Nitroapocynin

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
CAS Number	20716-41-0;
3D model (JSmol)	Interactive image;
ChemSpider	260051;
PubChem CID	294764;
CompTox Dashboard (EPA)	DTXSID00303967 ;
	InChI 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;
	SMILES CC(=O)C1=CC(=C(C(=C1)OC)O)[N+](=O)[O-];
Properties
Chemical formula	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).
	Infobox references

Nitroapocynin is a mono-nitrated form of apocynin.

Synthesis[]

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

^ 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.
^ 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.