ChemicalBook CAS DataBase List 4,4'-Ethylenedianiline

4,4'-Ethylenedianiline synthesis

12synthesis methods

Product Name:4,4'-Ethylenedianiline
CAS Number:621-95-4
Molecular formula:C14H16N2
Molecular Weight:212.29

621-96-5
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621-95-4
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Yield:621-95-4 99%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol; for 5 h;

Steps:

f f) Preparation of EDDA from DAS.

DAS (0.1 g, 0.48 mmol) and 10% Pd/C (0.22 g) was mixed with methanol (5 ml) in a two neck round bottom flask and H₂ gas was bubbled into the mixture while stirring. After 5 h the reaction mixture turned pink from orange. The reaction mixture was filtered and solvent was evaporated to get shiny pinkish crude product in 99% yield which was recrystallized using ethanol to get pink colored crystal. The specifications were as follow: ¹H NMR (400 MHz, DMSO-d₆, δ, ppm): 2.61 (s, 4H), 4.79 (s, 2H), 6.49 (d, 2H, J = 8 Hz), 6.85 (d, 2H). ¹³C NMR (100 MHz, DMSO-d₆, δ, ppm): 37.1, 113.9, 128.7, 129.0, 146.3. Mass: m/z = 213.14217 (experimental), 212.1313 (calculated). Melting point: 137 °C.

References:

Kumar, Amit;Tateyama, Seiji;Yasaki, Katsuaki;Ali, Mohammad Asif;Takaya, Naoki;Singh, Rajeev;Kaneko, Tatsuo [Polymer,2016,vol. 83,p. 182 - 189]