1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯 | 137814-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯
• 中文别名: 1,2-二(2-甲基苯并噻吩-3-基)-3,3,4,4,5,5-5氟-1-环戊烯；1,2-二[2-甲基苯并[B]硫代邻菲罗啉-3-基]-3,3,4,4,5,5-六氟-1-环戊烯；1,2-双[2-甲基苯并[b]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯
• 英文名称: 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene
• 英文别名: 1,2-bis(2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene；1,2-bis(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene；1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene；1,2-bis(2-methyl-1-benzothiophen-3-yl)hexafluorocyclopentene；1,2-bis(2-methyl-3-benzothienyl)perfluorocyclopentene；(3,3,4,4,5,5-hexafluorocyclopent-1-en-1,2-diyl)bis(2-methyl-1-benzothiophene)；3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(2-methylbenzo[b]thiophene)；1,2-bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclopentene；1,2-bis(2-methylbenzothiophen-3-yl)perfluorocyclopentene；1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene；3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-1-benzothiophen-3-yl)cyclopenten-1-yl]-2-methyl-1-benzothiophene
• CAS: 137814-07-4
• 化学式: C₂₃H₁₄F₆S₂
• mdl: MFCD06656279
• 分子量: 468.487
• InChiKey: CNLMHUFAXSWHFA-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 溶解度：
  略溶。在四氢呋喃中

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.217
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 储存条件：
  室温

SDS

1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-
hexafluoro-1-cyclopentene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION OF THE SUBSTANCE OR MIXTURE AND OF THE SUPPLIER
Product name: 1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
Not classified
PHYSICAL HAZARDS
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
None
Pictograms or hazard symbols
Signal word No signal word
Hazard statement None
Precautionary statements None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene
Component(s):
Percent: >97.0%(GC)
137814-07-4
CAS Number:
Chemical Formula: C23H14F6S2

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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.
Get medical advice/attention if you feel unwell. Rinse mouth.
Ingestion:
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Take care as it may decompose upon combustion or in high temperatures to
Specific hazards:
generate poisonous fume.
1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-
3,3,4,4,5,5-hexafluoro-1-cyclopentene

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

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
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
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.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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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
Solid
Physical state (20°C):
Form: crystal - powder
Color: White - Slightly pale yellow
Odor: No data available
pH: No data available
Melting point/freezing point:160 °C
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
Upper: No data available
Density: No data available
Solubility: Slightly soluble in: THF

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Stability:
Reactivity: No special reactivity has been reported.
Light-sensitive
Conditions to avoid:
1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-
3,3,4,4,5,5-hexafluoro-1-cyclopentene

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Section 10. STABILITY AND REACTIVITY
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride, Sulphur oxides
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:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
No data available
log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
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
Does not correspond to the classification standard of the United Nations
Hazards Class:
UN-No: Not Listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-
3,3,4,4,5,5-hexafluoro-1-cyclopentene

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯 在 sodium hydroxide 、 三氯化铝 、 氯化亚砜 、 高氯酸 、 thallium(III) nitrate 作用下， 以 1,4-二氧六环 、 乙醚 、 硝基苯 为溶剂， 反应 55.0h， 生成 1,2-bis<6-<<(diazomethyl)carbonyl>methyl>-2-methylbenzothiophen-3-yl>hexafluorocyclopentene
  参考文献：
  名称：

  Photochromic Diarylethenes with Intralocking Arms

  摘要：

  1,2-Bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with carboxyalkyl or alkyl mercaptan groups at 6 and 6' positions of the benzothiophene rings were synthesized with the aim of controlling the photochromic reactivity by external stimulation, such as chemicals or heat treatment. 1,2-Diarylethenes with heterocyclic five-membered rings have two atropisomers, and the photochromic reactivity depends on the conformation. When the molecule was fixed in a parallel conformation with intramolecular hydrogen bonds or an intramolecular disulfide linkage, the photochromic reactivity was completely inhibited. The molecule again became photoactive when the intramolecular lock was unclasped by the addition of hydrogen bond breaking or reducing agents. The diarylethene with carboxyethyl groups showed a thermal reaction threshold in decalin. At temperatures below 50 degrees C the molecule was photochemically inactive, while the photochromic property was recovered upon heating above 100 degrees C, at which temperatures the intramolecular hydrogen bonds are broken.

  DOI：

  10.1021/ja00101a010
• 作为产物：
  描述：

  苯并噻吩 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯
  参考文献：
  名称：

  光电聚合物材料：交联液晶聚合物与同构二芳烃的光响应行为

  摘要：

  制备了具有介晶二芳基乙烯的交联液晶（LC）聚合物，以证明将交联光致变色LC聚合物用作光移动材料的通用策略。暴露于紫外线下导致二芳基乙烯生色团发生光环化后，交联的聚合物薄膜会向光化光源弯曲。通过可见光照射，使闭环变成开环异构化，弯曲的薄膜恢复到初始的平坦状态。没有可见光照射，弯曲的薄膜甚至在120°C时仍保持弯曲，这表明交联的二芳基乙烯LC聚合物具有很高的热稳定性。

  DOI：

  10.1002/chem.201406299

文献信息

• A convenient method for the preparation of mono- and bis-substituted photochromic bis(benzothienyl)perfluorocyclopentenes via regioselective Friedel–Crafts acylation
  作者：A.M. Bogacheva、V.N. Yarovenko、K.S. Levchenko、O.I. Kobeleva、T.M. Valova、V.A. Barachevsky、M.I. Struchkova、P.S. Shmelin、M.M. Krayushkin、V.N. Charushin

  DOI：10.1016/j.tetlet.2012.08.111

  日期：2012.10

  The regioselective Friedel–Crafts acylation of 1,2-bis(2-methylbenzo[b]thien-3-yl)hexafluorocyclopentene was developed. Depending on the reaction conditions, mono- or bis(bromoacetyl) derivatives are formed as single products in good yields. Further heterocyclizations involving α-bromoketone moieties gave a series of new photochromic compounds.

  开发了区域选择性的1,2-双（2-甲基苯并[ b ]噻吩-3-基）六氟环戊烯的弗瑞德-克拉夫茨酰化反应。取决于反应条件，单-或双（溴乙酰基）衍生物以良好的产率形成为单一产物。涉及α-溴酮部分的进一步杂环化产生了一系列新的光致变色化合物。
• Novel saccharide tweezers with a diarylethene photoswitch
  作者：Michinori Takeshita、Kingo Uchida、Masahiro Irie

  DOI：10.1039/cc9960001807

  日期：——

  A photochromic saccharide receptor with a diarylethene photoswitch changes the binding event with glucose by photoirradiation.

  一种具有二芳基乙烯光开关的光变色糖类受体，通过光照改变与葡萄糖的结合事件。
• Photochromic properties of diarylethene derivatives having chryso[b]thiophene rings
  作者：Tadatsugu Yamaguchi、Yuji Fujita、Hiroyuki Nakazumi、Seiya Kobatake、Masahiro Irie

  DOI：10.1016/j.tet.2004.08.034

  日期：2004.10

  Diarylethene derivatives having one or two chryso[b]thiophene ring(s) have been synthesized. In solution the derivatives underwent photochromism and the derivative with one chryso[b]thiophene ring exhibited photochromism even in the single crystalline phase. The color of the UV irradiated single crystal changed from blue to green by rotation the sample under polarized light.

  已经合成了具有一个或两个Chryso [ b ]噻吩环的二芳基乙烯衍生物。在溶液中，衍生物经历了光致变色，并且具有一个金[ b ]噻吩环的衍生物甚至在单晶相中也表现出光致变色。通过在偏振光下旋转样品，被紫外线照射的单晶的颜色从蓝色变为绿色。
• A luminescent steroid-based organogel: ON–OFF photoswitching by dopant interplay and templated synthesis of fluorescent nanoparticles
  作者：Valeria C. Edelsztein、Elizabeth A. Jares-Erijman、Klaus Müllen、Pablo H. Di Chenna、Carla C. Spagnuolo

  DOI：10.1039/c2jm34891h

  日期：——

  The modulation of the fluorescence emission of a perylene dye between ON and OFF states was achieved with high efficiency by means of a diarylethene photochromic compound in an organogel medium. Fluorescent gels were prepared from a steroidal low molecular weight organogelator doped with the perylene fluorophore. The compatibility of the photochromic compound in this medium and the non-destructive readout capability were demonstrated. The dye doped organogel was further used as a template and an innovative method was employed to grow fluorescent silica spherical nanoparticles with physically and chemically admixed perylene dye.

  通过在有机胶体介质中使用二芳基乙烯光致变色化合物，实现了苝染料在开关状态之间的荧光发射调制，效率极高。荧光胶体是由掺杂苝荧光分子的类固醇低分子量有机胶体形成的。证明了光致变色化合物在该介质中的兼容性和非破坏性读取能力。掺染染料的有机胶体进一步作为模板，采用创新方法生长了物理和化学混合的荧光二氧化硅球形纳米颗粒。
• Photochromism of Bis(2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene Derivatives
  作者：Tadatsugu Yamaguchi、Masahiro Irie

  DOI：10.1021/jo051372z

  日期：2005.12.1

  Photochromic diarylethene derivatives having benzofuran heteroaryl groups, bis(2-methyl-1-benzofuran-3-yl)perfluorocyclopentene and bis(2-butyl-1-benzofuran-3-yl)perfluorocyclopentene, were synthesized, and their photochromic performance was examined in hexane solution as well as in the single-crystalline phase. The compounds exhibited photochromic reactivity even in the single-crystalline phase.

  合成了具有苯并呋喃杂芳基，双（2-甲基-1-苯并呋喃-3-基）全氟环戊烯和双（2-丁基-1-苯并呋喃-3-基）全氟环戊烯的光致变色二芳基乙烯衍生物，并对其光致变色性能进行了测试。己烷溶液以及在单晶相中。该化合物甚至在单晶相中也显示出光致变色反应性。