N-(2-羰氧苄基)酞亚胺 | 41513-78-4

• 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-(2-羰氧苄基)酞亚胺
• 中文别名: N-(2-羧基苄基)酞亚胺；2-苯二酰亚胺苯甲酸
• 英文名称: 2-phthalimidobenzoic acid
• 英文别名: N-phthaloyl anthranilic acid；2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-benzoic acid；2-(1,3-dioxoisoindolin-2-yl)benzoic acid；N-(2-Carboxyphenyl)Phthalimide；2-(1,3-dioxoisoindol-2-yl)benzoic acid
• CAS: 41513-78-4
• 化学式: C₁₅H₉NO₄
• mdl: MFCD00041218
• 分子量: 267.241
• InChiKey: RSKJDIQHYKWJLS-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220°C
• 沸点：
  494.2±47.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2925190090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封、阴凉、干燥保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-benzoic
acid
CAS-No. : 41513-78-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin sensitization (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
May cause sensitization by skin contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R43 May cause sensitization by skin contact.
S-phrase(s)
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C15H9NO4
Molecular Weight : 267,04 g/mol
Component Concentration
2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-benzoic acid
CAS-No. 41513-78-4 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,171
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
May cause allergic skin reaction.
The preceding data, or interpretation of data, was determined using Quantitative Structure Activity
Relationship (QSAR) modeling.
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  N-(2-羰氧苄基)酞亚胺 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以84%的产率得到2-[(2-羧基苯甲酰基)氨基]苯甲酸
  参考文献：
  名称：

  pH调节阳离子柱[5]芳烃与反应性2-羧基邻苯二酸之间的客体络合作用对pH的抑制和协同作用

  摘要：

  已经进行了反应性2-羧基邻苯二酸（CPA）和两个阳离子柱芳烃之间的主客体络合研究。仅在较小腔尺寸的柱状芳烃（P5A）中观察到具有显着动力学效应的主客体络合物。在1.50–6.40的pH范围内进行动力学，ESI–MS，1 H NMR滴定和ROESY实验来表征复合物。在所有CPA质子化状态下均观察到高结合化学计量比（H：G 2）。该系统是pH依赖性的，并且通过提高双阴离子CPA 2–的浓度（变构行为）而发生协同作用的反转（负向正）。对于生理pH值，缔合常数K 1：1不变（10 4 M–1），而K 1：2从10 2 M增加到10 4 M –1，并且抑制作用增加到222倍。NMR结果阐明了复合物的结构，使我们能够创建H-H相互作用的图谱，该图很好地描述了复合物中相互作用的多样性和数量。

  DOI：

  10.1021/acs.joc.9b01377
• 作为产物：
  描述：

  2-[(2-羧基苯甲酰基)氨基]苯甲酸 生成 N-(2-羰氧苄基)酞亚胺
  参考文献：
  名称：

  Fuortes; Gaetani, PrΞint.Congr.pure appl.Chem.London 1947,Bd.2,S.85,92

  摘要：

  DOI：

文献信息

• Synthesis of phthalimides, isoindolin-1-ones and isoindolines bearing aminobenzoic acids as a new fluorescent compounds
  作者：Melchor Solis-Santos、Mario Ordóñez、Adrián Ochoa-Terán、Rodrigo Morales-Cueto、Victoria Labastida-Galván

  DOI：10.1016/j.jphotochem.2021.113185

  日期：2021.5

  properties of nine new compounds based on phthalimides, isoindolin-1-ones and isoindolines bearing aminobenzoic acids (2-aminobenzoic acid, 3-aminobenzoic acid and 4-aminobenzoic acid), which were obtained under mild reaction conditions. The photophysical properties of all the compounds were studied by electronic absorption and fluorescence spectroscopy in methanol solutions. All compounds exhibited fluorescence

  为了研究九种基于邻苯二甲酰亚胺，异吲哚啉-1-酮和带有氨基苯甲酸（2-氨基苯甲酸，3-氨基苯甲酸和4-氨基苯甲酸）的异吲哚啉的新化合物的荧光性质，使用了实验方法和理论方法。在温和的反应条件下获得。通过电子吸收和荧光光谱在甲醇溶液中研究了所有化合物的光物理性质。所有化合物均显示出荧光发射和高量子产率。另外，发现这些供体-受体系统中的分子内电荷显着取决于羧酸位置的吸电子取代基。
• Structure activity studies of ring E analogues of methyllycaconitine. Part 2: Synthesis of antagonists to the α3β4* nicotinic acetylcholine receptors through modifications to the ester
  作者：Stephen C Bergmeier、Khadiga A Ismail、Kristjan M Arason、Susan McKay、Darrell L Bryant、Dennis B McKay

  DOI：10.1016/j.bmcl.2004.05.001

  日期：2004.7

  number of simpler analogues of the norditerpeniod alkaloid methyllycaconitine (MLA) in an effort to understand molecular determinants of nAChR*small molecule interactions. We have previously reported the synthesis and evaluation of a series of ring E analogues of MLA. We report here the optimization of the alpha3beta4* functional activity of this series of compounds through modification of the ester.

  用于分化神经元烟碱乙酰胆碱受体（nAChRs）的新型药物的开发对于各种病理状况的治疗很重要。为了了解nAChR *小分子相互作用的分子决定因素，我们已经制备并评估了北二萜生物碱甲基lycaconitine（MLA）的许多简单类似物。我们之前已经报道了一系列MLA的E环类似物的合成和评估。我们在这里报告了通过修饰酯来优化该系列化合物的alpha3beta4 *功能活性的信息。
• An efficient synthesis of quinolones using N-phenyl(triphenylphosphoranylidene)ethenimine
  作者：Pradeep Kumar、Chimmanamada U. Dinesh、Bipin Pandey

  DOI：10.1016/0040-4039(94)88474-9

  日期：1994.12

  acylphosphoranes 5 formed in a highly selective and sequential manner from the reaction of N-substituted anthranilic acids 1 and N-phenyl(triphenylphosphoranylidene)ethenimine 2 undergo intramolecular Wittig cyclization on the imide carbonyl to afford the pyrrolo- and pyrido[1,2-a]quinolones 6 in moderate to good yields.

  所述acylphosphoranes 5从反应形成的以高选择性和顺序方式的N-取代的邻氨基苯甲酸1和N-苯基（三苯基亚正膦）ethenimine 2经历分子内环化反应的Wittig上酰亚胺羰基，得到吡咯和吡啶并[1,2 a]中等至良好产量的喹诺酮类6。
• Nonsteroidal anti-inflammatory drugs and their analogues as inhibitors of aldo-keto reductase AKR1C3: New lead compounds for the development of anticancer agents
  作者：Stanislav Gobec、Petra Brožič、Tea Lanišnik Rižner

  DOI：10.1016/j.bmcl.2005.08.063

  日期：2005.12

  recently identified as potent inhibitors of AKR1C3. We report that some other NSAIDs (diclofenac and naproxen) also inhibit AKR1C3, with the IC(50) values in the low micromolar range. In order to obtain more information about the structure-activity relationship and to identify new leads, a series of compounds designed on the basis of NSAIDs were synthesized and screened on AKR1C3. The most active compounds

  非甾体抗炎药（NSAIDs），如消炎痛，氟苯那酸和相关化合物，最近已被确定为AKR1C3的有效抑制剂。我们报告说，其他一些NSAIDs（双氯芬酸和萘普生）也抑制AKR1C3，其IC（50）值在低微摩尔范围内。为了获得有关构效关系的更多信息并确定新的先导，合成了一系列基于NSAID设计的化合物，并在AKR1C3上进行了筛选。活性最高的化合物是2-[（（2,2-二苯基乙酰基）氨基]苯甲酸4（IC（50）= 11microM）和3-苯氧基苯甲酸10（IC（50）= 0.68microM）。这些化合物代表了开发新的抗癌药的有希望的起点。
• Products from dehydration of dicarboxylic acids derived from anthranilic acid
  作者：Per Wiklund、Ivan Romero、Jan Bergman

  DOI：10.1039/b306032b

  日期：——

  Treatment of N-(carboxymethyl)-anthranilic acids 1 with several dehydrating agents, gave the cyclic ortho amides 6, or the 7-membered anhydrides 7. After reaction of N-(carboxymethyl)-anthranilic acid (1a) with acetic anhydride, a diacetylated fused diketopiperazine indole dimer (18) could be isolated. Dehydrations of 2,2'-iminobis-benzoic acid led to the corresponding cyclic ortho amides 23. The dynamic

  用几种脱水剂处理N-（羧甲基）-邻氨基苯甲酸1，得到环状邻酰胺6或7元酸酐7。N-（羧甲基）-邻氨基苯甲酸（1a）与乙酸酐反应后，可以分离出二乙酰化的稠合的二酮哌嗪吲哚二聚体（18）。2，2′-亚氨基双苯甲酸的脱水导致相应的环状邻酰胺23。研究了其中某些化合物及其前体的动力学行为。