4,4'-Methylenedianiline synthesis
- Product Name:4,4'-Methylenedianiline
- CAS Number:101-77-9
- Molecular formula:C13H14N2
- Molecular Weight:198.26
1817-74-9
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101-77-9
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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
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62-53-3
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6582-52-1
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101-77-9
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50-00-0
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62-53-3
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1208-52-2
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101-77-9
345 suppliers
$15.00/25g
50-00-0
844 suppliers
$10.00/25g
62-53-3
627 suppliers
$10.00/1g
1208-52-2
83 suppliers
$75.00/25mg
6582-52-1
34 suppliers
inquiry
101-77-9
345 suppliers
$15.00/25g