1,4,5,8-萘四甲酸酐 | 81-30-1

• 物质功能分类: 化学试剂 - 有机试剂 - 双环化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 中文名称: 1,4,5,8-萘四甲酸酐
• 中文别名: 1,4,5,8-萘四酸二酐；萘-1,4,5,8-四羧酸二酐；萘-1,4,5,8-四甲酸二酐；LT-S924
• 英文名称: 1,4,5,8-naphthalenetetracarboxylic dianhydride
• 英文别名: naphthalene-1,8:4,5-tetracarboxylic dianhydride；naphthalene-1,4,5,8-tetracarboxylic dianhydride；1,4,5,8-naphthalenetetracarboxylic acid dianhydride；NTCDA；naphthalene dianhydride；naphthalene-1,4,5,8-tetracarboxylic acid dianhydride；naphthalene-1,4,5,8-tetracarboxylic acid anhydride；1,4,5,8-naphthalene tetracarboxylic anhydride；naphthalenetetracarboxylic dianhydride；NDA；6,13-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 81-30-1
• 化学式: C₁₄H₄O₆
• mdl: MFCD00006915
• 分子量: 268.182
• InChiKey: YTVNOVQHSGMMOV-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (lit.)
• 沸点：
  371.34°C (rough estimate)
• 密度：
  1.5122 (rough estimate)
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  29173990
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  QK3695000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  本品应密封存于干燥避光处。1,4,5,8-萘四甲酸酐(1,4,5,8-萘四甲酸二酐)应贮存在阴凉、干燥的环境中，以防受潮。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,4,5,8-Naphthalenetetracarboxylic dianhydride, tech grade
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 1,4,5,8-Naphthalenetetracarboxylic dianhydride, tech grade
CAS number: 81-30-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H4O6
Molecular weight: 268.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用1,4,5,8-萘四甲酸酐可以作为化工医药中间体，在实验室研发和化工医药合成过程中具有重要作用。

反应信息

• 作为反应物：
  描述：

  1,4,5,8-萘四甲酸酐 在 ammonium hydroxide 作用下， 反应 24.0h， 以87%的产率得到1,4,5,8-萘四甲酰基二酰亚胺
  参考文献：
  名称：

  萘二酰亚胺的还原性芳构化：2,7-二氮杂戊烯的多功能平台†

  摘要：

  萘二酰亚胺的还原芳构化提供了四新戊氧基-2,7-二氮杂py，这是通向外围取代的2,7-二氮杂戊烯的通用平台。时间分辨的微波电导率测量表明，2,7-二氮杂ne的固有电子迁移率显着高于相应的pyr。

  DOI：

  10.1039/c8cc01937a
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 1,4,5,8-萘四甲酸酐
  参考文献：
  名称：

  METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE, METHOD FOR PRODUCING CARBOXYLIC IMIDE, AND METHOD FOR MANUFACTURING ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER

  摘要：

  生产羧酸酐的方法包括加热含有特定化合物的溶剂中的混合物，以产生羧酸酐。该溶剂是具有沸点为50°C或更高的无水极性溶剂。

  公开号：

  US20160376285A1

文献信息

• Supramolecularly Engineered Amphiphilic Macromolecules: Molecular Interaction Overrules Packing Parameters
  作者：Prithankar Pramanik、Debes Ray、Vinod K. Aswal、Suhrit Ghosh

  DOI：10.1002/anie.201611715

  日期：2017.3.20

  P2‐50 adopted self‐sorted assembly. For either series of polymers, variation in the hydrophobic/hydrophilic balance does not alter the morphology reconfirming that self‐assembly is primarily driven by directional molecular interaction which is capable of overruling the existing norms in packing parameter‐dependent morphology control in an immiscibility‐driven block copolymer assembly.

  我们报告了由分子相互作用驱动的超分子工程两亲大分子（SEAM）的自组装，该分子包含一个超分子结构定向单元（SSDU），该单元由与萘二酰亚胺发色团连接的H键合基团组成。由于H键合基团（酰肼或H键）的不同，两种具有相同化学结构和疏水/亲水平衡的SEAM P1-50和P2-50表现出不同的自组装结构（分别为聚合物小体和圆柱形胶束）。单个SSDU的酰胺）。当混合在一起时，P1-50和P2-50采用自分类组装。对于任一系列的聚合物，
• Anion interaction with homoditopic chlorodiorganotin(IV) dithiocarbamate complexes derived from a naphthalene diimide. A pathway to obtain metallomacrocycles
  作者：Nadia Alejandra Rodríguez-Uribe、Miguel Ángel Claudio-Catalán、Felipe Medrano、Georgina Pina Luis、Hugo Tlahuext、Carolina Godoy-Alcántar

  DOI：10.1016/j.poly.2020.114615

  日期：2020.8

  triorganotin(IV) dithiocarbamate] complexes derived from naphthalene diimide (NDI) with general formula NDI-[(CH2)2-N(CH2Ph)(CS2SnR2X)]2, 3: R = n-Bu, X = Cl; 4: R = Me, X = Cl; 5: R = Ph, X = Cl; 6: R = X = Me; were prepared from triethylammonium ((1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis(ethane-2,1-diyl))bis(benzylcarbamodithioate) 2. All compounds were characterized

  摘要从萘二酰亚胺（NDI）衍生出通式为NDI-[（CH2）2-N（ Ph）（CS2SnR2X）] 2，3：R =的四种新的同位双双[氯二有机锡（IV）和三有机锡（IV）二硫代氨基甲酸酯]配合物n-Bu，X = Cl；4：R =我，X = Cl；5：R = Ph，X = Cl；6：R = X = Me；由三乙基铵（（（1,3,6,8-tetraoxo-1,3,6,8-四氢苯并[lmn] [3,8]菲咯啉-2,7-二基）双（乙烷-2,1-二基））双（苄基氨基甲酸二硫酯）2.所有化合物均通过IR以及1H和13C NMR光谱进行表征。配合物3–6也通过119Sn NMR光谱进行了表征。另外，通过单晶X射线衍射分析进一步表征复合物3。对配合物3进行的晶体学研究表明，锡原子的配位几何形状介于正方形金字塔和三角双锥体之间，τ值为0.69。另外观察到在3的晶体结构中存在协作的CH…π，CH…S，CH…O和S…π分子内相互作用。通过UV
• Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
  作者：Colleen P. Chernowsky、Alyah F. Chmiel、Zachary K. Wickens

  DOI：10.1002/anie.202107169

  日期：2021.9.20

  Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)−N and C(sp2)−O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe

  在此，我们公开了电化学刺激从一系列结构多样的传统光催化剂中诱导出新的光催化活性。这些研究揭示了一种新型电子引发的光氧化还原催化剂，能够促进强 C(sp 2 )−N 和 C(sp 2 )−O 键的还原裂解。我们举例说明了这些深度还原但安全且温和的催化条件的合成用途。最后，我们采用电化学电流测量来进行反应进程动力学分析。该技术表明，该新系统的活性提高是催化剂稳定性增强的结果。
• Quinoidization of π‐Expanded Aromatic Diimides: Photophysics, Aromaticity, and Stability of the Novel Quinoidal Acenes
  作者：Nareshbabu Kamatham、Jingbai Li、Siamak Shokri、Guang Yang、Steffen Jockusch、Andrey Yu. Rogachev、A. Jean‐Luc Ayitou

  DOI：10.1002/ejoc.201901456

  日期：2020.2.28

  Quinoidization of polyaromatic acenes, mediated by the Lawesson reagent, was implemented to afford novel quinoidal triplet chromophores. The photophysical properties of the synthesized compounds were studied.

  通过Lawesson试剂介导的聚芳烃并苯醌的喹啉化反应可提供新颖的喹啉三联体生色团。研究了合成化合物的光物理性质。
• Glycoluril‐Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water
  作者：Nengfang She、Damien Moncelet、Laura Gilberg、Xiaoyong Lu、Vladimir Sindelar、Volker Briken、Lyle Isaacs

  DOI：10.1002/chem.201601796

  日期：2016.10.17

  Molecular clip 1 remains monomeric in water and engages in host–guest recognition processes with suitable guests. We report the Ka values for 32 1⋅guest complexes measured by 1H NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that

  分子夹1在水中仍然是单体，并与合适的客人一起参与宿主-客体识别过程。我们报告了通过1 H NMR，UV / Vis和荧光滴定法测得的32个1⋅客体配合物的K a值。1的腔体由负电势的芳族表面形成，因此对平面和阳离子芳族客体显示出高亲和力和选择性，这使其与CB [ n ]受体相区别，后者比脂族客体更喜欢脂肪族。静电作用在识别过程中起着主要作用，在此过程中，铵离子和C = O的1个基团之间可能发生离子-偶极相互作用。情况下，SO之间3 -基团的1和在来宾悬垂阳离子基团，和空腔内1由阳离子-π相互作用。宿主1对具有大的平面芳族表面（例如萘二酰亚胺NDI +和per二酰亚胺PDI +）和衍生自a啶的阳离子染料（例如亚甲基蓝和天蓝色A）表现出较高的亲和力。通过比较类似的中性和阳离子客体（例如，亚甲基紫与亚甲基蓝；喹啉与N-甲基喹啉鎓； a啶与N-甲基ac啶；中性红与中性红H +）可以确定阳离子-π相

表征谱图