9-乙烯基蒽 | 2444-68-0

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-乙烯基蒽
• 中文别名: 9-乙烯蒽
• 英文名称: 9-vinylanthracene
• 英文别名: 9-Vinyl-anthracen；9-ethenylanthracene
• CAS: 2444-68-0
• 化学式: C₁₆H₁₂
• mdl: MFCD00003576
• 分子量: 204.271
• InChiKey: OGOYZCQQQFAGRI-UHFFFAOYSA-N

物化性质

• 熔点：
  62-65 °C (lit.)
• 沸点：
  61-66 °C/10 mmHg (lit.)
• 密度：
  1.1570 (estimate)
• 闪点：
  61-66°C/10mm
• 保留指数：
  311.6;311.7;334.13;334.63;336.76
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2902909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  请将容器密封，并将其存放在透气性好的储存器中，置于阴凉、干燥处保存。

SDS

Name:	9-Vinylanthracene Material Safety Data Sheet
Synonym:	Non
CAS:	2444-68-0

Section 1 - Chemical Product MSDS Name:9-Vinylanthracene Material Safety Data Sheet
Synonym:Non

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2444-68-0	9-Vinylanthracene	100.00	219-486-2

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
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.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. 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:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2444-68-0: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 61.0 - 66.0 deg C
Freezing/Melting Point: 64.00 - 66.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C16H12
Molecular Weight: 204.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2444-68-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
9-Vinylanthracene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 2444-68-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2444-68-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2444-68-0 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

制备方法

2-8℃储存。

用途简介

暂无内容。

用途

2-8℃储存。

反应信息

• 作为反应物：
  描述：

  9-乙烯基蒽 在 aluminum oxide 、 potassium permanganate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以98%的产率得到蒽醌
  参考文献：
  名称：

  苯乙烯和肉桂酸衍生物的多相高锰酸盐氧化：一种简单有效的苯甲醛制备方法

  摘要：

  当在非均相条件下被高锰酸盐氧化时，苯乙烯和肉桂酸衍生物产生相应取代的苯甲醛。末端脂肪烯烃在相似条件下的反应产率低得令人沮丧。然而，酮和酮醇分别通过 2,2-二取代和三取代烯烃的氧化以非常好的收率获得。氧化铝和 Amberlite IR-120 可用作这些反应中的固体支持物，具有同样良好的效果。

  DOI：

  10.1055/s-2001-16760
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium hydrogensulfate 作用下， 生成 9-乙烯基蒽
  参考文献：
  名称：

  Sianesi, Gazzetta Chimica Italiana, 1959, vol. 89, p. 1749,1759

  摘要：

  DOI：

文献信息

• N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions
  作者：Dan Li、Qingqiang Tian、Xuetong Wang、Qiang Wang、Yin Wang、Siwei Liao、Ping Xu、Xin Huang、Jianyong Yuan

  DOI：10.1080/00397911.2021.1919711

  日期：——

  Abstract A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products

  摘要 报道了一种温和、高效且实用的催化系统，用于合成高度特权的二苯乙烯药效团。该系统使用N-杂环卡宾钯(II)吡啶(NHC-Pd(II)-Py)配合物催化烯烃衍生物与各种溴化物之间形成碳-碳键。这种简单、温和且用户友好的方法可以在无溶剂条件下以优异的收率提供各种二苯乙烯产品。且其放大反应收率优良，可应用于工业领域。该方法的实用性突出表现在其可合成一系列生物活性分子或重要的医药中间体的通用性和模块化合成。
• Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
  作者：Xiaofang Gao、Xiaojun Pan、Jian Gao、Huawen Huang、Gaoqing Yuan、Yingwei Li

  DOI：10.1039/c4cc07606k

  日期：——

  A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group tolerance. The reaction mechanism was revealed to proceed through a domino reaction of oxidation and elimination after the radical addition to alkenes

  描述了一种新型的碘化铵诱导的烯烃与DMSO和水的磺酰化反应，以合成乙烯基甲基砜。该过程在无金属条件下顺利进行，具有高立体选择性和良好的官能团耐受性。在自由基加成到烯烃上之后，揭示了反应机理是通过氧化和消除的多米诺反应进行的。
• “Bulky-Yet-Flexible” α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
  作者：Xu-Wen Yang、Dong-Hui Li、A-Xiang Song、Feng-Shou Liu

  DOI：10.1021/acs.joc.0c01509

  日期：2020.9.18

  regioselective and efficient reductive Heck reaction, a series of moisture- and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the“bulky-yet-flexible”palladium complexes allowed highly anti-Markovnikov-selective

  为了进行高度区域选择性和高效的还原性Heck反应，合理设计，易于合成和充分表征了一系列湿气和空气稳定的α-二亚胺钯预催化剂。研究了钯配合物的结构与催化性能之间的关系。揭示了“大而尚柔的”钯配合物在好氧条件下可以使烯烃与（杂）芳基溴化物高度抗马尔科夫尼科夫选择性加氢芳基化。本方案的进一步合成应用可以提供对功能和生物活性分子的快速直接访问。
• Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent
  作者：Dodla S. Rao、Thurpu R. Reddy、Aakanksha Gurawa、Manoj Kumar、Sudhir Kashyap

  DOI：10.1021/acs.orglett.9b03910

  日期：2019.12.20

  Photoswitchable strategy for selective azidation of structurally diverse olefins under transition-metal-free conditions is reported. The unprecedented reactivity of trimethylsulfonium [bis(azido)iodate(I)] species under visible light allows radical azidooxygenation of the C═C π bond with distinctive selectivity. In the absence of visible light, the reaction proceeds through an ionic intermediate which

  据报道，在无过渡金属条件下，采用光开关策略可选择性叠氮化结构多样的烯烃。三甲基ulf [双（叠氮基碘酸盐）（I）]在可见光下具有空前的反应性，可实现C═Cπ键的自由基叠氮加氧，并具有独特的选择性。在不存在可见光的情况下，反应通过离子中间体进行，该离子中间体导致互补的区域选择性以提供α-烷基叠氮化物。机理研究表明，涉及自由基或离子途径的光控区域发散叠氮化可以通过唯一的区域选择性来实现。
• Birch‐Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
  作者：Anamitra Chatterjee、Burkhard König

  DOI：10.1002/anie.201905485

  日期：2019.10

  energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

  通过可见光照射直接还原芳烃和杂芳烃仍然具有挑战性，因为单个光子的能量不足以破坏芳香族的稳定性。本文显示两个可见光光子的能量积累允许芳烃和杂芳烃的脱芳构化。机理研究证实，能量转移和电子转移过程的结合产生芳烃自由基阴离子，随后被氢原子转移捕获，最后质子化形成脱芳构化产物。光还原将平面芳香族原料化合物转化为可用于有机合成的分子骨架。

表征谱图