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3'-ニトロアセトフェノン

m-Nitroacetophenone

HCID 8494
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
121-89-1
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

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
名称をさらに表示
3'-ニトロアセトフェノン1-ニトロ-3-アセチルベンゼンメチル3-ニトロフェニルケトンメチル(3-ニトロフェニル)ケトン1-(3-ニトロフェニル)エタノン1-アセチル-3-ニトロベンゼン3-アセチル-1-ニトロベンゼンM-ニトロアセトフェノン3′-ニトロアセトフェノン(m-〃)3′‐ニトロアセトフェノン3-ニトロアセトフェノン3′-ニトロアセトフェノン(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

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補完中

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

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

log Kow= 1.42 (experimental)

1.42

Color/FormNEEDLES FROM ALCOHOL
Solubility · 3 件

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

SOL IN WATER, ETHER

SLIGHTLY SOL IN ALCOHOL

Boiling Point · 2 件

396 °F at 760 mmHg (NTP, 1992)

202 °C

Melting Point · 2 件

178 °F (NTP, 1992)

81 °C

Vapor Pressure · 2 件

0.0024 [mmHg]

3.86X10-5 mm Hg at 25 °C

Physical Description · 2 件

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

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

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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 · 3 件

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 件

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 ReactionsInsoluble in water.
Hazard Classes and Categories

化学と産業

用途と製造

Uses · 2 件

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 件

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

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

U.S. Production · 2 件

(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

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 · 3 件

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.]

関連反応

44 件
反応記録を作成
HRID 45674 の反応式
HRID 45674反応物としてuspto-grants-2013_09
HRID 117416 の反応式
HRID 117416反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 138322 の反応式
HRID 138322反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 209444 の反応式
HRID 209444反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 221399 の反応式
HRID 221399反応物としてuspto-grants-2012_06
HRID 268298 の反応式
HRID 268298反応物としてuspto-grants-1976_03
HRID 281542 の反応式
HRID 281542反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 326612 の反応式
HRID 326612反応物としてuspto-grants-1993_12
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

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.

Aquatic Chronic 3 (72.7%)

安全と保護具

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

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 件

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 件

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 件

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 · 3 件

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 件

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 件

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 件

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 件

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 件

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 件

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 件

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)

上流・下流製品情報

上流原料

2'-ニトロアセトフェノンアセトフェノン3-ニトロフェニルボロン酸3-エチル-1-ニトロベンゼン1-(3-ニトロフェニル)エタノール3-ニトロ-1-エチニルベンゼン1,2-フェニレンジアミンアセトニトリルトリフルオロメタンスルホン酸銀酢酸

下流製品

Ethyl 5-(3-nitrophenyl)-1H-pyrazole-3-carboxylate3'-シアノアセトフェノンAplpha-bromo-m-benzoyloxyacetophenone3-ニトロ-1-エチニルベンゼン5-(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'-アミノアセトフェノン1-Propanone, 3-(dimethylamino)-1-(3-nitrophenyl)-(2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one