Tris(4-iodophenyl)amine Chemical Properties

Melting point:

167 °C

Boiling point:

559.5±45.0 °C(Predicted)

Density 

2.172±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Toluene,dichloromethane

pka

-5.07±0.50(Predicted)

form 

Liquid

color 

Clear colorless

CAS DataBase Reference

4181-20-8(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

HS Code 

29214990

Tris(4-iodophenyl)amine Usage And Synthesis

Chemical Properties

Light brown crystalline powder

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.

Synthesis

The general procedure for the synthesis of tris(4-iodophenyl)amine was as follows: first, IPe2BF4 (5.3 g, 14.3 mmol) and triphenylamine (1 g, 4.1 mmol) were mixed in CH2Cl2 (60 mL) and cooled to 0 °C under nitrogen protection. Subsequently, trifluoromethanesulfonic acid (TfOH: 900 μL, 4.1 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature under nitrogen atmosphere for 21 h until a reddish brown solution was formed. After completion of the reaction, saturated aqueous NaHCO3 and Na2S2O3 were added to the mixture and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed sequentially with saturated NaHCO3 and NaCl solutions and then dried with Na2SO4. The dried organic phase was filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane/EtOAc = 5/1) to afford tris(4-iodophenyl)amine (2.507 g, 99% yield). The product was characterized by 1H NMR and 13C NMR: 1H NMR (CDCl3) δ 7.54 (d, J = 8.9 Hz, 6H), 6.81 (d, J = 8.9 Hz, 6H); 13C NMR (CDCl3) δ 146.5, 138.4, 126.0. The NMR data confirm that the resulting compound is tris(4-iodophenyl)amine.

References

[1] Patent: US2008/227939, 2008, A1. Location in patent: Page/Page column 17
[2] Patent: US2009/54649, 2009, A1. Location in patent: Page/Page column 43-44
[3] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6287 - 6290
[4] European Journal of Organic Chemistry, 2013, # 13, p. 2608 - 2620
[5] Tetrahedron, 2014, vol. 70, # 15, p. 2546 - 2555

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