基本情報
- 標準SMILES
CC(=O)c1cccc([N+](=O)[O-])c1- InChIKey
ARKIFHPFTHVKDT-UHFFFAOYSA-N- 分子式
- C8H7NO3
- 平均分子量
- 165.15 g/mol
- 単同位体質量
- 165.04259308
概要
3-nitroacetophenone is a light beige powder. (NTP, 1992)
名称と識別子
- 優先名称
- m-Nitroacetophenone
- IUPAC
- 1-(3-nitrophenyl)ethanone
- 現地名
- 3'-ニトロアセトフェノン
- 英語名
- 3-Nitroacetophenone
- 分子式
- C8H7NO3
- 分子量
- 165.15
名称と別名
名称をさらに表示
データベース識別子
- CAS
121-89-1- PubChem CID
- 8494
- DTXSID
DTXSID1025722- ChEMBL
CHEMBL1327526- UNII
- SU4B5T763F
- EC Number
- 204-504-3
- Nikkaji
- J33.808G
物性
構造計算による物性
- XLogP
- 1.4
- 極性表面積
- 62.9 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 1
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 197
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 76 · 76-78 °C(lit.)
- 沸点
- 202 °C · 202 °C(lit.)
- 比重(密度)
- 1.345 · 1.3450 (rough estimate)
- 蒸気圧
- 0.32 Pa · 0.32Pa at 25℃
- 屈折率
- 1.5468 · 1.5468 (estimate)
- 闪点
- 202 °C · 202°C
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- DMSO(微量)、メタノール(微量)
- 外見
- 結晶性粉末
- 色
- 黄色から黄緑色
- 臭い (Odor)
- 無臭
- 水溶解度
- 0.01 g/100 · <0.01 g/100 mL で 20 ºC
- BRN
- 743002 · 743002
- 安定性
- 安定。強酸化剤、強塩基とは相容れない。
- 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の化学物質情報
- 3 · 3-Nitroacetophenone(121-89-1)
- EPAの化学物質情報
- 3 · 3-Nitroacetophenone (121-89-1)
化学的性質
化学的特性white to light beige crystalline powder or yellow needle-like crystals. soluble in hot water and ether, slightly soluble in ethanol. can be volatile with water vapor.
安全と法規制
GHS分類
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.
危険有害性情報
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.
安全と保護具
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)
毒性情報
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)
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AM9625000
- 毒性
- mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
- hs_code
- 29147090
- risk_code
- 21
- 化審法
- (3)-1243
- hazard_code
- Xn
- safety_code
- 22-24/25
- Hazard Classifications
- Aquatic Chronic 3
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 121-89-1(Hazardous Substances Data)
化学と産業
用途と製造
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
応用分野
使用3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.
一般的な説明3-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)
調製方法
製造方法3-Nitroacetophenone is synthesized from acetophenone by nitration.Synthesis of 3-nitroacetophenone
Acetophenone is carefully dissolved in concentrated sulfuric acid at 0 ℃, and mixed acid is added slowly below 0 ℃. The crude product is precipitated by quenching into ice, filtered, and washed acid free. Purification, mainly from the ortho isomer, is achieved by recrystallization from ethanol with significant lowering of the overall yield to ca. 55 %.
純化方法Distil the ketone in steam and crystallise it from EtOH. [Beilstein 7 IV 656.]
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