反,反-1,4-均二苯乙烯 | 1608-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 反,反-1,4-均二苯乙烯
• 中文别名: trans,trans-1,4-均二苯乙烯；1,4-双(反-2-苯基乙基)苯；1,4-双(反-2-苯基乙基)苯,97%
• 英文名称: 1,4-Distyrylbenzene
• 英文别名: 1,4-Bis[(E)-2-phenylethenyl]benzene
• CAS: 1608-41-9
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: IJAAWBHHXIWAHM-PHEQNACWSA-N

物化性质

• 熔点：
  264-266℃
• 沸点：
  443.6±30.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  356nm(Benzene)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  4
• 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

• 储存条件：
  室温

SDS

trans,trans-1,4-Distyrylbenzene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: trans,trans-1,4-Distyrylbenzene

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: trans,trans-1,4-Distyrylbenzene
Percent: >98.0%(GC)
CAS Number: 1608-41-9
Chemical Formula: C22H18

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
trans,trans-1,4-Distyrylbenzene

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Section 5. FIRE-FIGHTING MEASURES
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: Very pale yellow - Pale yellow green
Odour: No data available
pH: No data available
Melting point/freezing point:266°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
trans,trans-1,4-Distyrylbenzene

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Section 10. STABILITY AND REACTIVITY
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
trans,trans-1,4-Distyrylbenzene

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  反,反-1,4-均二苯乙烯 在 碘 、 二甲基亚砜 作用下， 反应 20.0h， 以86%的产率得到乙二酮,苯基[4-[(1E)-2-苯基乙烯基]苯基]-
  参考文献：
  名称：

  Iodine in Dimethyl Sulfoxide as a New General Reagent for the Preparative Oxidation of 1,2-Diarylethenes and 1,2-Diarylethynes to Aromatic 1,2-Diketones

  摘要：

  DOI：

  10.1055/s-1991-26397
• 作为产物：
  描述：

  四乙基-1,4-苯二膦酸酯 在 palladium diacetate 三甲基溴硅烷 、 十二/十四烷基二甲基氧化胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 29.5h， 生成 反,反-1,4-均二苯乙烯
  参考文献：
  名称：

  涉及芳基膦酸碳-磷键断裂的氧化 Heck 型反应

  摘要：

  碳-磷键的裂解是在钯催化下在利用芳基膦酸的氧化 Heck 型反应中实现的。芳基膦酸与烯烃的反应在三甲胺氧化物作为氧化剂的 TBAF 存在下以良好的收率提供芳基化产物。

  DOI：

  10.1021/ja026758v

文献信息

• Facile Regio- and Stereoselective Hydrometalation of Alkynes with a Combination of Carboxylic Acids and Group 10 Transition Metal Complexes: Selective Hydrogenation of Alkynes with Formic Acid
  作者：Ruwei Shen、Tieqiao Chen、Yalei Zhao、Renhua Qiu、Yongbo Zhou、Shuangfeng Yin、Xiangbo Wang、Midori Goto、Li-Biao Han

  DOI：10.1021/ja2069246

  日期：2011.10.26

  highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt(3))(4) (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a

  通过炔烃、羧酸和零价族 10 过渡金属络合物 M(PEt(3))(4) (M =镍、钯、铂）。一项机理研究表明，氢金属化不是通过炔烃与由羧酸与 Pt(PEt(3))(4) 质子化产生的氢化金属反应进行的，而是通过炔烃配位金属络合物与酸。这一发现阐明了长期以来提出的反应机制，该机制通过生成烯基钯中间体和随后在由 Brφnsted 酸和 Pd(0) 配合物的组合催化的各种反应中转化该配合物来进行。
• Palladium-Catalyzed Reductive Coupling Reaction of Terminal Alkynes with Aryl Iodides Utilizing Hafnocene Difluoride as a Hafnium Hydride Precursor Leading to <i>trans</i> -Alkenes
  作者：Keita Takahashi、Yohei Ogiwara、Norio Sakai

  DOI：10.1002/asia.201701775

  日期：2018.4.4

  Herein, we describe a reductive cross‐coupling of alkynes and aryl iodides by using a novel catalytic system composed of a catalytic amount of palladium dichloride and a promoter precursor, hafnocene difluoride (Cp2HfF2, Cp=cyclopentadienyl anion), in the presence of a mild reducing reagent, a hydrosilane, leading to a one‐pot preparation of trans‐alkenes. In this process, a series of coupling reactions

  在本文中，我们描述了通过使用新型催化体系（包括催化量的二氯化钯和助催化剂前体二茂fluor二氟化物（Cp 2 HfF 2，Cp =环戊二烯基阴离子）组成的炔烃和碘代芳烃的还原性交叉偶联。一种温和的还原剂，氢硅烷，可以一锅制备反式烯烃。在此过程中，一系列的偶联反应通过以下三个步骤有效地进行：（i）由二茂ha和氢硅烷初步形成initial氢化物，（ii）随后向炔烃加氢卤化，以及（iii）烯基ha物种变成钯络合物。该还原偶联可化学选择用于制备具有各种官能团（例如烷基，卤素，酯，硝基，杂环，硼酸酯和内部炔烃）的反式烯烃。
• Fulvenes and thermochromic ethylenes. Part LXXXIII. ‘Double dibenzotropones’ within C₆-C₇-C₆-C₇-C₆ring systems. Synthesis of bisbenzo[4,5]cyclohepta[1,2-a:2′,1′-d]benzene-5,7-dione and bisbenzo-[4,5]cyclohepta[1,2-a:1′,2′-d]benzene-5,13-dione
  作者：Israel Agranat、David Avnir

  DOI：10.1039/p19740001155

  日期：——

  Condensation of pyromellitic anhydride with phenylacetic acid (2 mol. equiv.) gave the two isomeric di-γ-lactones of 4,6-bis-(α-hydroxystyryl)isophthalic acid (IX) and 2,5-bis-(α-hydroxystyryl)terephthalic acid (X) in the ratio of 5:3. 4,6-Bis-(2-phenylethyl)isophthalic acid (XI) and 2,5-bis-(2-phenylethyl)terephthalic acid (XIII), formed by reduction of (IX) and (X), respectively, have been cyclized

  与苯乙酸苯均四酸酐的缩合（2摩尔当量），得到两种异构体的二γ内酯的4,6-双- （α-羟基苯乙烯基）间苯二甲酸（IX）和2,5-二- （α-羟基苯乙烯基）对苯二甲酸（X）的比例为5：3。通过还原（IX）和（X）分别形成的4，6-双（2-苯基乙基）对苯二甲酸（XI）和2，5-双-（2-苯基乙基）对苯二甲酸（XIII）已经被开发。环化和脱氢为双苯并[4,5]-环庚[1,2- a：2'，1' - d ]苯-5,7-二酮（III）和双苯并[4,5]环庚[1,2- a：1'，2' - d ]苯-5，13-二酮（IV）。
• Palladium-Catalyzed Stereoselective Synthesis of (E)-Stilbenes via Organozinc Reagents and Carbonyl Compounds
  作者：Jin-Xian Wang、Kehu Wang、Lianbiao Zhao、Hongxia Li、Ying Fu、Yulai Hu

  DOI：10.1002/adsc.200606016

  日期：——

  In the presence of a catalytic amount of PdCl2(PPh3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.

  在催化量的PdCl 2（PPh 3）2和甲硅烷基化剂的存在下，有机锌卤化物与羰基化合物反应，在温和的条件下以良好或优异的收率得到相应的（E）-芪。简要讨论了反应机理。
• Phenylenevinylene oligomers by Mizoroki-Heck cross coupling reaction. Structural and optoelectronic characterization
  作者：Sandra E. Estrada、Cristian Ochoa-Puentes、Cesar A. Sierra

  DOI：10.1016/j.molstruc.2016.12.032

  日期：2017.4

  spectroscopies. The results showed that, with only one exception, the ED and EW groups at the ends of OPV systems lead to a bathochromic shift. This effect is intensified with the introduction of methoxy groups on the central ring. Consistent with these, the HOMO-LUMO gaps (ΔE) decreases as the strength of ED and EW substituents increases. The ED and EW substituents also lead to a decrease in the Φ f values

  摘要 为了研究分子结构对全反式亚苯基亚乙烯基低聚物 (OPV) 光学性质的影响，16 种 1,4-二苯乙烯基苯衍生物（ 1a-i 和 2a-g ）具有不同的给电子（ED）功能。 ) 和吸电子 (EW) 基团通过 Mizoroki-Heck 交叉偶联反应以中等至良好的产率（40-95%）合成。所实施的方法，经过我们小组先前报道的小改动，可以获得所需的乙烯基构型以及一种新型 OPV 化合物 (1h)。在通过几种技术（例如 FTIR、 1 H、 13 C 和固态核磁共振）进行结构表征后，特别强调通过紫外-可见光和荧光光谱研究它们的光学特性。结果表明，除了一个例外，OPV 系统末端的 ED 和 EW 组导致红移。随着在中心环上引入甲氧基，这种效果得到加强。与这些一致，HOMO-LUMO 间隙（ΔE）随着 ED 和 EW 取代基强度的增加而减小。ED 和 EW 取代基也会导致 Φ f 值降低。这种在

表征谱图