N-丙酮基邻苯二甲酰亚胺 | 3416-57-7

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-丙酮基邻苯二甲酰亚胺
• 中文别名: 2-(2-氧代丙基)异吲哚啉-1,3-二酮；邻苯二甲酰亚胺基丙酮
• 英文名称: N-acetonylphthalimide
• 英文别名: 1-N-Phthalimidopropan-2-on；2-(2-oxopropyl)isoindoline-1,3-dione；Phthalimidoacetone；2-(2-oxopropyl)isoindole-1,3-dione
• CAS: 3416-57-7
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00088346
• 分子量: 203.197
• InChiKey: STMRGLKPBJVVEG-UHFFFAOYSA-N

物化性质

• 熔点：
  123°C
• 沸点：
  341.1±25.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DMF
• 稳定性/保质期：
  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险类别码：
  R36/37/38
• 海关编码：
  2925190090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

Phthalimidoacetone Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Phthalimidoacetone

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Phthalimidoacetone
Percent: >98.0%(LC)
CAS Number: 3416-57-7
Synonyms: N-Acetonylphthalimide , 1-(N-Phthalimidyl)-2-propanone
Chemical Formula: C11H9NO3

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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.
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: Get medical advice/attention 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.
Phthalimidoacetone

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Section 5. FIRE-FIGHTING MEASURES
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
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
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.
Hand protection: Protective gloves.
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
Form: Crystal- Powder
Colour: White - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:123°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]
Methanol, Acetone
Soluble:
Phthalimidoacetone

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

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
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
Not listed
UN-No:

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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.
Phthalimidoacetone

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-丙酮基邻苯二甲酰亚胺 在 [NMe2H2][{RuCl((S)-C3-TunePhos)}2(μ-Cl)3] 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、10.0 MPa 条件下， 反应 72.0h， 生成 (S)-(+)-1-邻苯二甲酰-2-丙醇
  参考文献：
  名称：

  α-邻苯二甲酰亚胺酮的高度对映选择性不对称氢化：对映体纯氨基醇的有效入口

  摘要：

  以Ru-(C3-TunePhos)配合物为催化剂，以优异的对映选择性氢化一种新型α-邻苯二甲酰亚胺酮。在氢化反应中，超过 99% ee 的转化率达到了 10 000 次。对苏氨酸的合成进行了动态动力学拆分研究，首次观察到了高抗选择性（>97:3）。已开发出一种合成对映体纯氨基醇的有效方法。

  DOI：

  10.1021/ja039153n
• 作为产物：
  描述：

  N-丙炔基邻苯二甲酸胺 在 [RhCl2(p-cymene)]2 、 水 作用下， 反应 24.0h， 以88%的产率得到N-丙酮基邻苯二甲酰亚胺
  参考文献：
  名称：

  PEG-400 中钌 (II) 催化的末端炔烃水合

  摘要：

  报道了在 PEG-400 中钌 (II) 催化的末端炔烃的水合作用，通过在炔烃上加入马尔可夫尼科夫水生成甲基酮。

  DOI：

  10.1055/s-0035-1561864
• 作为试剂：
  描述：

  Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 、 L-脯氨酸 在 N-丙酮基邻苯二甲酰亚胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以59%的产率得到
  参考文献：
  名称：

  方便的手性1,2-和1,4-二胺的合成：直接有机催化不对称曼尼希反应中依赖保护基的区域选择性。

  摘要：

  [反应：见正文]在L-脯氨酸衍生的四唑催化剂存在下，受保护的氨基酮与亚胺的有机催化不对称曼尼希反应提供了优异的收率和高达99％的对映选择性的二胺。氨基酮保护基控制反应的区域选择性，从而提供了来自叠氮基酮的手性1,2-二胺和邻苯二甲酰亚胺基酮的1,4-二胺的通道。

  DOI：

  10.1021/ol060980d

文献信息

• Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst
  作者：Zachary K. Wickens、Bill Morandi、Robert H. Grubbs

  DOI：10.1002/anie.201306756

  日期：2013.10.18

  rules: Reversal of the high Markovnikov selectivity of Wacker‐type oxidations was accomplished using a nitrite co‐catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O‐labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.

  违反规则：使用亚硝酸盐助催化剂逆转了Wacker型氧化的高Markovnikov选择性。可以高收率和醛选择性地氧化无偏的脂肪族烯烃，并且可以容忍多个官能团。18 O标记实验表明，醛O原子源自亚硝酸盐。
• Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
  作者：Yu-Chao Yuan、Raghu Kamaraj、Christian Bruneau、Thierry Labasque、Thierry Roisnel、Rafael Gramage-Doria

  DOI：10.1021/acs.orglett.7b03278

  日期：2017.12.1

  The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

  使用钌催化剂，以高收率和较短的反应时间实现了单步操作中各种合成吸引力的邻苯二甲酰亚胺前所未有的转化为酰胺。机理研究表明，独特的均质途径涉及五元环的打开和CO 2的释放，其中水是质子的来源。
• Pharmacochemistry of Novel Aminoketone Phthalimide, Δ4-Tetrahydrophthalimide, and Arylsuccinimide Derivatives with Local Anaesthetic Activity
  作者：Eleni Sotiropoulou、Panos N. Kourounakis

  DOI：10.1002/ardp.19943270104

  日期：——

  prospective local anaesthetic activity were prepared. The structure of the synthesized compounds was confirmed by spectroscopic and elemental analyses. The physicochemical parameters (pka and logP) were also investigated. The local anaesthetic activity was determined in vitro on sciatic frog's nerve by the compound action potential technique: the phthalimide derivatives possess considerable local anaesthetic

  制备了许多具有预期局部麻醉活性的氨基酮。通过光谱和元素分析确认合成化合物的结构。还研究了理化参数(pka和logP)。采用复合动作电位技术体外测定坐骨蛙神经的局麻活性：邻苯二甲酰亚胺衍生物具有与利多卡因相当而高于普鲁卡因的相当大的局麻活性。
• nBu4NI-Catalyzed oxidative imidation of ketones with imides: synthesis of α-amino ketones
  作者：Yunhe Lv、Yan Li、Tao Xiong、Yu Lu、Qun Liu、Qian Zhang

  DOI：10.1039/c3cc48887j

  日期：——

  nBu4NI-Catalyzed oxidative imidation of ketones and imides for the synthesis of alpha-amino ketones were realized for the first time. The methodology is characterized by its wide substrate scope even for acetone with readily available phthalimide, saccharin and succinimide, which opens a new pathway for direct imidation of ketones.

  首次实现了nBu4NI-催化的酮类和酰亚胺的氧化酰亚胺化和酰亚胺化。该方法的特点是，即使对于丙酮和易得的邻苯二甲酰亚胺，糖精和琥珀酰亚胺，其底物范围也很广，这为直接酰亚胺化酮打开了一条新途径。
• COMPOUND OR ITS TAUTOMER, METAL COMPLEX COMPOUND, COLORED PHOTOSENSITIVE CURING COMPOSITION, COLOR FILTER, AND PRODUCTION
  申请人：MIZUKAWA Yuki

  公开号：US20120238752A1

  公开（公告）日：2012-09-20

  Provided is a colored photosensitive curing composition useful for color filters in primary colors, including blue, green, and red, having a high molar absorption coefficient and allowing a reduction in film thickness and superior color purity and fastness. A colored photosensitive curing composition, comprising, as its colorant, a dipyrromethene-based metal complex compound obtained from a metal or metal compound and a dipyrromethene-based compound represented by the following Formula (I): wherein in Formula (I), R 1 to R 6 each independently represent a hydrogen atom or a substituent group; and R 7 represents a hydrogen or halogen atom, or an alkyl, aryl or heterocyclic group.

  提供的是一种有用于原色彩色滤光片的彩色光敏固化组合物，包括蓝色、绿色和红色，具有高摩尔吸收系数，可减少薄膜厚度，具有优越的颜色纯度和牢固度。 一种彩色光敏固化组合物，包括作为其着色剂的从金属或金属化合物获得的基于二吡咯甲烷的金属配合物化合物和由以下式（I）表示的基于二吡咯甲烷的化合物，其中在式（I）中，R1至R6各自独立地表示氢原子或取代基；R7表示氢或卤素原子，或烷基、芳基或杂环基。

表征谱图