p-Nitroacetophenone

HCID 7487CAS 100-19-6

Basic information

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

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

Experimental & physicochemical properties

Boiling Point396 °F at 760 mmHg (NTP, 1992)
Melting Point176 to 180 °F (NTP, 1992)
Vapor Pressure0.0024 [mmHg]
Physical Description · 2 items

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
1.345 · 1.3450 (rough estimate)
refractive index
1.5468 · 1.5468 (estimate)
Flash point
201 · 201-202°C
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (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 exposure; Respiratory 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.

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 Hazards · 1 item

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;TOXIC and/or CORROSIVE; inhalation, 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)

Hazards SummaryAn irritant; Harmful by ingestion; [Alfa Aesar MSDS] See Acetophenone (causes acute solvent syndrome) and Nitrobenzene (causes primary methemoglobinemia).
Reactive GroupKetones;Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 area; take 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 used; if 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)

Nonfire Spill Response · 1 item

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 · 1 item

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 directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Personal Protective Equipment (PPE) · 1 item

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)

Regulatory information

Regulatory Information4'-Nitroacetophenone: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
AM9627000
hs_code
29147090
risk_code
36-22
Signal word
Warning

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
Applications · 2 items

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 · 1 item

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
艾斯提克(山东)生物医药有限公司21-58999881 15623240527 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
聊城作之杭化工有限公司19163518031; 19163518031

Additional notes

DefinitionChEBI: 4-nitroacetophenone is a member of the class of acetophenones that is acetophenone substituted at the para-position by a nitro group. It is a C-nitro compound and a member of acetophenones.

Related reactions

88 records

Linked notes

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