ChemicalBook CAS DataBase List 2,4,6-Trimethylaniline

2,4,6-Trimethylaniline synthesis

11synthesis methods

Product Name:2,4,6-Trimethylaniline
CAS Number:88-05-1
Molecular formula:C9H13N
Molecular Weight:135.21

2,4,6-Trimethylaniline is prepared by selective mononitration of mesitylene, avoiding oxidation of the methyl groups.
Mix sulfuric acid and nitric acid into mixed acid, nitrify with mesitylene at atmospheric pressure below 10°C for 4 hours, stand for stratification, and let off the waste acid. The obtained 2,4,6-trimethylnitrobenzene, iron powder, hydrochloric acid and water were prepared in a ratio of 1:3.74:0.9:2.22 (mol ratio) for reduction reaction at 100-105°C for 8h. Crude 2,4,6-Trimethylaniline was then distilled off from the reduced material and purified by distillation.

36016-39-4 Synthesis

tert-Butyl (Mesitylsulfonyl)oxycarbaMate

36016-39-4
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$19.00/250mg

108-67-8 Synthesis

108-67-8
376 suppliers
$5.00/5G

88-05-1
319 suppliers
$6.00/1g

Yield:88-05-1 70%

Reaction Conditions:

with Rh₂(esp)2;trifluoroacetic acid in 2,2,2-trifluoroethanol at 0 - 20; for 25 h;Inert atmosphere;

Steps:

4 FIG. 2: Entry 4 (In Situ Generation Procedure)

To a 0° C. solution of 6 mesitylene (7a: 42 μL, 0.3 mmol) and 54 tert-butyl (mesitylsulfonyl)oxycarbamate (4d: 142 mg, 0.45 mmol, 1.5 equiv) in TFE (3 mL) was added 8 CF₃CO₂H (TFA: 46 μL, 0.6 mmol, 2 equiv) and 26 Rh₂(esp)₂(4.55 mg, 6 μmol). The reaction was allowed to gradually warm to rt overnight. After 25 h, the reaction mixture (a suspension) was poured carefully into sat. aq. NaHCO₃(15 mL) and extracted with EtOAc (3×7 mL). The combined organic extracts were dried over Na₂SO₄, filtered, and concentrated in vacuo. The residue was purified by PTLC (15% EtOAc/hexanes) to give 52 2,4,6-trimethylaniline (8c: 28.5 mg, 70%) as an oil whose spectral characteristics were concordant with literature values (see above).

References:

US2019/152892,2019,A1 Location in patent:Paragraph 0132; 0148; 0149

5980-97-2 Synthesis