tetraphenylene | 212-74-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: tetraphenylene
• 英文别名: (4aZ,8aZ,12aZ,16aZ)-tetraphenylene
• CAS: 212-74-8
• 化学式: C₂₄H₁₆
• 分子量: 304.391
• InChiKey: KTQYWNARBMKMCX-LEYBOLSUSA-N

物化性质

• 熔点：
  232-235 °C(lit.)
• 沸点：
  380.21°C (rough estimate)
• 密度：
  1.1440 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• 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

SDS

Name:	Tetraphenylene 98% Material Safety Data Sheet
Synonym:	Tetrabenzo[a,c,e,g]cyclooctatetraen
CAS:	212-74-8

Section 1 - Chemical Product MSDS Name:Tetraphenylene 98% Material Safety Data Sheet
Synonym:Tetrabenzo[a,c,e,g]cyclooctatetraen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
212-74-8	Tetraphenylene	98	unlisted

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: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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:
Wash area with soap and water. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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. 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 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# 212-74-8: Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: Crystals
Color: light yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 229.00 - 231.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C24H16
Molecular Weight: 304.39

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 212-74-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tetraphenylene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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.
WGK (Water Danger/Protection)
CAS# 212-74-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 212-74-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 212-74-8 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

反应信息

• 作为反应物：
  描述：

  tetraphenylene 生成 9,10-苯并菲
  参考文献：
  名称：

  To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene

  摘要：

  Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of enantiopure 7 showed that the molecule retained its chirality integrity during its synthesis from enantiopure precursors and therefore rules out the possibility of the tetraphenylene framework possessing a low-energy barrier to inversion. Thermal study on 15 and tetraphenylene I further revealed that their inversion barriers were not overcome up to 600 degrees C, at which temperature these compounds underwent skeletal contraction into triphenylene with activation energies of 62.8 and 58.2 kcal/mol, respectively. This result is supported by computational studies which yielded an inversion barrier of 135 kcal/mol for tetraphenylene as a consequence of the peri-hydrogen repulsions at its planar conformation.

  DOI：

  10.1021/jo802061p
• 作为产物：
  描述：

  2-碘联苯 在 1-溴-2-萘酚 、 palladium diacetate 、 2Li⁽¹⁺⁾*CO₃^(2-)*HLi 、 cesium pivalate 、 三(4-氟苯基)磷化氢 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以45%的产率得到tetraphenylene
  参考文献：
  名称：

  通过Pd（0）催化邻碘联芳基与溴酚的螺环化芴基螺环的二合一策略

  摘要：

  芴基螺环的快速组装代表了有机合成中非常重要但具有挑战性的任务。本文报道的是一种新颖的Pd（0）催化的简单邻碘二芳基与溴酚合成的Pd（0）螺环化，用于一步合成高纯度[4,5]-螺芴并具有出色的官能团耐受性。值得注意的是，这些有价值的芴基香豆素骨架可以丰富C-香豆素的数据库，并具有出色的光谱性能。

  DOI：

  10.1039/d0sc04386a

文献信息

• An Approach to Tetraphenylenes via Pd-Catalyzed C–H Functionalization
  作者：Hang Jiang、Yu Zhang、Dushen Chen、Bo Zhou、Yanghui Zhang

  DOI：10.1021/acs.orglett.6b00641

  日期：2016.5.6

  asymmetric catalysis. A facile and efficient approach is reported for the syntheis of tetraphenylene and its derivatives from 2-iodobiphenyls via Pd-catalyzed C–H activation. A range of substituted tetraphenylenes can be synthesized using this method, and the reaction can be performed on gram scale with relatively high efficiency, demonstrating its practical utility. This novel approach provides easy access

  四亚苯基不仅在理论上和实验上令人关注，而且在材料科学，超分子化学和不对称催化等许多领域中都有潜在的应用。据报道，一种简便有效的方法是通过Pd催化的C–H活化从2-碘代联苯合成四联苯及其衍生物。使用该方法可以合成许多取代的四亚苯基，并且该反应可以以相对较高的效率以克为单位进行，这证明了其实用性。这种新颖的方法提供了容易获得的四亚苯基，并应促进对这种迷人分子的应用的研究。
• Mechanistic Investigation of Catalytic Carbon−Carbon Bond Activation and Formation by Platinum and Palladium Phosphine Complexes
  作者：Brian L. Edelbach、Rene J. Lachicotte、William D. Jones

  DOI：10.1021/ja973368d

  日期：1998.4.1

  The complexes Pt(PEt3)3 and Pd(PEt3)3 cleave the C−C bond of biphenylene to give (PEt3)2Pt(2,2‘-biphenyl), 1, and (PEt3)2Pd(2,2‘-biphenyl), respectively. Heating (PEt3)2Pt(2,2‘-biphenyl) in the presence of biphenylene leads to C−C cleavage of a second biphenylene to give (PEt3)2Pt(2,2‘-tetraphenyl), 2, via a Pt(IV) intermediate. 2 reductively eliminates tetraphenylene at 115 °C. At 120 °C the reaction

  配合物 Pt(PEt3)3 和 Pd(PEt3)3 裂解联苯的 C-C 键，得到 (PEt3)2Pt(2,2'-联苯), 1, 和 (PEt3)2Pd(2,2'-联苯) ）， 分别。在亚联苯存在下加热 (PEt3)2Pt(2,2'-联苯) 导致第二个亚联苯的 C-C 裂解得到 (PEt3)2Pt(2,2'-四苯基), 2，通过 Pt(IV) ） 中间的。2 在 115 °C 时还原消除四亚苯基。在 120 °C 时，反应是催化的；Pt(PEt3)3 或 1 将亚联苯转化为四亚苯基。催化循环中的中间体已被鉴定，1 和 2 已通过 X 射线分析表征。在催化条件下，1 和 2 接近稳态浓度。动力学分析表明，稳态浓度比、静止状态种类和总催化速率 kobs 取决于联苯与 PEt3 的比率。
• Oxidative Homocoupling Reaction of Aryltrimethylsilanes by Pd/<i>o</i>-Chloranil Catalysis
  作者：Mari Shibata、Hideto Ito、Kenichiro Itami

  DOI：10.1246/cl.170723

  日期：2017.12.5

  oxidative homocoupling reaction of aryltrimethylsilanes has been achieved by Pd/o-chloranil catalytic system. The reaction shows the good functional group tolerability toward bromo, fluoro, ester, and methoxy groups to give a series of biaryls bearing electron-withdrawing and -donating groups. The boronate group is also retained on biaryls without any Ar–B bond cleavage, which is highly advantageous for

  Pd/o-氯苯醌催化体系实现了芳基三甲基硅烷的实际氧化均偶联反应。该反应显示出对溴、氟、酯和甲氧基的良好官能团耐受性，得到一系列带有吸电子和供电子基团的联芳基。硼酸酯基团也保留在联芳基上，没有任何 Ar-B 键断裂，这对于正交耦合非常有利。
• 含四邻亚苯基配体的有机发光材料
  申请人：北京夏禾科技有限公司

  公开号：CN109575085B

  公开（公告）日：2021-11-23

  公开了一种含四邻亚苯基配体的有机发光材料,其通过提供一种金属络合物来实现，采用了一系列新的包括含四邻亚苯结构的配体。这些新颖配体的使用能够降低固态时的聚集，提高器件寿命。还公开了一种电致发光器件和化合物配方。
• Carbon–Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes
  作者：James R. Bour、Nicole M. Camasso、Elizabeth A. Meucci、Jeff W. Kampf、Allan J. Canty、Melanie S. Sanford

  DOI：10.1021/jacs.6b10350

  日期：2016.12.14

  This manuscript describes the design, synthesis, characterization, and reactivity studies of organometallic NiIII complexes of general structure TpNiIII(R)(R1) (Tp = tris(pyrazolyl)borate). With appropriate selection of the R and R1 ligands, the complexes are stable at room temperature and can be characterized by cyclic voltammetry, EPR spectroscopy, and X-ray crystallography. Upon heating, many of

  本手稿描述了一般结构 TpNiIII(R)(R1)（Tp = 三（吡唑基）硼酸盐）的有机金属 NiIII 配合物的设计、合成、表征和反应性研究。With appropriate selection of the R and R1 ligands, the complexes are stable at room temperature and can be characterized by cyclic voltammetry, EPR spectroscopy, and X-ray crystallography. 加热后，许多这些 NiIII 化合物会发生 C(sp2)-C(sp2) 或 C(sp3)-C(sp2) 键形成反应，这些反应在镍的较低氧化态下具有挑战性。

表征谱图