对乙氧基-N-乙酰乙酰苯胺 | 122-82-7

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 对乙氧基-N-乙酰乙酰苯胺
• 中文别名: 对乙氧基乙酰乙酰苯胺；乙酰基乙酰对乙氧基苯胺；对乙酰基乙酰氨基苯乙醚；N-乙酰乙酰基对氨基苯乙醚；乙酰乙酰对乙氧基苯胺；4-乙氧基乙酰乙酰苯胺；N-乙酰乙酰对乙氧基苯胺；4'-乙氧基乙酰乙酰苯胺；N-乙酰乙酰基-4-乙氧基苯胺；AAPP
• 英文名称: 3-oxo-N-(4'-ethoxyphenyl)butanamide
• 英文别名: N-(4-ethoxyphenyl)-3-oxobutanamide；N-Acetoacetyl-p-ethoxy-anilin；1-aceto-acetyl-amino-4-ethoxy-benzene
• CAS: 122-82-7
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD00043937
• 分子量: 221.256
• InChiKey: WWROGCAUSKGAMX-UHFFFAOYSA-N

物化性质

• 熔点：
  104 °C
• 沸点：
  362.31°C (rough estimate)
• 密度：
  1.2200
• 蒸气密度：
  7.63
• 闪点：
  163 °C
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1(b)
• 危险品运输编号：
  2811
• RTECS号：
  AK5800000
• 海关编码：
  2924299090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险性描述：
  H301
• 储存条件：
  库房应保持通风、低温和干燥的环境。

SDS

p-Acetoacetophenetidide Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: p-Acetoacetophenetidide

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 3
Acute toxicity (Oral)
ENVIRONMENTAL HAZARDS Not classified
GHS label elements
Pictograms or hazard symbols
Signal word Danger
Hazard statement Toxic if swallowed
Precautionary statements
[Prevention] Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
[Response] IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse
mouth.
[Storage] Store locked up.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): p-Acetoacetophenetidide
Percent: >98.0%(GC)(T)
CAS Number: 122-82-7
Synonyms: N-Acetoacetyl-p-phenetidine , N-Acetoacetyl-4-ethoxyaniline , 4'-
Ethoxyacetoacetanilide
Chemical Formula: C12H15NO3

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
p-Acetoacetophenetidide

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Section 4. FIRST AID MEASURES
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Immediately call a POISON CENTER or doctor/physician. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form: crystal - powder
Color: White - Very pale yellow
Odor: No data available
p-Acetoacetophenetidide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:104 °C
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
No data available
Lower:
Upper: No data available
2.7Pa/20°C
Vapor Pressure:
Vapor Density: 7.63
No data available
Density:
Solubility: Soluble in : Methanol

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
Products:

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Section 11. TOXICOLOGICAL INFORMATION
orl-rat LD50:176 mg/kg
Acute Toxicity:
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:
RTECS Number: AK5800000

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: 6.1: Toxic substance.
UN-No: 2811
Proper shipping name: Toxic solid, organic, n.o.s.
Packing group: III
p-Acetoacetophenetidide

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
白色片状结晶粉末

用途
用于合成C.I.颜料黄75；152等品种的偶合组分。
还可作为染料和颜料中间体产品，以及染料、有机颜料中间体。

类别
有毒物品

毒性分级
高毒

急性毒性
口服 - 大鼠 LD₅₀: 176 毫克/公斤

可燃性危险特性
可燃；加热分解时释放有毒氮氧化物烟雾

储运特性
库房应保持通风、低温和干燥环境

灭火剂
干粉、泡沫、砂土、二氧化碳或雾状水

反应信息

• 作为反应物：
  描述：

  对乙氧基-N-乙酰乙酰苯胺 在 甲醇 、 镍 作用下， 生成 羟丁酰胺苯醚
  参考文献：
  名称：

  beta-hydroxybutyric acid para-phenetidide and a process for preparing it

  摘要：

  公开号：

  US02830087A1
• 作为产物：
  描述：

  双乙烯酮 、 对乙氧基苯胺 在 三乙胺 作用下， 以 苯 为溶剂， 以93%的产率得到对乙氧基-N-乙酰乙酰苯胺
  参考文献：
  名称：

  Inhibitors of Tick-Borne Flavivirus Reproduction from Structure-Based Virtual Screening

  摘要：

  Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]-thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK. cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.

  DOI：

  10.1021/ml400226s

文献信息

• Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
  作者：Zhiguo Zhang、Xiaolong Gao、Haifeng Yu、Guisheng Zhang、Jianming Liu

  DOI：10.1002/adsc.201800616

  日期：2018.9.3

  A copper‐catalysed (diacetoxyiodo)benzene‐promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open‐air conditions and afforded methyl 2‐oxo‐2‐(phenylamino)acetates in good to excellent yields combined with C−C σ‐bond cleavage

  开发了铜催化（二乙酰氧基碘）苯促进的乙酰乙酰胺需氧酯化反应，以合成草酸盐，草酸盐在合成有机化学中是有用的前体。这种实用且温和的合成方法在露天条件下于25°C进行，提供了具有良好或优异收率的2-氧代-2-（苯基氨基）乙酸甲酯，并带有C-Cσ-键裂解和正式的C-H氧化键功能化。提出了一种机制。
• Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds
  作者：Lin Tang、Zhen Yang、Jingchao Jiao、Ying Cui、Guodong Zou、Qiuju Zhou、Yuqiang Zhou、Weihao Rao、Xiantao Ma

  DOI：10.1021/acs.joc.9b01808

  日期：2019.8.16

  achieved, affording a variety of 2-fluoro- and 2,2-difluoro-1,3-dicarbonyl compounds in good to excellent yields. The reaction can be readily performed in aqueous media without any catalyst and base, which features practical and convenient fluorination. Importantly, a gram-scale reaction, transformation of 2-fluoro-1,3-diphenylpropane-1,3-dione to 4-fluoro-1,3,5-triphenyl-1H-pyrazole, and chlorination

  通过改变Selectfluor的数量，已实现了1,3-二羰基化合物的高选择性单氟化和二氟化，从而提供了各种类型的2-氟-和2,2-二氟-1,3-二羰基化合物。产量。该反应可以在没有任何催化剂和碱的水性介质中容易地进行，其特征在于实用且方便的氟化。重要的是，克级反应，将2-氟-1,3-二苯基丙烷-1,3-二酮转化为4-氟-1,3,5-三苯基-1 H-吡唑，以及氯化和溴化1，实现了3-二羰基化合物以进一步显示其合成用途。
• Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-<i>N</i>-phenylacetamides
  作者：Wei-Bing Liu、Cui Chen、Qing Zhang、Zhi-Bo Zhu

  DOI：10.3762/bjoc.8.38

  日期：——

  cleavage of a carbon-carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides.

  报道了一种直接制备 2,2-二卤代-N-苯基乙酰胺的新型可靠方法。关键的转变涉及在 DIB 和路易斯酸作为卤源的情况下裂解碳-碳键，因此该方法显着扩展了 DIB 作为化学合成中独特而强大的工具的价值。该协议不仅为使用其他高价碘试剂的反应增加了一个新的方面，而且为双取代乙酰胺的合成提供了广阔的空间。
• Approach for the Direct Synthesis of<i>β</i>-Dichlorosubstituted Acetanilides Using Iodine Trichloride (ICl₃) as the Oxidant and Catalyst
  作者：Qing Zhang、Weibing Liu、Cui Chen、Liquan Tan

  DOI：10.1002/cjoc.201300007

  日期：2013.4

  A reliable method for direct synthesis of β‐dichlorosubstituted acetanilides is reported. The key transformation involves the oxidative and catalytic cleavage of a carbon‐carbon bond in the presence of iodine trichloride (ICl3). In this protocol ICl3 is used not only as the catalyst but also as the oxidant which widely broadens the scope of its application in organic synthetic chemistry.

  报道了一种直接合成β-二氯取代的乙酰苯胺的可靠方法。关键的转变涉及在三氯化碘（ICl 3）存在下碳-碳键的氧化和催化裂解。在该方案中，ICl 3不仅用作催化剂，还用作氧化剂，广泛地拓宽了其在有机合成化学中的应用范围。
• An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P₂O₅ and catalyzed by zinc bromide
  作者：Liquan Tan、Peng Zhou、Cui Chen、Weibing Liu

  DOI：10.3762/bjoc.9.304

  日期：——

  is presented for the synthesis of polysubstituted 4-pyridones and 2-pyridones from beta-keto amides. A variety of beta-keto amides are used in this approach, and a wide range of functionalized 4-pyridones and 2-pyridones were obtained in good to excellent yields. When employing the N-aryl beta-keto amides as the substrates in this protocol, 4-pyridones are resulted, however, when using N-aliphatic-substituted

  提出了一种由五氧化二磷 (P2O5) 介导并由溴化锌 (ZnBr2) 催化的自缩合环化反应，用于从 β-酮酰胺合成多取代的 4-吡啶酮和 2-吡啶酮。在该方法中使用了多种 β-酮酰胺，并以良好到极好的收率获得了范围广泛的官能化 4-吡啶酮和 2-吡啶酮。在本协议中使用 N-芳基 β-酮酰胺作为底物时, 会产生 4-吡啶酮, 然而, 当使用 N-脂肪族取代的 β-酮酰胺作为 N-芳基 β-酮酰胺的伙伴时,条件下，得到2-吡啶酮。

表征谱图