ChemicalBook CAS DataBase List 4,4'-Methylenedianiline

4,4'-Methylenedianiline synthesis

12synthesis methods

Product Name:4,4'-Methylenedianiline
CAS Number:101-77-9
Molecular formula:C13H14N2
Molecular Weight:198.26

1817-74-9
62 suppliers
$60.00/1g

101-77-9
361 suppliers
$15.00/25g

Yield:101-77-9 93%

Reaction Conditions:

with hydrazine in methanol at 50;

Steps:

2

General procedure: The commercially available or synthesized dinitro compounds (1 mmol) were dissolved in methanol and 4 equivalents of hydrazine were added followed by a pinch of Raney nickel and the mixture was heated to 50 C. A vigorous evolution of hydrogen gas ensued and the solution slowly turned colourless in 2e3 h time. It was cooled and passed through a pad of celite and washed with ethyl acetate, dried and concentrated to obtain the diamine which was subsequently washed with hexane to obtain sufficiently pure compounds to use directly in the next step as judged from 1H NMR. 4.4.2
4,4'-Methylenedianiline (8b)
Yield: 93%; mp 97-99 °C; ¹H NMR (DMSO-d₆), δ (ppm): 3.54 (br s, 4H), 3.79 (s, 2H), 6.61 (d, J = 8.2 Hz, 4H), 6.99 (d, J = 8.2 Hz, 4H); ¹³C NMR (DMSO-d₆), δ (ppm): 40.0, 115.1, 129.4, 131.7, 144.1; ESI-MS: Calc. for C₁₃H₁₄N₂: 198.1, found 199.2 (M + H⁺).

References:

Banerjee, Moloy;Farahat, Abdelbasset A.;Kumar, Arvind;Wenzler, Tanja;Brun, Reto;Munde, Manoj M.;Wilson, W. David;Zhu, Xiaohua;Werbovetz, Karl A.;Boykin, David W. [European Journal of Medicinal Chemistry,2012,vol. 55,p. 449 - 454]

50-00-0 Synthesis