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Nitroapocynin

From Wikipedia, the free encyclopedia
Nitroapocynin
Names
Preferred IUPAC name
1-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethan-1-one
Other names
1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone
4'-Hydroxy-3'-methoxy-5'-nitroacetophenone
Nitroapocynin
5-Nitroapocynin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C9H9NO5/c1-5(11)6-3-7(10(13)14)9(12)8(4-6)15-2/h3-4,12H,1-2H3
    Key: PGKVPHVPNDBJTO-UHFFFAOYSA-N
  • CC(=O)C1=CC(=C(C(=C1)OC)O)[N+](=O)[O-]
Properties
C9H9NO5
Molar mass 211.173 g·mol−1
Appearance Yellow powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nitroapocynin is a mono-nitrated form of apocynin.

Synthesis

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Apocynin can be nitrated with sodium nitrate and acidic ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate in acetonitrile solvent.[1][2]

References

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  1. ^ Tajik, H.; Niknam, K.; Parsa, F. (2009). "Using acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions". Journal of the Iranian Chemical Society. 6: 159–164. doi:10.1007/BF03246515. S2CID 55676239.
  2. ^ Babu, Sainath; Raghavamenon, Achuthan C.; Fronczek, Frank R.; Uppu, Rao M. (2009). "4-Hydroxy-3-methoxy-5-nitroacetophenone (5-nitroapocynin)". Acta Crystallographica Section E. 65 (9): o2292-3. doi:10.1107/S160053680903390X. PMC 2969931. PMID 21577684.