2',4'-二甲氧基乙酰乙酰苯胺 | 16715-79-0

• 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: 2',4'-二甲氧基乙酰乙酰苯胺
• 中文别名: 2,4-二甲氧基乙酰乙酰替苯胺
• 英文名称: N-(2,4-dimethoxyphenyl)-3-oxobutanamide
• 英文别名: 2',4'-Dimethoxyacetoacetanilide
• CAS: 16715-79-0
• 化学式: C₁₂H₁₅NO₄
• mdl: MFCD00043929
• 分子量: 237.255
• InChiKey: IQWUCASGTZCNKK-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  413.7±40.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 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：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn,Xi
• 危险类别码：
  R22,R20/21/22,R36/37/38
• WGK Germany：
  2
• 海关编码：
  2924299090
• 危险类别：
  6.1
• 安全说明：
  S26,S28,S36/37/39,S36/39
• 包装等级：
  III
• 危险品运输编号：
  2810
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

2',4'-Dimethoxyacetoacetanilide Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2',4'-Dimethoxyacetoacetanilide

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Category 4
Acute toxicity (Dermal)
Acute toxicity (Inhalation) Category 4
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Harmful if swallowed, in contact with skin or if inhaled
Precautionary statements:
Avoid breathing dust/fume/gas/mist/vapours/spray.
[Prevention]
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Call a POISON CENTER or doctor/physician if you feel unwell.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF ON SKIN: Gently wash with plenty of soap and water.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2',4'-Dimethoxyacetoacetanilide
Percent: >95.0%(N)
16715-79-0
CAS Number:
Chemical Formula: C12H15NO4
2',4'-Dimethoxyacetoacetanilide

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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.
Call a POISON CENTER or doctor/physician if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
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: Call a POISON CENTER or doctor/physician if you feel unwell. 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
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: 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
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: 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
Precautions for safe 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 local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
2',4'-Dimethoxyacetoacetanilide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Form: Crystal- Powder
Colour: Pale yellow - Greyish yellow red
Odour: No data available
pH: No data available
Melting point/freezing point:96°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
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: Does not correspond to the classification standard of the United Nations
2',4'-Dimethoxyacetoacetanilide

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Section 14. TRANSPORT INFORMATION
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): 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

反应信息

• 作为反应物：
  描述：

  2',4'-二甲氧基乙酰乙酰苯胺 在 碘苯二乙酸 、 zinc(II) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以77%的产率得到2-(2,4-dimethoxyphenyl)-5-methylisoxazole-3(2H)-one
  参考文献：
  名称：

  通过高价碘介导的氧化锌（ZnO）催化的3-氧-N-苯基丁酰胺的串联串联氧化环化反应， 直接构建5-甲基-2-苯基异恶唑-3（2 H）-ones †

  摘要：

  一系列的组合介导的顺序氧化串联环化反应 （二乙酰氧基碘）苯 （DIB）与 氧化锌（ZnO）被提出用于由β-酮丁基苯胺合成5-甲基-2-苯基异恶唑-3（2 H）-ones。此方法中使用了多种β-酮丁基苯胺化合物，并以良好或优异的收率获得了多种官能化的5-甲基异恶唑-3（2 H）-酮。

  DOI：

  10.1039/c2ob27145a
• 作为产物：
  描述：

  丁-1-烯-1,3-二酮 、 2,4-二甲氧基苯胺 以 苯 为溶剂， 以80%的产率得到2',4'-二甲氧基乙酰乙酰苯胺
  参考文献：
  名称：

  Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities

  摘要：

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

  DOI：

  10.1021/jm801335z

文献信息

• Pigment compositions for solvent and water-based ink systems and the methods for producing them
  申请人：HOECHST CELANESE CORPORATION

  公开号：EP0592907A1

  公开（公告）日：1994-04-20

  This invention is an azo pigment composition containing a water insoluble metal salt of a water soluble polymer; a method of preparing said composition and ink compositions prepared from said azo pigment compositions.

  这项发明是一种含有水不溶性金属盐的水溶性聚合物的偶氮颜料组合物；一种制备该组合物的方法以及由该偶氮颜料组合物制备的油墨组合物。
• The preparation of 4-oxo-<i>N</i>-aryl-4<i>H</i>-1-benzopyran-2-acetamides by the condensation/cyclization of trilithiated acetoacetanilides with lithiated methyl salicylates
  作者：Douglas R. Hurst、Kristen L. French、April J. Angel、Angela R. Williams、Mary E. Rampey、Tina S. Guion、Kam W. Chan、Camille M. Kassis、Shannon L. Studer Martinez、Charles F. Beam

  DOI：10.1002/jhet.5570350622

  日期：1998.11

  Several acetoacetanilides were trilithiated in excess lithium diisopropylamide, and the resulting polylithiated intermediates were regioselectively condensed with lithiated methyl salicylates followed by acid cyclization to substituted 4-oxo-N-aryl-4H-1-benzopyran-2-acetamides (benzopyranone-2-acetamides).

  在过量的二异丙基氨基锂中将数个乙酰乙酰苯胺三锂化，然后将所得的多锂化中间体与锂化的水杨酸甲酯区域选择性地缩合，然后酸环化成取代的4-氧代-N-芳基-4 H -1-苯并吡喃-2-乙酰胺（苯并吡喃酮-2-乙酰胺）。
• 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 Five‐Component Reaction for the Synthesis of 4,4′‐((2‐Oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1 <i>H</i> ‐pyrrolo[3,4‐ <i>c</i> ]quinoline‐1,3(2 <i>H</i> )‐dione) Derivatives
  作者：Kaimin Mao、Lei Dai、Yun Liu、Liangce Rong

  DOI：10.1002/jhet.3592

  日期：2019.8

  cascade process five‐component reaction of isatins and 3‐oxo‐N‐arylbutanamide for the synthesis of 4,4′‐((2‐oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1H‐pyrrolo[3,4‐c]quinoline‐1,3(2H)‐dione) derivatives was reported under mild condition. The advantages of this strategy are easy to obtain raw materials, convenient one‐pot procedure, and simple operation.

  靛红与3-氧代-N-芳基丁酰胺的高效级联反应五组分反应，用于合成4,4'-（（2-氧代吲哚啉-3,3-二基）双（亚甲基）双（2-芳基）据报道在温和条件下有1 H-吡咯并[3,4- c ]喹啉-1,3（2 H）-dione）衍生物。该策略的优点是易于获取原材料，方便的单锅法和简单的操作。

表征谱图