(2E)-3-(3-nitrophenyl)-1-phenylprop-2-en-1-one

• ChemBase ID: 301883
• Molecular Formular: C15H11NO3
• Molecular Mass: 253.25274
• Monoisotopic Mass: 253.07389322
• SMILES: c1ccc(cc1)C(=O)/C=C/c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: O=C(c1ccccc1)/C=C/c1cccc(c1)[N+](=O)[O-]
• InChI: InChI=1S/C15H11NO3/c17-15(13-6-2-1-3-7-13)10-9-12-5-4-8-14(11-12)16(18)19/h1-11H/b10-9+
• InChIKey: SMFBODMWKWBFOK-MDZDMXLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(3-nitrophenyl)-1-phenylprop-2-en-1-one
• IUPAC Traditional name: chalcone, 3-nitro-
• Synonyms: 2-(3-Nitrobenzylidene)acetophenone; 3-Nitrochalcone; 3-硝基查耳酮

Database IDs

• CAS Number: 614-48-2
• EC Number: 210-384-3
• MDL Number: MFCD00024571
• Beilstein Number: 1464265

CALCULATED PROPERTIES

• Acid pKa: 16.366968
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.8303094
• LogD (pH = 7.4): 3.8303094
• Log P: 3.8303094
• Molar Refractivity: 73.1975 cm^3
• Polarizability: 27.182686 Å^3
• Polar Surface Area: 60.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 145-146°C

Safety Information

• RTECS: FL7075490
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98+%

REFERENCES

• Thiophenols, in the presence of piperidine, form S-1-(3-nitrophenyl)-2-benzoylethyl thioethers, which have been used as a means of protection during electrophilic aromatic substitution reactions. The protecting group was removed by treatment with Pb(OAc)₂: J. Am. Chem. Soc., 75, 4357 (1953).