Tris(4-iodophenyl)amine

Base Information

• Chemical Name: Tris(4-iodophenyl)amine
• CAS No.: 4181-20-8
• Molecular Formula: C18H12I3N
• Molecular Weight: 623.013
• Hs Code.: 29214990
• European Community (EC) Number: 631-013-5
• DSSTox Substance ID: DTXSID50430979
• Nikkaji Number: J149.789H
• Wikidata: Q72515197
• Mol file: 4181-20-8.mol

Synonyms:Tris(4-iodophenyl)amine;4181-20-8;Tris-(4-Iodophenyl)Amine;4-iodo-N,N-bis(4-iodophenyl)aniline;4,4',4''-Triiodotriphenylamine;Trisiodophenylamine;C18H12I3N;tris(p-iodophenyl)amine;SCHEMBL985323;DTXSID50430979;MFCD01321198;AKOS015853669;Triphenylamine, 4,4',4''-triiodo-;CS-W018335;SB66586;AC-24430;DS-16795;FT-0635175;T1724;Benzenamine, 4-iodo-N,N-bis(4-iodophenyl)-;F18802;A825662

Chemical Property of Tris(4-iodophenyl)amine

Chemical Property:

• Appearance/Colour: light brown crystalline powder
• Melting Point: 167 °C
• Boiling Point: 559.515 °C at 760 mmHg
• PKA: -5.07±0.50(Predicted)
• Flash Point: 292.185 °C
• PSA: 3.24000
• Density: 2.172 g/cm³
• LogP: 6.97020
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene,dichloromethane
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 622.8104
• Heavy Atom Count: 22
• Complexity: 275

Purity/Quality:

99% ^*data from raw suppliers

Tris(4-iodophenyl)amine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N(C2=CC=C(C=C2)I)C3=CC=C(C=C3)I)I
• Uses: Tris(4-iodophenyl)amine (cas# 4181-20-8) is a useful building block mostly used in the preparation of nanostructures and nanoparticles, such as in the preparation of macrocycle-in-a-macrocycle superstructure with all-gauche conformation by reversible radical association, or in the preparation of supramolecular nanocages on terpyridine building blocks.

Technology Process of Tris(4-iodophenyl)amine

There total 6 articles about Tris(4-iodophenyl)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: 99.0%

N,N-diphenylaminobenzene (603-34-9) → tris(4-iodophenyl)amine (4181-20-8)

Guidance literature:

N,N-diphenylaminobenzene; With trifluorormethanesulfonic acid; [bis(pyridine)iodine]⁺ tetrafluoroborate; In dichloromethane; at 0 - 20 ℃; for 21h;

With water; sodium thiosulfate; In dichloromethane;

Reference yield:

N,N-diphenylaminobenzene (603-34-9) → 4-iodo-N-(4-iodophenyl)-N-phenylbenzenamine (218909-60-5) + tris(4-iodophenyl)amine (4181-20-8)

Guidance literature:

N,N-diphenylaminobenzene; With acetic acid; potassium iodide; at 85 ℃; for 5h; Schlenk technique; Inert atmosphere;

With potassium iodate; at 85 ℃; for 5h; Overall yield = 66 %; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.dyepig.2014.08.016

Reference yield:

diphenylamine (122-39-4) → tris(4-iodophenyl)amine (4181-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere

1.2: 72 h / 140 °C / Inert atmosphere

2.1: mercury(II) oxide / ethanol / 1 h / 20 °C

2.2: 12 h / 20 °C

With potassium tert-butylate; mercury(II) oxide; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

N,N-diphenylaminobenzene

diphenylamine

bromobenzene

Downstream raw materials:

tris(4-diphenylaminophenyl)amine

N,N',N''-tris-[4-(trimethylsilylethynyl)phenyl]phenylamine

tris-4,4',4''-(4-cyanophenylethynyl)triphenylamine

tris[4-(5-phenylthiophen-2-yl)phenyl]amine

Refernces

• 1、 Varnavski, Oleg P.,Ostrowski, Jacek C.,Sukhomlinova, Ludmila,Twieg, Robert J.,Bazan, Guillermo C.,Goodson III, Theodore. "Coherent effects in energy transport in model dendritic structures investigated by ultrafast fluorescence anisotropy spectroscopy". . p. 1736 - 1743. Retrieved 2002.
• 2、 Ni, Jia,Wei, Kai-Ju,Liu, Yangzhong,Huang, Xiao-Chun,Li, Dan. "Silver coordination polymers based on neutral trinitrile ligand: Topology and the role of anion". . p. 3964 - 3976. Retrieved 2010.
• 3、 -. "Flame retardant compound and preparation method and application thereof". Paragraph 0044-0046; 0051-0053; 0056-0058; 0061-0063. . Retrieved 2019/11/12.
• 4、 -. "Synthetic method for tris(4-tetrazolylphenyl)amine". Paragraph 0024. . Retrieved 2018/05/01.