2,4,6-TRI-TERT-BUTYLANILINE Chemical Properties

Melting point:

145-147 °C(lit.)

Boiling point:

302.0±21.0 °C(Predicted)

Density 

0.896±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

3.30±0.10(Predicted)

color 

White to Light yellow

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

2272612

InChI

InChI=1S/C18H31N/c1-16(2,3)12-10-13(17(4,5)6)15(19)14(11-12)18(7,8)9/h10-11H,19H2,1-9H3

InChIKey

REJGDSCBQPJPQT-UHFFFAOYSA-N

SMILES

C1(N)=C(C(C)(C)C)C=C(C(C)(C)C)C=C1C(C)(C)C

CAS DataBase Reference

961-38-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2921490090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,4,6-TRI-TERT-BUTYLANILINE Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

2,4,6-Tri-tert-butylnitrobenzene (bulky amine) is used in the synthesis of monomeric iminophosphorane

Uses

2,4,6-Tri-tert-butylnitrobenzene (bulky amine) was used in the synthesis of monomeric iminophosphorane.

Definition

ChEBI: 2,4,6-tri-tert-butylaniline is an alkylbenzene.

Synthesis

The general procedure for the synthesis of 2,4,6-tri-tert-butylaniline from 2,4,6-tri-tert-butylnitrobenzene was as follows: in a 4 mL glass reaction flask equipped with a septum cap and a magnetic stirring bar, Co-Co3O4Chit-700 catalyst (10 mg, 3.4 mol/kg Co), nitroaromatic hydrocarbons (0.5 mmol, 1.0 equiv), triethylamine ( 35 μL, 0.25 mmol, 0.5 equiv), and EtOH/H2O (3:1, 2 mL) mixed solvent. The reaction vial was placed in a 300 mL autoclave and pressurized to 40 bar after five displacements with hydrogen. The reaction mixture was stirred at 110 °C until the reaction was complete. At the end of the reaction, it was cooled to room temperature and the pressure in the autoclave was slowly released. The crude reaction mixture was filtered through a cotton fitted pipette and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate), and pure 2,4,6-tri-tert-butylaniline derivatives were obtained after removing the solvent under reduced pressure. Using the catalyst of the present invention, efficient preparation of the target aniline derivatives from the corresponding nitroaromatics can be realized.

References

[1] ChemSusChem, 2017, vol. 10, # 15, p. 3035 - 3039
[2] Patent: WO2018/114777, 2018, A1. Location in patent: Page/Page column 31-32
[3] Journal of the American Chemical Society, 1991, vol. 113, # 22, p. 8437 - 8443
[4] Journal of the American Chemical Society, 1982, vol. 104, # 25, p. 7191 - 7195
[5] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14738 - 14742

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