1,3,5-TRIS(AMINOMETHYL)-2,4,6-TRIETHYLBENZENE

• CAT Number: M097646
• CAS Number: 149525-65-5
• Molecular Formula: C15H27N3
• Molecular Weight: 249.40
• Purity: ≥95%
• Synonyms: (2,4,6-Triethylbenzene-1,3,5-triyl)trimethanamine
• Storage: -20°C
• IUPAC Name: [3,5-bis(aminomethyl)-2,4,6-triethylphenyl]methanamine
• InChI: InChI=1S/C15H27N3/c1-4-10-13(7-16)11(5-2)15(9-18)12(6-3)14(10)8-17/h4-9,16-18H2,1-3H3
• InChIKey: DBOPPHIBSRVLLK-UHFFFAOYSA-N
• SMILES: CCC1=C(C(=C(C(=C1CN)CC)CN)CC)CN

1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene（Cat No.:M097646） is a synthetic organic compound characterized by a benzene ring substituted with both aminomethyl and ethyl groups. The structure includes three aminomethyl groups attached to the carbon atoms at positions 1, 3, and 5, and three ethyl groups at positions 2, 4, and 6. This symmetrical arrangement provides multifunctional capabilities, crucial for applications in polymer chemistry and material science. The presence of multiple amino groups makes it an excellent candidate for cross-linking, potentially enhancing the properties of polymers such as durability, chemical resistance, and thermal stability.

Reference

[1]. J Org Chem. 2017 Dec 15;82(24):13368-13375. doi: 10.1021/acs.joc.7b02447. Epub 2017 Dec 5.
Synthesis, Anion Recognition, and Transmembrane Anionophoric Activity of Tripodal Diaminocholoyl Conjugates.
Li Z(1), Yu XH(1), Chen Y(1), Yuan DQ(2), Chen WH(1).
Author information: (1)Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University , Guangzhou 510515, P.R. China. (2)Faculty of Pharmaceutical Sciences, Kobe Gakuin University , Minatojima 1-1-3, Chuo-ku, Kobe 650-8586, Japan.
In this paper, we present the synthesis, anion recognition, and anionophoric activity of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene-based tripodal 3α-hydroxy-7α,12α-diamino-5β-cholan-24-oate conjugate 1 and the corresponding tris(2-aminoethyl)amine-based analogue 2 and choloyl analogue 3. Their affinity toward anions was evaluated by means of competitive displacement assay using 5-carboxyfluorescein (5-FAM) as a fluorescent indicator. The results indicate compounds 1 and 2 exhibit strong recognition toward a wide range of biologically important anions, in particular, toward sulfate and phosphate anions. In MeOH-HEPES (4/1, pH 7), the binding constants of compounds 1 and 2 are 416- and 168-fold higher for sulfate than for chloride and 35- and 25-fold higher for phosphate than for chloride, respectively. The anion transport activity was measured by use of pH discharge assay and chloride-ion-selective electrode technique. The results indicate that compounds 1 and 2 function as effective anion-selective transporters in the order of ClO4- > I- > NO3- > Br- > Cl- > SO42- > H2PO4- and exhibit anionophoric activity via a process of major anion exchange and minor anion/cation symport. In addition, some insights into the correlation of the anion binding affinity with the transport efficiency are also briefly discussed.
DOI: 10.1021/acs.joc.7b02447 PMID: 29164882

[2]. J Pept Sci. 2010 Sep;16(9):465-72. doi: 10.1002/psc.1262.
Convergent synthesis of a helical, prehairpin HR1 trimer from HIV gp41.
Lu RJ(1), Mader CJ, Schneider SE, Tvermoes N, Kang MC, Dwyer JJ, Wilson KL, Matthews TJ, Delmedico MK, Bray B.
Author information: (1)Trimeris, Inc., 3500 Paramount Parkway, Morrisville, NC 27560, USA.
A helical, prehairpin trimer covering the majority of the HR1 region of human immunodeficiency virus gp41 was achieved by chemically coupling three identical 51 amino acid peptides. A 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene pinwheel 'cap' was used to trimerize the peptides by taking advantage of the unique property of triacyl fluoride and orthogonal protection and deprotection. The resulting protein is fully helical, highly thermostable and soluble.
DOI: 10.1002/psc.1262 PMID: 20629115 [Indexed for MEDLINE]

[3]. Chem Commun (Camb). 2015 Sep 28;51(75):14235-8. doi: 10.1039/c5cc05737j. Epub 2015 Aug 11.
Sterically geared tris-thioureas; transmembrane chloride transporters with unusual activity and accessibility.
Valkenier H(1), Dias CM, Porter Goff KL, Jurček O, Puttreddy R, Rissanen K, Davis AP.
Author information: (1)School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. .
Tris-N-arylthioureas derived in one step from 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene are remarkably effective anion carriers. With optimised aryl substituents their activities come close to the best currently known, suggesting that they might find use as readily available standards in anion transport research.
DOI: 10.1039/c5cc05737j PMID: 26260730 [Indexed for MEDLINE]