ChemicalBook CAS DataBase List BIS(2-NITROPHENYL)DISELENIDE

BIS(2-NITROPHENYL)DISELENIDE synthesis

11synthesis methods

Product Name:BIS(2-NITROPHENYL)DISELENIDE
CAS Number:35350-43-7
Molecular formula:C12H8N2O4Se2
Molecular Weight:402.12

88-74-4 Synthesis

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35350-43-7
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Yield:35350-43-7 88%

Reaction Conditions:

Stage #1: 2-nitro-anilinewith boron trifluoride diethyl etherate in dichloromethane at -15; for 0.25 h;
Stage #2: with n-Butyl nitrite in dichloromethane at -15 - 0; for 1 h;Further stages;

Steps:

4 2.1.4.Synthesisofbis(o-nitrophenyl)diselenide

The proceduresofCasaretal.werefollowed [33]. o-Nitroaniline(17mmol)wasdissolvedindrydichloromethane(25mL)at -15 °C. Borontrufluoride diethyletherate(3.5mL)wasaddeddropwiseandthemixturestirredfor15min.Asolutionofbutylnitrite (22.5mmol)indrydichloromethane(10mL)wasthenad-ded dropwiseandthemixturestirred30minat -15 °C, andanadditional 30minat0 °C. Coldpentane(20mL)wasaddedandthesolution filtered.Theprecipitatewaswashedwithcoldether(200mL).Thecollectedsolidwasthendissolvedinwater(80mL)on icebathandasolutionofKSeCN(17mmol)inwater(20mL)wasaddedover10min.AftercompleteadditionoftheKSeCNsolution, themixturewasstirredforanadditional10min.Theprecipitatewasthen filteredandcollected.Thesolidwasre-dis-solvedinethanol(60mL)andsodiummetal(17mmol)wasaddedportionwise.Themixturewasallowedtostirfor2hatwhichtimethe precipitatewas filtered,washedwithethanol(120mL),andallowedtodryovernighttogive bis(o-nitrophenyl)diselenide(o-NPdS, 3.0g,88%yield): 1H NMR(CDCl3) δ 8.39 (d,2H),7.92(d,2H),7.54-7.42(m,4H); 77Se-NMR (CDCl3, relativetomethylselenide) δ484.37, 77Se NMR(DMSO-d6, relativetomethylselenide) δ 478.76.

References:

Bianco, Christopher L.;Moore, Cathy D.;Fukuto, Jon M.;Toscano, John P. [Free Radical Biology and Medicine,2016,vol. 99,p. 71 - 78]