N,N,N',N'-Tetrakis(3-aminopropyl)-1,4-butanediamine

• CAS: 120239-63-6
• Catalog Number: ACM120239636-2
• Category: Main Products
• Molecular Weight: 316.53g/mol
• Molecular Formula: C16H40N6
• Synonyms: 1,4-Butanediamine, N,N,N',N'-tetrakis(3-aminopropyl)-
• IUPAC Name: N,N,N',N'-tetrakis(3-aminopropyl)butane-1,4-diamine
• Canonical SMILES: C(CCN(CCCN)CCCN)CN(CCCN)CCCN
• InChI: InChI=1S/C16H40N6/c17-7-3-13-21(14-4-8-18)11-1-2-12-22(15-5-9-19)16-6-10-20/h1-20H2
• InChI Key: LYBWJVKFJAIODE-UHFFFAOYSA-N
• Appearance: Brown oil
• Complexity: 177
• Covalently-Bonded Unit Count: 1
• EC Number: 601-687-5
• Exact Mass: 316.331445g/mol
• Formal Charge: 0
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Heavy Atom Count: 22
• Monoisotopic Mass: 316.331445g/mol
• Rotatable Bond Count: 17
• UNII: E66EU344PY
• XLogP3: -1.3

Case Study

N,N,N',N'-Tetrakis(3-Aminopropyl)-1,4-Butanediamine for the Synthesis of Cationic Polymers

Santamarina, S. C., et al. Synthesis of Cationic Polymers Based on Porphyrins for Photoinactivation of Bacteria. 2021, 3, x.

The synthesis of porphyrin-based cationic polymers can be achieved in a rapid and simple manner via nucleophilic aromatic substitution (SNAr). In the prepared PZnTPPF polymers, the porphyrin units retain their properties as photosensitizers (PSs) with potential applications in the formation of photoactive sterile surfaces.
Synthesis procedure of PZnTPPF polymers
· Synthesis of the 5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin (TPPF20) involved an acid catalyzed condensation reaction between pentafluorobenzaldehyde and pyrrole with the help of BF3·OEt2 in dichloromethane.
· The subsequent oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone resulted in a 38% yield of TPPF20. This porphyrin was then metallated with Zn(II) acetate by dissolving 58 mg (0.01 mmol) of it in 10 mL of DCM. Addition of 5 mL of a saturated solution of Zn(II) acetate in methanol, followed by stirring the mixture under argon at room temperature for 2 h, led to the formation of complex ZnTPPF20.
· Two polymers, PTPPF-16 and PZnTPPF-16, were obtained through aromatic nucleophilic substitution, using N,N,N',N'-Tetrakis(3-aminopropyl)-1,4-butanediamine as the dendrimeric structure. The reaction was conducted at room temperature for 44 h in N,N-dimethylformamide, then heated at 80°C for 4 h, achieving 100% conversion. The polymers were purified by precipitation in water and washing the solid with petroleum ether.

Preparation Strategy of DAB-Am-4-Based Chemical Sensors

Manish Khandelwal, et al. Journal of Fluorine Chemistry, 2012, 135, 339-343.

N,N,N',N'-Tetrakis(3-aminopropyl)-1,4-butanediamine(DAB-Am-4) is a flexible four-arm polypropylene imine tetraamine dendrimer. The DAB-Am-4 core was successfully connected to the chromophore (aza group) through the urea moiety to prepare a colorimetric sensor 1 for fluoride ion. The connection of DAB-Am-4 to a fluorophore (naphthyl) of similar components can obtain a colorimetric sensor 2, which shows excellent binding constants with pyrophosphate anions.
Preparation procedure of DAB-Am-4 based colorimetric receptors
· The DAB-Am-4 (N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine) was refluxed with corresponding isocyanates (4-isocyanato-4'-nitroazobenzene or naphthyl isocyanate) in dry acetonitrile at 90 °C for 8 h under inert atmosphere with the 1:4 molar ratios. The titled compounds were isolated (N1,N1,N4,N4-tetrakis(3-(N'-(1-(4-nitrophenyl)-2-phenyldiazenyl)-ureido)propyl)butane-1,4-diamine (1) and N1,N1,N4,N4-tetrakis(3-(N'-naphthyl-ureido)propyl)butane1,4-diamine (2)), purified and characterized by NMR ( 1 H and 13C), MS (FAB) and elemental analysis.
· The results showed that sensor 1 could effectively recognize biologically important F^- and HP₂O₇^3- anions. While receptor 2 could serve as a selective sensor for F^- and HP₂O₇^3- anions.