Basic information
- Standard SMILES
CC(=O)c1cccc([N+](=O)[O-])c1- InChIKey
ARKIFHPFTHVKDT-UHFFFAOYSA-N- Molecular formula
- C8H7NO3
- Average molar mass
- 165.15 g/mol
- Monoisotopic mass
- 165.04259308
Overview
3-nitroacetophenone is a light beige powder. (NTP, 1992)
Names & identifiers
- Preferred name
- m-Nitroacetophenone
- IUPAC
- 1-(3-nitrophenyl)ethanone
- English name
- 3-Nitroacetophenone
- Molecular formula
- C8H7NO3
- Molecular weight
- 165.15
Names & synonyms
Show more names
Database identifiers
- CAS
121-89-1- PubChem CID
- 8494
- DTXSID
DTXSID1025722- ChEMBL
CHEMBL1327526- UNII
- SU4B5T763F
- EC Number
- 204-504-3
- Nikkaji
- J33.808G
Properties
Computed structural properties
- XLogP
- 1.4
- 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
- 197
Experimental & physicochemical properties
LogP
log Kow= 1.42 (experimental)
1.42
Solubility
less than 0.1 mg/mL at 68 °F (NTP, 1992)
SOL IN WATER, ETHER
SLIGHTLY SOL IN ALCOHOL
Boiling Point
396 °F at 760 mmHg (NTP, 1992)
202 °C
Melting Point
178 °F (NTP, 1992)
81 °C
Vapor Pressure
0.0024 [mmHg]
3.86X10-5 mm Hg at 25 °C
Physical Description
3-nitroacetophenone is a light beige powder. (NTP, 1992)
Light beige solid; [CAMEO] Tan powder; [MSDSonline]
Physicochemical properties
- Melting point
- 76 · 76-78 °C(lit.)
- Boiling point
- 202 °C · 202 °C(lit.)
- Density
- 1.345 · 1.3450 (rough estimate)
- vapor pressure
- 0.32 Pa · 0.32Pa at 25℃
- refractive index
- 1.5468 · 1.5468 (estimate)
- Flash point
- 202 °C · 202°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- color
- Yellow to yellow-green
- Odor
- Odorless
- Water Solubility
- 0.01 g/100 · <0.01 g/100 mL at 20 ºC
- BRN
- 743002 · 743002
- Stability
- Stable. Incompatible with strong oxidizing agents, strong bases.
- InChI
- 1S/C8H7NO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-5H,1H3
- InChIKey
- ARKIFHPFTHVKDT-UHFFFAOYSA-N
- SMILES
- CC(=O)c1cccc(c1)[N+]([O-])=O
- LogP
- 1.42 · 1.42
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 B5T763F · SU4B5T763F
- NIST Chemistry Reference
- 3 · 3-Nitroacetophenone(121-89-1)
- EPA Substance Registry System
- 3 · 3-Nitroacetophenone (121-89-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xn
- Risk Statements
- 21 · 21
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 2 · 2
- RTECS
- 9625000 · AM9625000
- TSCA
- TSCA listed
- HS Code
- 29147090 · 29147090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 3 · Aquatic Chronic 3
- Hazardous Substances Data
- 121 · 121-89-1(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 27.3% (3 of 11) of reports.
H412 (72.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 11 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Ethanone, 1-(3-nitrophenyl)-
Status: Active Update: 29-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17481
Ethanone, 1-(3-nitrophenyl)-: Does not have an individual approval but may be used under an appropriate group standard
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.
Safety & protection
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.
Disposal Methods
The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon. /Acetophenone/
The following wastewater treatment technologies have been investigated for acetophone: concentration process: resin adsorption. /Acetophenone/
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)
Toxicology
Environmental Fate
TERRESTRIAL FATE: If released to soil, m-nitroacetophenone is not expected to strongly adsorb. Based on an experimental log/octanol water partition coefficient of 1.42(1), a soil adsorption coefficient of 141 can be calculated for m-nitroacetophenone using an appropriate regression equation(2), indicating that m-nitroacetophenone will display high mobility in soil(3). Based on an estimated Henry's Law constant of 9.1X10-8 atm cu-m/mole at 25 °C(4,SRC), m-nitroacetophenone is not expected to volatilize from moist soil to the atmosphere. Its estimated vapor pressure{ 3.86X10-5 mm Hg at 25 °C(5,SRC), indicates that m-nitroacetophenone will not volatilize from dry soil(SRC). Limited data on the laboratory reduction of m-nitroacetophenone using iron porphyrins(6) indicate that it has the potential to biodegrade in soil under anaerobic conditions(6,SRC).
AQUATIC FATE: If released to water, m-nitroacetophenone is not expected to volatilize from water to the atmosphere. Based on an estimated Henry's Law constant of 9.1X10-8 atm cu-m/mole at 25 °C(1,SRC), the estimated half-life for volatilization from a model river 1 m deep flowing at 1 m/sec with a wind speed of 3 m/sec is 517 days(2,SRC). Based on an experimental log/octanol water partition coefficient of 1.42(3), a bioconcentration factor of 7.1 can be calculated for m-nitroacetophenone using an appropriate regression equation(2), indicating that it will not bioconcentrate in fish and aquatic organisms(SRC). An estimated soil adsorption coefficient of 141(2-3,SRC) indicates that it will not adsorb to sediment and suspended organic matter(SRC). Limited data on the laboratory reduction of m-nitroacetophenone using iron porphyrins(4) indicate that it has the potential to biodegrade in water under anaerobic conditions(4,SRC).
ATMOSPHERIC FATE: If released to the atmosphere, m-nitroacetophenone is expected to undergo a slow gas-phase reaction with photochemically produced hydroxyl radicals. An estimated rate constant for this process of 2.94X10-13 cu-cm/molec sec(1,SRC) translates to an atmospheric half-life of 55 days using an average hydroxyl radical concn of 5X10+5 molec/cu-cm(1). The estimated water solubility of m-nitroacetophenone, 750 mg/L at 25 °C(2,SRC), indicates that it may undergo atmospheric removal by wet deposition processes(SRC).
Soil Adsorption/Mobility
Based on an experimental log/octanol water partition coefficient of 1.42(1), a soil adsorption coefficient of 141 can be calculated for m-nitroacetophenone using an appropriate regression equation(2). This value indicates that m-nitroacetophenone will display high mobility in soil(3).
Artificial Pollution Sources
m-Nitroacetophenone is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds(1). It may be released to the environment in wastewater(2) and as a fugitive emission during its production and use(SRC).
Environmental Biodegradation
The nitro group of m-nitroacetophenone was found to undergo reductive transformation in aqueous solutions in the presence of iron porphyrins(1) which indicates that it has the potential to undergo reductive biodegradation in the environment under anaerobic conditions(1,SRC).
Environmental Bioconcentration
Based on an experimental log/octanol water partition coefficient of 1.42(1), a bioconcentration factor of 7.1 can be calculated for m-nitroacetophenone using an appropriate regression equation(2). This value indicates that m-nitroacetophenone will not bioconcentrate in fish and aquatic organisms(SRC).
Volatilization from Water/Soil
Based on an estimated Henry's Law constant of 9.1X10-8 atm cu-m/mole at 25 °C(1,SRC), m-nitroacetophenone is not expected to volatilize from water or moist soil to the atmosphere. The estimated half-life for volatilization from a model river 1 m deep flowing at 1 m/sec with a wind speed of 3 m/sec is 517 days(2,SRC). An estimated vapor pressure for m-nitroacetophenone, 3.86X10-5 mm Hg at 25 °C(3,SRC), indicates that it will not volatilize from dry soil(SRC).
Environmental Abiotic Degradation
An estimated rate constant for the gas-phase reaction of m-nitroacetophenone with photochemically produced hydroxyl radicals of 2.94X10-13 cu-cm/molec sec(1,SRC) translates to an atmospheric half-life of 55 days using an average atmospheric hydroxyl radical concn of 5X10+5 molec/cu-cm(1).
Environmental Fate/Exposure Summary
m-Nitroacetophenone is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds. It may be released to the environment in wastewater and as a fugitive emission during its production and use. If released to soil, m-nitroacetophenone is expected to display high mobility. It not is expected to volatilize from either moist or dry soil to the atmosphere. Limited laboratory data indicate that it has the potential to biodegrade in soil under anaerobic conditions. If released to water, m-nitroacetophenone is not expected to volatilize to the atmosphere. The estimated half-life for volatilization from a model river is 517 days. m-Nitroacetophenone is not expected to bioconcentrate in fish and aquatic organisms nor is it expected to adsorb to sediment and suspended organic matter. Limited laboratory data indicate that it has the potential to biodegrade in water under anaerobic conditions. If released to the atmosphere, m-nitroacetophenone may undergo atmospheric removal by a slow reaction with photochemically produced hydroxyl radicals; the estimated half-life for this process is 55 days. m-Nitroacetophenone may also undergo atmospheric removal by wet deposition processes. Occupational exposure to m-nitroacetophenone may occur by dermal contact during its production, formulation and use. (SRC)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AM9625000
- hs_code
- 29147090
- Toxicity
- mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
- risk_code
- 21
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H332-H335
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3
- Precautionary statements
- P261-P280-P305+P351+P338
- Hazardous Substances Data
- 121-89-1(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used to make dyes and other organic compounds; [HSDB]
m-Nitroacetophenone is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds.
U.S. Imports
(1978) 5.00X10+6 G (PRINCPL CUSTMS DISTS)
(1979) 5.31X10+7 G (PRINCPL CUSTMS DISTS)
U.S. Production
(1977) PROBABLY GREATER THAN 2.27X10+6 G
(1979) PROBABLY GREATER THAN 2.27X10+6 G
Applications
Uses3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.
Uses3′-Nitroacetophenone can undergo high hydrostatic pressure-assisted reduction with Ni–Al alloy in water to form 1-(3-aminophenyl)ethanol.
General Description3-nitroacetophenone is a light beige powder. It is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds. (NTP, 1992)
Preparation methods
Preparation3-Nitroacetophenone is synthesized from acetophenone by nitration.Synthesis of 3-nitroacetophenone
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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