4,4'-DI-TERT-BUTYLDIPHENYLAMINE Chemical Properties

Melting point:

108 °C

Boiling point:

195 °C / 3mmHg

Density 

0.974±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

1.47±0.40(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C20H27N/c1-19(2,3)15-7-11-17(12-8-15)21-18-13-9-16(10-14-18)20(4,5)6/h7-14,21H,1-6H3

InChIKey

OPEKHRGERHDLRK-UHFFFAOYSA-N

SMILES

C1(NC2=CC=C(C(C)(C)C)C=C2)=CC=C(C(C)(C)C)C=C1

Safety Information

HS Code 

29214990

4,4'-DI-TERT-BUTYLDIPHENYLAMINE Usage And Synthesis

Chemical Properties

White needle-like crystals

Uses

Bis(4-tert-butylphenyl)amine could be a useful reagent for synthesizing efficient luminogens with AIE features that permit imaging the brain through an intact skull.

Synthesis

Bis(dibenzylideneacetone)palladium (1.7 g, 3 mmol) and tri-tert-butylphosphine (1.2 g, 6 mmol) were added to toluene (200 mL) under argon protection using 4-tert-butylaniline (14.9 g, 100 mmol) and 4-tert-butylbromobenzene (21.2 g, 100 mmol). The mixture was heated to 90 °C, followed by the addition of sodium tert-butoxide (0.6 g, 6 mmol) and continued heating to 110 °C. The reaction was carried out under an argon atmosphere. The reaction mixture was stirred under argon atmosphere for 12 hours. After completion of the reaction, it was cooled to room temperature and separated by addition of water. The organic layer was concentrated to give a solid product which was purified by silica gel column chromatography to give the target product di(4-tert-butylphenyl)amine (20.2 g, 72 mmol) in 72% yield.

References

[1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 4, p. 1021 - 1027
[2] Patent: CN107286027, 2017, A. Location in patent: Paragraph 0052; 0064; 0065; 0066
[3] Patent: CN107573306, 2018, A. Location in patent: Paragraph 0030; 0038
[4] Patent: CN107573357, 2018, A. Location in patent: Paragraph 0039; 0040
[5] Tetrahedron Letters, 2001, vol. 42, # 27, p. 4421 - 4424

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