4-马来酰亚胺基苯酚 | 7300-91-6

• 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 - 有机杂环化合物 - 吡咯啉
• 中文名称: 4-马来酰亚胺基苯酚
• 中文别名: 1-(4-羟基苯基)吡咯-2,5-二酮；N-(4-羟基苯基)马来酰亚胺
• 英文名称: N-(4-hydroxyphenyl)maleimide
• 英文别名: N-(p-hydroxyphenyl)-maleimide；4-maleimidophenol；HPMI；1-(4-Hydroxyphenyl)-1H-pyrrole-2,5-dione；1-(4-hydroxyphenyl)pyrrole-2,5-dione
• CAS: 7300-91-6
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: BLLFPKZTBLMEFG-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  397.0±25.0 °C(Predicted)
• 密度：
  1.470±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)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2925190090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  存储于室温且保持在惰性气体环境中

SDS

Name:	1-(4-Hydroxyphenyl)-pyrrole-2 5-dione Material Safety Data Sheet
Synonym:	None Known
CAS:	7300-91-6

Section 1 - Chemical Product MSDS Name:1-(4-Hydroxyphenyl)-pyrrole-2 5-dione Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7300-91-6	1-(4-Hydroxyphenyl)-pyrrole-2,5-dione	100	230-750-6

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.Toxic.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 7300-91-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 286-287 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H7NO3
Molecular Weight: 189.05

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7300-91-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-Hydroxyphenyl)-pyrrole-2,5-dione - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 7300-91-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7300-91-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7300-91-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

4-马来酰亚胺基苯酚广泛用作有机和医药中间体。

反应信息

• 作为反应物：
  描述：

  4-马来酰亚胺基苯酚 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.25h， 生成 4-(1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindol-2(3H)-yl)phenyl 4-(2,5-diethynyl-4-(4-(furan-2-ylmethoxy)-4-oxobutoxy)phenoxy)butanoate
  参考文献：
  名称：

  通过“点击”化学反应实现热可逆的Dendronized线性AB阶跃聚合物

  摘要：

  描述了热不稳定的树枝状线性AB阶跃聚合物的合成和表征。通过Cu（I）催化的叠氮化物-炔烃环加成反应，然后通过热可逆性呋喃-马来酰亚胺-Diels-Alder反应进行聚合，可制备出同时具有呋喃和呋喃保护的马来酰亚胺官能团的第一代至第三代树枝状AB单体14a - c。通过GPC研究了线性树枝状步长聚合物16a - c的组装，拆卸和重新组装行为。

  DOI：

  10.1021/ma200296t
• 作为产物：
  描述：

  [4-(2,5-二氧代吡咯-1-基)苯基]乙酸酯 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 硫酸 、 水 为溶剂， 以63%的产率得到4-马来酰亚胺基苯酚
  参考文献：
  名称：

  Process for the production of N-(hydroxyphenyl) maleimides

  摘要：

  通式为##STR1##的N-(羟基苯基)马来酰亚胺，其中R'代表H、CH.sub.3、C.sub.2 H.sub.5、F、Cl、Br或I，n为1-5的整数，通过处理相应的马来酰胺酸或在0-150°C温度下在至少选择自氧化硫或磷的氧化物和氧化酸以及所述氧化酸的碱金属和碱土金属盐中的一种脱水剂的存在下处理所述N-(羟基苯基)马来酰亚胺而制备得到。相应的马来酰胺酸可通过将在其苯环上具有一个或多个羟基基团的氨基酚与马来酸酐反应而获得。N-(羟基苯基马来酰亚胺)的酯可以通过在传统酸酐脱水剂和传统亚酰胺形成环化催化剂的存在下，使所述氨基酚和所述马来酸酐反应而获得。

  公开号：

  US04231934A1
• 作为试剂：
  描述：

  对氨基苯酚 、 马来酸酐 、 四磷十氧化物 、 N,N-二甲基甲酰胺 在 4-马来酰亚胺基苯酚 、 水 作用下， 以 水 为溶剂， 反应 4.5h， 以to obtain 25.1 g (0.133 moles) of N-(p-hydroxyphenyl) maleimide (yield 48.2%)的产率得到4-马来酰亚胺基苯酚
  参考文献：
  名称：

  Process for the production of N-(hydroxyphenyl) maleimides

  摘要：

  通式为##STR1##的N-(羟基苯基)马来酰亚胺，其中R'代表H、CH.sub.3、C.sub.2 H.sub.5、F、Cl、Br或I，n为1-5的整数，可通过处理相应的马来酰胺酸或处理该N-(羟基苯基)马来酰亚胺酯在0℃-150℃的温度下，在至少一种脱水剂的存在下制备，所述脱水剂选自氧化硫或磷的氧化物和氧酸盐以及所述氧酸盐的碱金属和碱土金属盐。相应的马来酰胺酸可通过将具有苯环上一个或多个羟基的氨基酚与马来酸酐反应而获得。该N-(羟基苯基马来酰亚胺)的酯可通过在常规酸酐脱水剂和常规亚胺形成环化催化剂的存在下，将所述氨基酚和所述马来酸酐反应而获得。

  公开号：

  US04289699A1

文献信息

• XANTHENE-BASED COMPOUND AND PHOTOSENSITIVE RESIN COMPOSITION COMPRISING SAME
  申请人：LG CHEM, LTD.

  公开号：US20200262807A1

  公开（公告）日：2020-08-20

  The present specification provides a compound represented by Chemical Formula 1, a colorant composition, a resin composition, a photosensitive material, a color filter and a display device comprising the same.

  当前规格书提供了一种由化学公式1表示的化合物，一种着色剂组合物，一种树脂组合物，一种光敏材料，以及包含该化合物的彩色滤光器和显示设备。
• Access to indoles<i>via</i>Diels-Alder reactions of 2-vinylpyrroles with maleimides
  作者：Wayland E. Noland、Nicholas P. Lanzatella、Lakshmanan Venkatraman、Nicholas F. Anderson、Glen C. Gullickson

  DOI：10.1002/jhet.198

  日期：2009.11

  Variously substituted 2‐vinylpyrroles underwent an endo‐addition [4+2] cycloaddition reaction with maleimides followed by a spontaneous highly diastereoselective (93–98% de) isomerization to give tetrahydroindoles in moderate to excellent yield. Treatment with activated MnO2 in refluxing toluene provided the corresponding indoles in moderate to good yield. This highly convergent methodology for formation

  各种取代的2-乙烯基吡咯与马来酰亚胺进行内加成[4 + 2]环加成反应，然后自发地高度非对映选择性（93-98％de）异构化，得到中等至优异收率的四氢吲哚。在回流的甲苯中用活化的MnO 2处理以中等至良好的产率提供了相应的吲哚。这种高度收敛的吲哚形成方法是通用的，并且可以方便地制备起始原料。J.杂环化​​学，（2009）。
• 一种含磷马来酰亚胺化合物及其制备方法
  申请人：南亚新材料科技股份有限公司

  公开号：CN110746458B

  公开（公告）日：2022-01-11

  本发明公开了一种含磷马来酰亚胺化合物，所述的含磷马来酰亚胺化合物化学结构式如式1所示：所述式1中的X如下式2‑1、2‑2或式3‑1、3‑2、3‑3、3‑4结构所示：所述式1中的Y如下式4‑1、式4‑2或式5‑1、5‑2结构所示：所述式1中的R如下式6‑1、式6‑2、式6‑3、式6‑4结构所示。本发明还公开了其制备方法。本发明将磷杂化型阻燃结构与马来酰亚胺基团结合，制备出一类含磷阻燃马来酰亚胺树脂，既能解决树脂阻燃、耐热性等固有难题，同时作为阻燃剂末端含有功能性的马来酰亚胺活性基团，作为反应性阻燃剂可以与其他树脂进行反应，提高阻燃剂与材料的相容性，并提升材料的热性能、介电性能等。
• Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions
  作者：Fabian Buller、Luca Mannocci、Yixin Zhang、Christoph E. Dumelin、Jörg Scheuermann、Dario Neri

  DOI：10.1016/j.bmcl.2008.07.038

  日期：2008.11

  DNA-encoded chemical libraries are increasingly being employed for the identification of binding molecules to protein targets of pharmaceutical relevance. Here, we describe the synthesis and characterization of a DNA-encoded chemical library, consisting of 4000 compounds generated by Diels-Alder cycloaddition reactions. The compounds were encoded with unique DNA fragments which were generated through

  DNA编码的化学文库正越来越多地用于鉴定与药物相关的蛋白质靶标的结合分子。在这里，我们描述了由Diels-Alder环加成反应生成的4000种化合物组成的DNA编码化学文库的合成和表征。这些化合物编码有独特的DNA片段，这些片段是通过逐步组装过程生成的，并用作可扩增的条形码，用于鉴定和相对定量文库成员。
• A facile and economical procedure for the synthesis of maleimide derivatives using an acidic ionic liquid as a catalyst
  作者：Kai Li、Chao Yuan、Shijun Zheng、Qiang Fang

  DOI：10.1016/j.tetlet.2012.06.025

  日期：2012.8

  in good yields and high purity from the corresponding maleamic acids using a Brønsted acidic room temperature ionic liquid (RTIL) as a catalyst. The products were obtained through merely a decanting and removal of the solvent, suggesting that this procedure is superior to the conventional routes, in which the strong organic/inorganic acids were used as the catalysts, as well as a complicated post-processing

  使用布朗斯台德酸性室温离子液体（RTIL）作为催化剂，从相应的马来酰胺酸中以高收率和高纯度合成了七个马来酰亚胺衍生物。仅通过de析和除去溶剂即可获得产物，这表明该方法优于常规方法，在常规方法中，使用强有机/无机酸作为催化剂，并且对烃类进行了复杂的后处理程序。使用产物的分离和纯化。

表征谱图