m-N-马来酰亚氨基苯甲酸 | 17057-07-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: m-N-马来酰亚氨基苯甲酸
• 中文别名: 3-(2,5-二氧代-2,5-二氢-1H-1-吡咯基)苯甲酸；3-N-马来酰亚氨基苯甲酸；m-N-马来酰亚胺基苯甲酸；3-(2,5-二氢-2,5-二氧代-吡咯-1-基)苯甲酸
• 英文名称: 3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid
• 英文别名: m-N-maleimidobenzoic acid；3-maleinimidobenzoic acid；3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid；N-(3-carboxyphenyl)maleimide；3-maleimido-benzoic acid；3-(2,5-dihydro-2,5-dioxo(1H)-pyrrole-1-yl)benzoic acid；3-Maleinimido-benzoesaeure；3-(2,5-dioxopyrrol-1-yl)benzoic acid
• CAS: 17057-07-7
• 化学式: C₁₁H₇NO₄
• mdl: MFCD00022572
• 分子量: 217.181
• InChiKey: ZJGBFJBMTKEFNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C
• 沸点：
  455.2±28.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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
• 危险品标志：
  Xi
• 海关编码：
  2925190090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-Maleimidobenzoic acid
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]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C11H7NO4
Molecular Weight : 217,18 g/mol
Component Concentration
3-Maleimidobenzoic acid
-

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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
Safety glasses with side-shields conforming to EN166 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: 1,187
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
Strong 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
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals. 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 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.

制备方法与用途

3-maleimidobenzoic酸是一种蛋白质交联剂。

反应信息

• 作为反应物：
  描述：

  m-N-马来酰亚氨基苯甲酸 在 乙酸酐 作用下， 反应 18.0h， 以48%的产率得到m-Maleinimidobenzoesaeureanhydrid
  参考文献：
  名称：

  Synthese von neuen bifunktionellen Maleinimidverbindungen zur Herstellung von Chemoimmunokonjugaten

  摘要：

  Bifunctional maleimide compounds are suitable for binding small molecules to carrier proteins in that they bind to the sulfhydryl group of proteins through the double bond of the maleimide group and to molecules of low molecular weight (e.g. anticancer drugs) through a functional group X. 18 maleimide compounds of the general formula Maleimid-R-X (R = phenylene, benzyl-, methylene-, ethylene, or a m-benzoylethylamide group and X = hydroxp-, amino-, hydrazino-, carboxylic acid-, carboxylic anhydride-, carboxylic acid chloride-, carboxylic acid hydrazide-, oxycarbonylchloride-, aldehyde, keto-, or p-toluenesulfonate-group) were synthesized and characterized through H-1- and C-13-NMR-spectroscopy, elemental analysis, and mass spectrometry.

  DOI：

  10.1007/bf00807643
• 作为产物：
  描述：

  3-[[(2Z)-3-carboxy-1-oxo-2-propen-1-yl]amino]benzoic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 以68%的产率得到m-N-马来酰亚氨基苯甲酸
  参考文献：
  名称：

  设计，合成和生化评估N-取代的马来酰亚胺作为前列腺素内过氧化物合酶的抑制剂。

  摘要：

  N-（羧基烷基）马来酰亚胺是前列腺素内过氧化物合酶（PGHS）的快速抑制剂，也是时间依赖性抑制剂。相应的N-烷基马来酰亚胺仅是PGHS的时间依赖性灭活剂，表明羧酸盐对于快速抑制至关重要。合成了几种具有与非甾体抗炎药阿司匹林相似的结构特征的N-取代的马来酰亚胺类似物，并将其评估为PG​​HS的抑制剂。大多数类似阿司匹林的马来酰亚胺都以类似于阿司匹林的时间和浓度依赖性方式灭活纯化的绵羊PGHS-1的环氧合酶活性。PGHS的过氧化物酶活性也被马来酰亚胺类似物灭活。这些化合物也抑制了诱导型同功酶PGHS-2的环氧合酶活性。N-5-马来酰亚胺基-2-乙酰氧基-1-苯甲酸的相应琥珀酰亚胺类似物不抑制任何一种酶的活性，这表明失活是由于蛋白质的共价修饰。研究了N-（羧基庚基）马来酰亚胺对PGHS-1的抑制作用机理。将apoPGHS-1与2当量的N-（羧基庚基）[3,4-14C]马来酰亚胺一起孵育会导致蛋白

  DOI：

  10.1021/jm950872p

文献信息

• Targeted multivalent macromolecules
  申请人：TARGESOME, INC.

  公开号：US20030129223A1

  公开（公告）日：2003-07-10

  Targeted therapeutic agents, comprising a linking carrier, a therapeutic entity associated with the linking carrier, and at least one targeting entity are provided, as well as methods for their preparation and use.

  靶向治疗剂，包括一个连接载体，与连接载体相关联的治疗实体，以及至少一个靶向实体，以及它们的制备和使用方法。
• CHEMICAL LINKERS AND CLEAVABLE SUBSTRATES AND CONJUGATES THEREOF
  申请人：Sufi Bilal

  公开号：US20100145036A1

  公开（公告）日：2010-06-10

  The present disclosure provides drug-ligand conjugates and drug-cleavable substrate conjugates that are potent cytotoxins. The disclosure is also directed to compositions containing the drug-ligand conjugates, and to methods of treatment using them.

  本公开提供了药物-配体共轭物和药物可切割底物共轭物，它们是有效的细胞毒素。该公开还涉及含有药物-配体共轭物的组合物，以及使用它们的治疗方法。
• Synthetic and biological studies on some new camphor thiazolidinones
  作者：Ahmed M. Abo-Bakr、Entesar A. Hassan、Al-Hassan S. Mahdy、Salem E. Zayed

  DOI：10.1007/s13738-021-02228-6

  日期：2021.10

  1 with ethyl bromoacetate, dimethyl acetylenedicarboxylate and maleic anhydride afforded the corresponding thiazolidinone 2, thiazolidinylidene acetate 3 and thiazolidinyl acetic acid 4, respectively. The acid 4 underwent esterification to afford the ester 5. Treatment of compounds 2, 3 and 5 with appropriate reagents afforded the newly camphor thiazolidinone derivatives 6a,b–14a,b. The elemental analysis

  摘要 樟脑缩氨基硫脲1用于合成新的噻唑烷酮。因此，1与溴乙酸乙酯、乙炔二甲酸二甲酯和马来酸酐的反应分别得到相应的噻唑烷酮2、噻唑烷乙酸酯3和噻唑烷乙酸酯4。酸4经历酯化以提供酯5。化合物的治疗2，3和5用适当的试剂，得到新樟脑噻唑烷酮衍生物6A，B - 14A，B。元素分析，FT-IR，1H NMR、13 C NMR 和质谱证实了新噻唑烷酮的化学结构。研究了一些选定的衍生物作为抗菌剂和抗真菌剂的潜在用途，并给出了有希望的结果。 图形摘要
• Synthesis, anticholinesterase activity and structure–Activity relationships of m-Aminobenzoic acid derivatives
  作者：José Trujillo-Ferrara、Leticia Montoya Cano、Michel Espinoza-Fonseca

  DOI：10.1016/s0960-894x(03)00198-7

  日期：2003.5

  The synthesis, acetylcholinesterase inhibitory capacity and structure-activity relationships of simple-structured m-Aminobenzoic acid derivatives are reported. Compound 1b was found to be more potent than galanthamine and tacrine in inhibiting acetylcholinesterase.

  报道了简单结构的间氨基苯甲酸衍生物的合成，乙酰胆碱酯酶的抑制能力和结构-活性关系。发现化合物1b在抑制乙酰胆碱酯酶方面比加兰他敏和他克林更有效。
• [EN] COMPOSITIONS AND METHODS FOR TREATMENT OF PROTEINOPATHIES<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE PROTÉINOPATHIES
  申请人：INTELLECT NEUROSCIENCES INC

  公开号：WO2013063086A1

  公开（公告）日：2013-05-02

  This invention relates to antibody drug conjugates and methods of use thereof. More particularly, antibody drug conjugates comprising a cytoprotective agent are provided, wherein the conjugates are useful for the treatment of proteinopathies such as Alzheimer's disease.

  这项发明涉及抗体药物偶联物及其使用方法。更具体地，提供了包含细胞保护剂的抗体药物偶联物，其中这些偶联物可用于治疗蛋白质病，如阿尔茨海默病。