N-(2-羟乙基)马来酰亚胺 | 1585-90-6

• 物质功能分类: 催化剂及助剂 - 聚合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N-(2-羟乙基)马来酰亚胺
• 中文别名: 1-(2-羟基乙基)-吡咯-2,5-二酮；N-羟乙基马来酰亚胺
• 英文名称: 1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione
• 英文别名: N-(2-hydroxyethyl)-maleimide；N-(hydroxyethyl)maleimide；2-hydroxyethylmaleimide；1-(2-hydroxyethyl)pyrrole-2,5-dione；maleimido ethanol；HEMI
• CAS: 1585-90-6
• 化学式: C₆H₇NO₃
• mdl: MFCD00465266
• 分子量: 141.126
• InChiKey: AXTADRUCVAUCRS-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67 °C (lit.) 67-74 °C
• 沸点：
  130°C/0.005mmHg(lit.)
• 密度：
  1.395

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R36
• WGK Germany：
  3
• 海关编码：
  2925190090
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  | 室温 |

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-(2-Hydroxyethyl)maleimide
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 1585-90-6
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
Eye irritation (Category 2), H319
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R36
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H319 Causes serious eye irritation.
Precautionary statement(s)
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 1-(2-Hydroxyethyl)maleimide
N-(Ethanol)maleimide
1-(2-Hydroxyethyl)-pyrrole-2,5-dione
HEMI
Formula : C6H7NO3
Molecular Weight : 141,12 g/mol
CAS-No. : 1585-90-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
N-(2-Hydroxyethyl)maleimide
Eye Irrit. 2; H319 -
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
N-(2-Hydroxyethyl)maleimide
Xn, R22 - R36 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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 vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Light sensitive.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
impervious clothing, 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).
Control of environmental exposure
Do not let product enter drains.

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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 Melting point/range: 67 - 74 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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: -1,559
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
no data available
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
Additional Information
RTECS: Not available
burning sensation, Cough, wheezing, laryngitis, Shortness of breath, Headache, Nausea, Vomiting, To the
best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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. 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-(2-羟乙基)马来酰亚胺是一种交联剂，常用于化学合成中。

反应信息

• 作为反应物：
  描述：

  N-(2-羟乙基)马来酰亚胺 以 乙醚 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 1-<2-<3-propylthio-1-(2,5-dioxpyrrolidinyl)>ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Litak, Peter T.; Kauffman, Joel M., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480

  摘要：

  DOI：
• 作为产物：
  描述：

  C₁₀H₁₁NO₄ 以 甲苯 为溶剂， 反应 10.0h， 以54%的产率得到N-(2-羟乙基)马来酰亚胺
  参考文献：
  名称：

  合成功能化碱性马来酰亚胺的有效方法

  摘要：

  提出了一个三步程序，涉及马来酸酐与呋喃的Diels-Alder缩合反应，与适当的二胺反应后形成N-取代的酰亚胺，以及马来碳-碳双键的最终Diels-Alder再生，以实现明确的合成。的ñ取代基本马来酰亚胺。该新方法的特点是反应条件温和，易于操作，收率高且无需额外的催化作用。

  DOI：

  10.1002/jhet.1651

文献信息

• CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF
  申请人：PFIZER INC.

  公开号：US20130129753A1

  公开（公告）日：2013-05-23

  The present invention is directed to cytotoxic pentapeptides, to antibody drug conjugates thereof, and to methods for using the same to treat cancer.

  本发明涉及细胞毒性五肽，其抗体药物偶联物，以及使用它们治疗癌症的方法。
• [EN] CONJUGATES FOR TREATING DISEASES<br/>[FR] CONJUGUÉS POUR LE TRAITEMENT DE MALADIES
  申请人：ENDOCYTE INC

  公开号：WO2016148674A1

  公开（公告）日：2016-09-22

  The present disclosure relates to pyrrolobenzodiazepine (PBD) prodrugs and conjugates thereof. The present disclosure also relates to pharmaceutical compositions of the conjugates described herein, methods of making and methods of using the same.

  本公开涉及吡咯苯并二氮杂环（PBD）前药及其结合物。本公开还涉及所述结合物的药物组合物，制备方法和使用方法。
• [EN] ANTIBODY CONJUGATES COMPRISING TOLL-LIKE RECEPTOR AGONIST AND COMBINATION THERAPIES<br/>[FR] CONJUGUÉS D'ANTICORPS COMPRENANT UN AGONISTE DU RÉCEPTEUR DE TYPE TOLL ET POLYTHÉRAPIES
  申请人：NOVARTIS AG

  公开号：WO2018198091A1

  公开（公告）日：2018-11-01

  Provided herein are antibody conjugates comprising toll-like receptor agonists and the use of such conjugates for the treatment of cancer. In some embodiments, the conjugates comprise anti-HER2 antibodies. In some embodiments, the conjugates are used in combination with a second therapeutic agent.

  本文提供了包含Toll样受体激动剂的抗体偶联物，以及利用这些偶联物治疗癌症的用途。在某些实施例中，这些偶联物包括抗HER2抗体。在某些实施例中，这些偶联物与第二治疗剂联合使用。
• [EN] DC-SIGN ANTIBODY DRUG CONJUGATES<br/>[FR] CONJUGUÉ MÉDICAMENT-ANTICORPS ANTI-DC-SIGN
  申请人：NOVARTIS AG

  公开号：WO2020089811A1

  公开（公告）日：2020-05-07

  Provided herein are antibodies to DC-SIGN, conjugates of DC-SiGN antibodies, and DC-SiGN antibody fusion proteins and the use of such antibodies, conjugates, and fusion proteins for the treatment of diseases such as cancer.

  本文提供了针对DC-SIGN的抗体，DC-SIGN抗体的结合物，以及DC-SIGN抗体融合蛋白，以及利用这些抗体、结合物和融合蛋白治疗癌症等疾病的用途。
• QUENCHER
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：US20170342031A1

  公开（公告）日：2017-11-30

  A quencher is disclosed having a compound represented by the following general formula (1): wherein R 5 each independently represent a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an amino group having a substituent or not having a substituent, a hydroxy group, an aryl group, an aryloxy group, or an arylalkyl group; R 6 represents a group having a polymerizable unsaturated group, a hydroxy group, or the like; Y 1 represents an oxygen atom, or the like; An − represents an anion; Ar 1 represents a specific ring structure; * and ** represent binding positions; Ar 2 represents a benzene ring, a naphthalene ring, or an anthracene ring; n 1 represents a specific integer; and the following structure (1-10) in the general formula (1) is an asymmetric structure; (wherein R 5 , Y 1 , Ar 1 , Ar 2 , n 1 , * and ** are the same as described above.).

  一种淬灭剂被公开，该淬灭剂具有以下一般公式(1)表示的化合物： 其中R5各自独立代表一个卤素原子、一个烷基团、一个烷氧基团、一个烷硫基团、一个带有或不带有取代基的氨基团、一个羟基、一个芳基团、一个芳氧基团或一个芳烷基团；R6代表一个具有可聚合不饱和基团、一个羟基或类似基团的集团；Y1代表一个氧原子或类似；An代表一个阴离子；Ar1代表一个特定的环结构；*和**代表结合位置；Ar2代表一个苯环、一个萘环或一个蒽环；n1代表一个特定的整数； 并且一般公式(1)中的以下结构(1-10)是一个不对称结构； (其中R5、Y1、Ar1、Ar2、n1、*和**与上述描述相同)。

表征谱图