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Nitroacetonitrile
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Substance index - selected nitrocompounds tested by our group /
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CAS: 13218-13-8
MW: 86.0501
Brutto formula: C2H2N2O2
B.p. [oC]: 55/2mmHg [Ref.]
Density [g/cm3]: 1.36 (18oC) [Ref.]
UV/VIS [nm]: 288 [Ref.]
IR [cm-1]: 2963, 3015, 2363, 1573, 1363 [Ref.]
1H-NMR [ppm]: 5.23 (s, 2H) [Ref.]
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Preparation [Ref.]:
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In 760 mL, four-neck glass equipped with mechanic stirrer, dropping funnel, thermometer and reflux condenser, 60 g of methazonic acid was dissolved in 300 mL of diethyl ether. Next, reaction mixture was heated to boiling, and dropped slowly 43 mL of tionyl chloride. During introduction of tionyl chloride to reaction system, temperature should be higher than 30°C. Solution was stirred for 120 min, filtered and evaporated in argon atmosphere. Oil residue was treatment by 240 mL of diethyl ether and 90 mL of water. Organic layer was separated, dried over anhydrous calcium chloride and evaporated in argon atmosphere. Oil residue was purified by column chromatography. Silica gel was used as stationary phase, and benzene as eluent. 14 g (28%) of pure nitroacetonitrile was obtained as yellow liquid. Product was converted immediately in reaction with aldehydes without storage, as its long-term storage leads to the formation of explosive substances.
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Applications:
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Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes
Boguszewska-Czubara A, Łapczuk-Krygier A., Rykała K., Biernasiuk A., Wnorowski A, Popiołek Ł., Maziarka A., Hordyjewska A., Jasiński R.
Journal of Enzyme Inhibition and Medicinal Chemistry, [in press] DOI: 10.3109/14756366.2015.1070264 |
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In the search for experimental and quantumchemical evidence for zwitterionic nature of (2E)-3-[4-(dimethylamino)phenyl]-2-nitroprop-2-enenitrile - an extreme example of donor-p-acceptor push-pull molecule
Jasiński R., Mirosław B., Demchuk O.M., Babyuk D., Łapczuk-Krygier A.
Journal of Molecular Structure, 1108, 689-697 (2016) |
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In the search for experimental and quantumchemical evidence for zwitterionic nature of (2E)-3-[4-(dimethylamino)phenyl]-2-nitroprop-2-enenitrile - an extreme example of donor-p-acceptor push-pull molecule
Jasiński R., Mirosław B., Demchuk O.M., Babyuk D., Łapczuk-Krygier A.
Journal of Molecular Structure, 1108, 689-697 (2016) |
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Similar compounds: methazonic acid, (E)-2-phenyl-1-cyano-1-nitroethene
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