1-(4-Hydroxy-3-nitrophenyl)propan-1-one
Basic information
- CAS
50916-44-4- Standard SMILES
CCC(=O)c1ccc(O)c([N+](=O)[O-])c1- InChIKey
ZXXQSUUUGORSCV-UHFFFAOYSA-N- Molecular formula
- C9H9NO4
- Average molar mass
- 195.17 g/mol
- Monoisotopic mass
- 195.05315777
Names & identifiers
- Preferred name
- 1-(4-Hydroxy-3-nitrophenyl)propan-1-one
- IUPAC
- 1-(4-hydroxy-3-nitrophenyl)propan-1-one
- English name
- 3-nitro-4-hydroxypropiophenone
- Molecular formula
- C9H9NO4
- Molecular weight
- 195.17
Names & synonyms
1-(4-hydroxy-3-nitrophenyl)propan-1-one50916-44-43-nitro-4-hydroxypropiophenoneNSC139710SCHEMBL21775014DTXSID70300887AKOS005145081NSC-1397104'-Hydroxy-3'-nitropropiophenone1-Propanone, 1-(4-hydroxy-3-nitrophenyl)-
Database identifiers
- CAS
50916-44-4- PubChem CID
- 284097
- DTXSID
DTXSID70300887- Nikkaji
- J767.307H
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 83.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 235
Physicochemical properties
- Melting point
- 65.4 · 65.4–66.2°C
- Boiling point
- 296.8 · 296.8±20.0 °C(Predicted)
- Density
- 1.321 · 1.321±0.06 g/cm3(Predicted)
- pka
- 5.33 · 5.33±0.35(Predicted)
Chemistry & industry
Preparation methods
PreparationPreparation by treatment of 4-hydroxypropiophenone with fuming nitric acid or with nitric acid in concentrated sulfuric acid between 2° and 0° (80%) Preparation by Friedel–Crafts acylation of o-nitrophenol with propionyl chloride in nitrobenzene in the presence of aluminium chloride at 55–60° for 2.5 h, then at r.t. overnight Also obtained (poor yield) by Fries rearrangement of 2-nitrophenyl propionate in nitrobenzene with aluminium chloride at 90° for 8 h, then at r.t. overnight Also obtained by reaction of concentrated nitric acid with 2,2′-dihydroxy-5, 5′-dipropionyldiphenyl sulfide (m.p. 103°) in concentrated sulfuric acid at r.t. overnight.
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Compound notes
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