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4'-Nitroacetophenon
1-(4-NITROPHENYL)ETHAN-1-ONE · Nitroacetophenone · PNAP · 1-(4-nitrophenyl)ethanone · P-NITROACETOPHENONE · NSC 41590 · Bromo-2’AURORA KA-7140 · AKOS BBS-00003219
Identifikatoren & physikalische Daten
| CAS No. | 100-19-6 |
|---|---|
| Summenformel | C8H7NO3 |
| Durchschnittliche Molmasse | 165,15 g/mol |
| Monoisotopische Masse | 165,04259309 g/mol |
| SMILES | CC(=O)c1ccc([N+](=O)[O-])cc1 |
| InChIKey | YQYGPGKTNQNXMH-UHFFFAOYSA-N |
| PubChem CID | 7487 |
| ChEMBL | CHEMBL167997 |
| ChEBI | CHEBI:28735 |
| EC No. | 202-827-4 |
| DTXSID | DTXSID1025724 |
| Lokaler Name | 4'-Nitroacetophenon |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 62,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 189 |
| Siedepunkt | 396 °F at 760 mmHg (NTP, 1992)202 °C(lit.) |
| Schmelzpunkt | 176 to 180 °F (NTP, 1992)75-78 °C(lit.) |
| Dampfdruck | 0.0024 [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] |
| Dichte | 1.3450 (rough estimate) |
| Brechungsindex | 1.5468 (estimate) |
| Flammpunkt | 201-202°C |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| Farbe | Yellow |
| Löslichkeit | Insoluble in water. |
| BRN | 607777 |
| InChI | InChI=1S/C8H7NO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5H,1H3 |
| InChIKey | YQYGPGKTNQNXMH-UHFFFAOYSA-N |
| SMILES | C(=O)(C1=CC=C([N+]([O-])=O)C=C1)C |
| CAS Datenbank | 100-19-6(CAS DataBase Reference) |
| NIST chemische Informationen | Acetophenone, 4'-nitro-(100-19-6) |
| EPA chemische Informationen | 4-Nitroacetophenone (100-19-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (12.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]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.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | 4'-Nitroacetophenone: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination. (ERG, 2024) |
| Gefahrenübersicht | An irritantHarmful by ingestion[Alfa Aesar MSDS] See Acetophenone (causes acute solvent syndrome) and Nitrobenzene (causes primary methemoglobinemia). |
| Reaktive Gruppe | KetonesNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| 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. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Skin Irrit. 2 (12.5%)Eye Irrit. 2 (25%)STOT SE 3 (12.5%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992) |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29147090 |
| RTECS-Nr. | AM9627000 |
| R-Sätze (R) | 36-22 |
| Gefahrensymbole | Xn |
| hazard_note | Harmful |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
4''-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).
Herstellung & Synthese
synthetische
In 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.