N-苄基-2,3-二溴马来酰亚胺 | 91026-00-5

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-苄基-2,3-二溴马来酰亚胺
• 中文别名: 1-苄基-3,4-二溴-吡咯-2,5-二酮；N-苯甲基-2,3-二溴马来酰亚胺
• 英文名称: N-benzyl-2,3-dibromo-maleimide
• 英文别名: 3,4-dibromo-2,5-dihydro-1-benzyl-1H-pyrrole-2,5-dione；1-benzyl-3,4-dibromo-1H-pyrrole-2,5-dione；3,4-dibromo-1-benzyl-1H-pyrrole-2,5-dione；1-benzyl-3,4-dibromopyrrole-2,5-dione；2,3-dibromo-N-(phenylmethyl)maleimide；2,3-dibromo-N-benzylmaleimide；N-Benzyl-2,3-dibromomaleimide
• CAS: 91026-00-5
• 化学式: C₁₁H₇Br₂NO₂
• 分子量: 344.99
• InChiKey: DZYLZHRCCNTQCS-UHFFFAOYSA-N

物化性质

• 熔点：
  117-120 °C(lit.)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂、强酸或强还原剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34,R43
• 危险品运输编号：
  UN 1759 8/PG 2
• 海关编码：
  2925190090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H314,H317
• 储存条件：
  请将贮藏器密封，并将其放入一个紧密的容器中。存放在阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-Benzyl-2,3-dibromomaleimide
CAS-No. : 91026-00-5
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 corrosion (Category 1B)
Skin sensitization (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Causes burns. May cause sensitization by skin contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H314 Causes severe skin burns and eye damage.
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R34 Causes burns.
R43 May cause sensitization by skin contact.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 1-Benzyl-3,4-dibromo-pyrrole-2,5-dione
Formula : C11H7Br2NO2
Molecular Weight : 344,99 g/mol
Component Concentration
N-Benzyl-2,3-dibromomaleimide
CAS-No. 91026-00-5 -

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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
Take off contaminated clothing and shoes immediately. 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
Do NOT induce vomiting. 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
Cough, Shortness of breath, Headache, Nausea, Vomiting
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), Hydrogen bromide gas
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. Evacuate personnel to safe areas. 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.
Moisture sensitive.
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
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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: crystalline
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 117 - 120 °C - lit.
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- no data available
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, Strong acids, Strong bases, Strong reducing 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.
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. Material is extremely destructive to the tissue of
the mucous membranes and upper respiratory tract.
Ingestion May be harmful if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
Signs and Symptoms of Exposure
Cough, Shortness of breath, Headache, Nausea, Vomiting
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: 1759 IMDG: 1759 IATA: 1759
UN proper shipping name
ADR/RID: CORROSIVE SOLID, N.O.S. (N-Benzyl-2,3-dibromomaleimide)
IMDG: CORROSIVE SOLID, N.O.S. (N-Benzyl-2,3-dibromomaleimide)
IATA: Corrosive solid, n.o.s. (N-Benzyl-2,3-dibromomaleimide)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: II IMDG: II IATA: II
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

反应信息

• 作为反应物：
  描述：

  N-苄基-2,3-二溴马来酰亚胺 在 palladium on activated charcoal 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 3,4-bis[5-(diethoxymethyl)fur-2-yl]-2,5-dihydro-1-benzyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  取代的双（杂芳基）马来酰亚胺的合成

  摘要：

  描述了具有潜在抗糖尿病特性的取代的双（呋喃-2-基），双（呋喃-3-基）和双（噻吩-2-基）马来酰亚胺。作为关键步骤，它们的合成涉及各种硼衍生物与二碘亚胺之间的铃木交叉偶联。因此，可以制备各种取代的对称和非对称马来酰亚胺衍生物。

  DOI：

  10.1016/j.tet.2005.03.016
• 作为产物：
  描述：

  N-苄基马来酰亚胺 在 lithium perchlorate 、 sodium bromide 作用下， 以 aq. phosphate buffer 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以69%的产率得到N-苄基-2,3-二溴马来酰亚胺
  参考文献：
  名称：

  一种3,4-二溴马来酰亚胺的电化学合成方法

  摘要：

  本发明涉及有机合成技术领域，尤其涉及一种3,4‑二溴马来酰亚胺的电化学合成方法，以马来酰亚胺为起始原料，以廉价、安全易得的溴化物为溴源，在阳极室中一锅得到3,4‑二溴马来酰亚胺，操作简单，绿色友好，反应条件温和，并且原料便宜易得，可以有效地降低生产成本。电化学反应是通过反应物在电极上得失电子实现的，不用加入额外的氧化剂，金属催化剂，减少了物质消耗，从而减少了环境污染；反应在常温常压下进行，这对节约能源、降低设备投资十分有利；工艺流程简单，操作简便，反应容易控制，一锅反应即可得到3,4‑二溴马来酰亚胺；所使用的溴化物廉价易得，减少了原料成本，且使用时十分安全；反应过程绿色友好，符合绿色化学工艺的要求。

  公开号：

  CN112795943A

文献信息

• A facile synthesis of staurosporine aglycone
  作者：Guojian Xie、J. William Lown

  DOI：10.1016/s0040-4039(00)77245-5

  日期：1994.8

  A highly efficient method is described for the synthesis of staurosporine aglycone 3 from the readily available dibromomaleic acid in six steps.

  描述了一种高效的方法，该方法可通过六个步骤从容易获得的二溴马来酸合成星形孢菌素苷元3。
• The Spermine–Bisaryl Conjugate as a Potent Inducer of B‐ to Z‐DNA Transition
  作者：Issei Doi、Genichiro Tsuji、Kyoko Kawakami、Osamu Nakagawa、Yosuke Taniguchi、Shigeki Sasaki

  DOI：10.1002/chem.201000947

  日期：2010.10.18

  cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. Using isothermal titration calorimetry (ITC) we show that the B→Z transition induced by 3 c is both enthalpically and entropically favorable. The ligand might effect the dehydration of B‐DNA, which leads to the B→Z transition. Interestingly, an intermediate CD between the B and Z forms was observed in the pH‐dependent transition in the

  含有交替的嘌呤和嘧啶重复序列的DNA具有采用Z‐DNA结构的潜力，Z‐DNA结构是除A‐DNA和B‐DNA之外广为研究的结构之一。尽管已经提出了许多分子模型来解释B→Z转变的机理，但是关于这种转变的机理和生理作用的讨论仍在继续。在这项研究中，我们发现在低盐浓度下，双（2-萘基）-马来酰亚胺-精胺结合物（3 c）具有引起d（CGCGCG）2从B→Z转变的显着能力。使用等温滴定热法（ITC），我们显示了3 c诱导的B→Z跃迁在焓和熵上都是有利的。配体可能会影响B‐DNA的脱水，从而导致B→Z过渡。有趣的是，在配体存在的情况下，在pH依赖性转变中观察到了B和Z形式之间的中间CD。在这项研究中设计的配体的独特结构和特征将对Z‐DNA的研究有用。
• [EN] TYPE III DEIODINASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA DÉSIODINASE DE TYPE III ET LEURS UTILISATIONS
  申请人：HADASIT MED RES SERVICE

  公开号：WO2015140792A1

  公开（公告）日：2015-09-24

  The present invention relates to compounds that inhibit the activity of Type III deiodinase (DIO3). The present invention further relates to methods for treating or preventing depression, depression associated with other psychiatric or general medical diseases or conditions, condition amenable to treatment with known anti-depressants and cancer, particularly by using the compounds of the invention.

  本发明涉及抑制第三型去碘酶（DIO3）活性的化合物。本发明还涉及治疗或预防抑郁症、与其他精神疾病或一般医学疾病相关的抑郁症、适合使用已知抗抑郁药物治疗的疾病或状况，以及癌症的方法，特别是通过使用本发明的化合物。
• Revised Structures of <i>N</i>-Substituted Dibrominated Pyrrole Derivatives and Their Polymeric Products. Termaleimide Models with Low Optical Band Gaps
  作者：Dong-Sook Choi、Shenlin Huang、Mingsheng Huang、Thomas S. Barnard、Richard D. Adams、Jorge M. Seminario、James M. Tour

  DOI：10.1021/jo9722055

  日期：1998.4.1

  bromides migrate from the 2,5-positions to the 3,4-positions with subsequent oxidation at the 2,5-positions to afford N-substituted 3,4-dibromomaleimides; the structure was confirmed by single-crystal X-ray analysis. The maleimides were then polymerized to the poly(N-substituted-3,4-maleimide)s with copper bronze. This constitutes a revision of structure for the monomers and polymers. The propensity

  本文介绍了HNO（3）处理后N-取代的2,5-二溴吡咯的意外重排/氧化。溴化物从2,5-位迁移到3,4-位，随后在2,5-位氧化，得到N-取代的3,4-二溴马来酰亚胺；通过单晶X射线分析确认了结构。然后用铜青铜将马来酰亚胺聚合成聚（N-取代的3，4-马来酰亚胺）。这构成了单体和聚合物结构的修订。通过在非氧化酸性条件下（p-TsOH）处理N-苄基-2，5-二溴吡咯得到N-苄基-3，4-二溴吡咯，进一步证实了二溴化物的迁移倾向。原材料和产物结构均通过单晶X射线分析确定。从吡咯中制备了几种亚氨基酰亚胺，马来酸酐和柠康酸酐。当添加碱或亲核溶剂时，这些三聚体化合物的最大吸光度发生变化（约200 nm）。因此，对于那些在使用相同的添加剂处理后发生了350-400 nm的位移的聚合物体系，这些末端酰亚胺是很好的模型。从头算起就用Hartree-Fock和密度泛函理论来评估三聚体系统的最小构象。相对于中央
• Strain‐Promoted Azide–Alkyne Cycloaddition with Ruthenium(II)–Azido Complexes
  作者：Thomas Cruchter、Klaus Harms、Eric Meggers

  DOI：10.1002/chem.201302502

  日期：2013.12.2

  the determined second‐order rate constant for the ADIBO cycloaddition with the azido complex (k2=6.9 × 10−2 M−1 s−1) is comparable to the rate determined for the ADIBO cycloaddition with organic benzyl azide (k2=4.0 × 10−1 M−1 s−1). Our results demonstrate that it is possible to transfer the concept of strain‐promoted azide–alkyne cycloaddition (SPAAC) from purely organic azides to metal‐coordinated

  研究了示例性的钌（II）-叠氮基络合物在室温和低叠氮化物和炔烃浓度下对未活化的，电子不足的以及对应变活化的炔烃的反应性。在这种条件下，即使在铜（I）催化条件下，未活化的末端炔烃和内部炔烃也无法反应。相反，正如预期的那样，使用缺电子的乙炔二羧酸二甲酯（DMAD）作为双极性亲和剂，观察到了快速的环加成反应。由于DMAD和相关的炔丙基酯是出色的Michael受体，因此不适合生物学应用，因此我们研究了叠氮基络合物与环辛炔（OCT），双环[6.1.0] non-4-yne（BCN）衍生物的环加成反应性，和氮杂二苯并环辛炔（ADIBO）。虽然在应变较小的环辛炔OCT的情况下未观察到反应，但应变较大的环辛炔BCN和ADIBO容易与叠氮基络合物反应，提供了相应的稳定的三唑并合物，可通过常规硅胶柱色谱纯化。获得了ADIBO环加合物的X射线晶体结构，并验证了形成的1,2,3-三唑并配体通过中心N2原子配位金属