Tris(2-pyridylmethyl)amine

Base Information

• Chemical Name: Tris(2-pyridylmethyl)amine
• CAS No.: 16858-01-8
• Molecular Formula: C18H18N4
• Molecular Weight: 290.368
• Hs Code.: 29333990
• NSC Number: 663674
• UNII: V4CE3X87Z3
• DSSTox Substance ID: DTXSID70327519
• Nikkaji Number: J633.663I
• Wikipedia: Tris(2-pyridylmethyl)amine
• Wikidata: Q7843933
• Mol file: 16858-01-8.mol

Synonyms:TPA cpd;tris(2-pyridylmethyl)amine;tris-picolylamine

Chemical Property of Tris(2-pyridylmethyl)amine

Chemical Property:

• Vapor Pressure: 6.34E-07mmHg at 25°C
• Melting Point: 85-89
• Refractive Index: 1.625
• Boiling Point: 409.8 ºC at 760 mmHg
• PKA: 4.96±0.12(Predicted)
• Flash Point: 201.6 ºC
• PSA: 41.91000
• Density: 1.175g/cm³
• LogP: 3.07400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 290.153146591
• Heavy Atom Count: 22
• Complexity: 262

Purity/Quality:

98%, ^*data from raw suppliers

tris(2-Pyridylmethyl)amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=NC(=C1)CN(CC2=CC=CC=N2)CC3=CC=CC=N3
• Uses: ATRP for Everyone: Ligands and Initiators for the Clean Synthesis of Functional Polymers

Technology Process of Tris(2-pyridylmethyl)amine

There total 15 articles about Tris(2-pyridylmethyl)amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2,4,6-trimethyl-[1,3,5]triazinane (638-14-2) + 2-chloromethylpyridine (4377-33-7) → tris[(2-pyridylmethyl)amine] (16858-01-8)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; for 2h; Reflux;

DOI:10.1039/c5dt00514k

Reference yield: 97.3%

2-chloromethylpyridine (4377-33-7) → tris[(2-pyridylmethyl)amine] (16858-01-8)

Guidance literature:

With ammonium hydroxide; N,N-dibutylpyrrolidinium bromide; at 40 ℃; for 1h; Reagent/catalyst;

Reference yield: 90.0%

pyridine-2-carbaldehyde (1121-60-4) + bis[(2-pyridyl)methyl]amine (1539-42-0) → tris[(2-pyridylmethyl)amine] (16858-01-8)

Guidance literature:

pyridine-2-carbaldehyde; bis[(2-pyridyl)methyl]amine; With acetic acid; In methanol; at 20 ℃; for 1h;

With methanol; sodium cyanoborohydride; at 0 - 20 ℃;

DOI:10.1039/d0dt00067a

upstream raw materials:

2-chloromethylpyridine

2-(Aminomethyl)pyridine

Tris(2-pyridylmethyl)ammonium perchlorate

2-(bromomethyl)pyridine hydrobromide

Downstream raw materials:

[Cu(I)(CO)(tris(2-pyridylmethyl)amine)][B(C₆F₅)4]

Fe⁽²⁺⁾*(C₅H₄NCH₂)3N*(C₆H₅COCOO)^(1-)*ClO₄^(1-)={Fe((C₅H₄NCH₂)3N)(C₆H₅COCOO)}(ClO₄)

[(tris(2-pyridylmethyl)amine)Fe(catecholate)]BPh₄

(C₁₈H₁₈N₄)Fe(C₆H₅C(O)COO)⁽¹⁺⁾*ClO₄^(1-)*CH₃OH=[(C₁₈H₁₈N₄)Fe(C₆H₅C(O)COO)](ClO₄)*CH₃OH

Refernces

• 1、 Malachowski, Mitchell R.,Huynh, Hong B.,Tomlinson, Laura J.,Kelly, Richard S.,Furbee, James W.. "Comparative Study of the Catalytic Oxidation of Catechols by Copper(II) Complexes of Tripodal Ligands". . p. 31 - 36. Retrieved 1995.
• 2、 Beni, Alessandra,Dei, Andrea,Laschi, Serena,Rizzitano, Mario,Sorace, Lorenzo. "Tuning the charge distribution and photoswitchable properties of cobalt-dioxolene complexes by using molecular techniques". . p. 1804 - 1813. Retrieved 2008.
• 3、 Bersani, Sara,Salmaso, Stefano,Mastrotto, Francesca,Ravazzolo, Elena,Semenzato, Alessandra,Caliceti, Paolo. "Star-like oligo-arginyl-maltotriosyl derivatives as novel cell-penetrating enhancers for the intracellular delivery of colloidal therapeutic systems". . p. 1415 - 1425. Retrieved 2012.
• 4、 Wang, Hongyan,Lu, Yongbin,Mijangos, Edgar,Thapper, Anders. "Photo-induced water oxidation based on a mononuclear cobalt(II) complex". . p. 467 - 473. Retrieved 2014.
• 5、 Mondal, Amit Kumar,Jover, Jesús,Ruiz, Eliseo,Konar, Sanjit. "Quantitative Estimation of Ising-Type Magnetic Anisotropy in a Family of C3-Symmetric CoII Complexes". . p. 12550 - 12558. Retrieved 2017.
• 6、 Lei, Lin,Chen, Yaju,Feng, Zhenfeng,Deng, Chunyan,Xiao, Yepeng. "Bioinspired manganese complex for room-temperature oxidation of primary amines to imines by t-butyl hydroperoxide". . . Retrieved 2021/02/21.
• 7、 Petersen, Allan R.,Lauridsen, Jerik Mathew Valera,Lee, Ji-Woong. "CO2-Controlled Reductive Amination Reactions with NaBH4". supporting information. p. 7368 - 7372. Retrieved 2020/11/30.