p-Nitroacetophenone
Basic information
- CAS
100-19-6- Standard SMILES
CC(=O)c1ccc([N+](=O)[O-])cc1- InChIKey
YQYGPGKTNQNXMH-UHFFFAOYSA-N- Molecular formula
- C8H7NO3
- Average molar mass
- 165.15 g/mol
- Monoisotopic mass
- 165.04259309
Overview
P-nitroacetophenone appears as yellow prisms or bright yellow powder. (NTP, 1992)
Names & identifiers
- Preferred name
- p-Nitroacetophenone
- IUPAC
- 1-(4-nitrophenyl)ethanone
- English name
- 4-Nitroacetophenone
- Molecular formula
- C8H7NO3
- Molecular weight
- 165.15
Names & synonyms
4'-Nitroacetophenone100-19-6p-Nitroacetophenone1-(4-Nitrophenyl)ethanone4-NITROACETOPHENONEp-AcetylnitrobenzeneEthanone, 1-(4-nitrophenyl)-p-Nitrophenyl methyl ketoneParanitroacetophenonePNAPAcetophenone, 4'-nitro-Methyl-p-nitrophenyl ketone
Show more names
1-(4-NITROPHENYL)ETHAN-1-ONENitroacetophenoneNSC 41590Bromo-2’AURORA KA-7140AKOS BBS-00003219p-Nitroacetophenon
4-Acetylnitrobenzene1-Acetyl-4-nitrobenzeneDTXSID10257244-nitrophenyl methyl ketoneMethyl 4-nitrophenyl ketone4FM2J8HQ27NSC-41590DTXCID105724
Database identifiers
- CAS
100-19-6- PubChem CID
- 7487
- DTXSID
DTXSID1025724- ChEMBL
CHEMBL167997- ChEBI
CHEBI:28735- UNII
- 4FM2J8HQ27
- EC Number
- 202-827-4
- Nikkaji
- J803F
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 62.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 189
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesChemical shift
LogP1.61
Boiling Point396 °F at 760 mmHg (NTP, 1992)
Melting Point176 to 180 °F (NTP, 1992)
Vapor Pressure0.0024 [mmHg]
Physical Description
P-nitroacetophenone appears as yellow prisms or bright yellow powder. (NTP, 1992)
Yellow solid; [CAMEO] Yellow chips or crystals; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 75 · 75-78 °C(lit.)
- Boiling point
- 202 °C · 202 °C(lit.)
- Density
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information4'-Nitroacetophenone: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards SummaryAn irritant; Harmful by ingestion; [Alfa Aesar MSDS] See Acetophenone (causes acute solvent syndrome) and Nitrobenzene (causes primary methemoglobinemia).
Reactive GroupKetones
Reactivity Profile
A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
Applications
Uses4''-Nitroacetophenone is used as a reagent in the synthesis of 4-Nitroacetophenone thiosemicarbazone derivatives and their copper(II) complexes which have potential anti-trypanosomal activity in vitro. Also used as a reagent in the synthesis of (R)-(4-Nitrophenyl)oxirane (N504430) and (S)-(4-Nitrophenyl)oxirane (N504435).
General DescriptionP-nitroacetophenone appears as yellow prisms or bright yellow powder. (NTP, 1992)
Preparation methods
PreparationIn the presence of catalyst cobalt stearate, p-nitroethylbenzene is oxidized to synthesize 4-nitroacetophenone with air at 140-150°C and 0.2MPa pressure. The reaction product is washed with water, neutralized, centrifugally dehydrated, and dried to obtain a finished product.
Upstream & downstream products
Upstream raw materials
Related reactions
88 records
Compound notes
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