles". Pure and Applied Chemistry. 65 (3): 455–459. doi:10.1351/pac199365030455.
  5. ↑ Tsymbal, Liudmyla V.; Arion, Vladimir B.; Lampeka, Yaroslaw D. (2022). "Synthesis and crystal structure of trans -diaqua(1,4,8,11-tetraazaundecane)copper(II) isophthalate monohydrate". Acta Crystallographica Section E: Crystallographic Communications. 78 (8): 851–854. Bibcode:2022AcCrE..78..851T. doi:10.1107/S2056989022007538. PMC   9361364 . PMID   35974816.
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