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3'-Nitroacetophenon

m-Nitroacetophenone

HCID 8494
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Grundinformationen

CAS
121-89-1
Standard-SMILES
CC(=O)c1cccc([N+](=O)[O-])c1
InChIKey
ARKIFHPFTHVKDT-UHFFFAOYSA-N
Summenformel
C8H7NO3
Durchschnittliche Molmasse
165,15 g/mol
Monoisotopische Masse
165,04259308

Überblick

3-nitroacetophenone is a light beige powder. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
m-Nitroacetophenone
IUPAC
1-(3-nitrophenyl)ethanone
Lokaler Name
3'-Nitroacetophenon
Englischer Name
3-Nitroacetophenone
Summenformel
C8H7NO3
Molmasse
165.15

Namen und Synonyme

3'-Nitroacetophenone121-89-13-Nitroacetophenone1-(3-Nitrophenyl)ethanoneM-NITROACETOPHENONEEthanone, 1-(3-nitrophenyl)-m-AcetylnitrobenzeneMethyl 3-nitrophenyl ketoneAcetophenone, 3'-nitro-USAF MA-13-Nitroacetofenon(3-Nitrophenyl) methyl ketone
Weitere Namen anzeigen
(3-nitrophenyl)methylketoneusafma-1AKOS 233-65AURORA 14018AKOS BBS-00003220
NSC 55111-Acetyl-3-nitrobenzene3-Nitroacetofenon [Czech]CCRIS 2330DTXSID1025722HSDB 2710EINECS 204-504-31-(3-nitrophenyl)-ethanone

Datenbank-Bezeichner

CAS
121-89-1
PubChem CID
8494
DTXSID
DTXSID1025722
ChEMBL
CHEMBL1327526
UNII
SU4B5T763F
EC Number
204-504-3
Nikkaji
J33.808G

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,4
Polarare Oberfläche (TPSA)
62,9 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
12
Formalladung
0
Komplexität
197

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 Einträge

log Kow= 1.42 (experimental)

1.42

Color/FormNEEDLES FROM ALCOHOL
Solubility · 3 Einträge

less than 0.1 mg/mL at 68 °F (NTP, 1992)

SOL IN WATER, ETHER

SLIGHTLY SOL IN ALCOHOL

Boiling Point · 2 Einträge

396 °F at 760 mmHg (NTP, 1992)

202 °C

Melting Point · 2 Einträge

178 °F (NTP, 1992)

81 °C

Vapor Pressure · 2 Einträge

0.0024 [mmHg]

3.86X10-5 mm Hg at 25 °C

Physical Description · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 3 Einträge

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

Fire HazardsFlash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)
Hazards SummaryA mutagen and mild skin irritant; [RTECS] Emergency treatment: Irritants; [HSDB] An irritant; [MSDSonline]
Reactive GroupKetones
Reactivity Profile · 1 Eintrag

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

Chemie und Industrie

Verwendung und Herstellung

Uses · 2 Einträge

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 · 2 Einträge

(1978) 5.00X10+6 G (PRINCPL CUSTMS DISTS)

(1979) 5.31X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 Einträge

(1977) PROBABLY GREATER THAN 2.27X10+6 G

(1979) PROBABLY GREATER THAN 2.27X10+6 G

Methods of ManufacturingNITRATION OF ACETOPHENONE
General Manufacturing InformationEthanone, 1-(3-nitrophenyl)-: ACTIVE

Anwendungen

Verwenden3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.

Darstellung

synthetische3-Nitroacetophenone is synthesized from acetophenone by nitration.Synthesis of 3-nitroacetophenone

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2'-NitroacetophenonAcetophenon3-Nitrophenylboronic acid1-Ethyl-3-nitrobenzolMethyl m-nitrophenyl carbinol

Zugehörige Reaktionen

44
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 45674
HRID 45674als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 117416
HRID 117416als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 138322
HRID 138322als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 209444
HRID 209444als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 221399
HRID 221399als Eduktuspto-grants-2012_06
Reaktionsgleichung von HRID 268298
HRID 268298als Eduktuspto-grants-1976_03
Reaktionsgleichung von HRID 281542
HRID 281542als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 326612
HRID 326612als Eduktuspto-grants-1993_12
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3-nitroacetophenone is a light beige powder. (NTP, 1992)

Light beige solid; [CAMEO] Tan powder; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
76 · 76-78 °C(lit.)
Siedepunkt
202 °C · 202 °C(lit.)
Dichte
1.345 · 1.3450 (rough estimate)
Dampfdruck
0.32 Pa · 0.32Pa at 25℃
Brechungsindex
1.5468 · 1.5468 (estimate)
Flammpunkt
202 °C · 202°C
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Crystalline Powder
Farbe
Yellow to yellow-green
Geruch (Odor)
Odorless
Wasserlöslichkeit
0.01 g/100 · <0.01 g/100 mL at 20 ºC
BRN
743002 · 743002
Stabilität
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
NIST chemische Informationen
3 · 3-Nitroacetophenone(121-89-1)
EPA chemische Informationen
3 · 3-Nitroacetophenone (121-89-1)
Insoluble in water.
Hazard Classes and CategoriesAquatic Chronic 3 (72.7%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this compound can be extinguished using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

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) · 1 Eintrag

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)

Toxikologische Informationen

Environmental Fate · 3 Einträge

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 · 1 Eintrag

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).

Natural Pollution Sourcesm-Nitroacetophenone an anthropogenic compound and it is not known to be produced by natural sources. (SRC)
Artificial Pollution Sources · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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).

Non-Human Toxicity ExcerptsRATED 1 ON RABBIT EYES ON SCALE OF 1 TO 10 ACCORDING TO DEGREE OF INJURY OBSERVED AFTER 24 HR. THE MOST SEVERE INJURIES HAVE BEEN RATED 10.
Environmental Abiotic Degradation · 1 Eintrag

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).

Probable Routes of Human ExposureOccupational exposure to m-nitroacetophenone may occur by dermal contact during its production, formulation or use. (SRC)
Environmental Fate/Exposure Summary · 1 Eintrag

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)

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29147090
RTECS-Nr.
AM9625000
risk_code
21
Toxizität
mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
hazard_code
Xn
safety_code
22-24/25
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
121-89-1(Hazardous Substances Data)
Hazard Classifications
Aquatic Chronic 3
1-Ethinyl-3-nitrobenzol
o-Phenylendiamin
Acetonitril
Silbertrifluormethansulfonat
Essigsure

Nachgelagerte Produkte

Ethyl 5-(3-nitrophenyl)-1H-pyrazole-3-carboxylate3-AcetylbenzonitrilAplpha-bromo-m-benzoyloxyacetophenone1-Ethinyl-3-nitrobenzol5-(3-Nitro-phenyl)-1H-pyrazole-3-carboxylic acid(2E)-1-(3-nitrophenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-oneEthyl 4-(3-nitrophenyl)-2,4-dioxobutanoate3-Aminoacetophenon1-Propanone, 3-(dimethylamino)-1-(3-nitrophenyl)-(2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one