2-溴-3-癸基噻吩 | 144012-09-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-溴-3-癸基噻吩
• 英文名称: 2-bromo-3-decylthiophene
• CAS: 144012-09-9
• 化学式: C₁₄H₂₃BrS
• 分子量: 303.307
• InChiKey: YCWPDFSNGOICAB-UHFFFAOYSA-N

物化性质

• 沸点：
  339.6±22.0 °C(Predicted)
• 密度：
  1.11g/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

2-Bromo-3-decylthiophene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2-Bromo-3-decylthiophene

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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: 2-Bromo-3-decylthiophene
Percent: >97.0%(GC)
CAS Number: 144012-09-9
Chemical Formula: C14H23BrS

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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:
Unsuitable extinguishing Solid streams of water
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
2-Bromo-3-decylthiophene

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Section 5. FIRE-FIGHTING MEASURES
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.
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 Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

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

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
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): Liquid
Form: Clear
Colorless - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
Relative density: 1.16
Solubility(ies):
2-Bromo-3-decylthiophene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Sulfur oxides, Hydrogen bromide
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:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
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 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
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
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
2-Bromo-3-decylthiophene

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴-3-癸基噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,5-bis(3-decylthiophen-2-yl)thiazolo[5,4-d]thiazole
  参考文献：
  名称：

  具有萘[1,2- b：5,6 - b' ]二噻吩核的晶体D-π-A有机小分子，用于溶液处理的有机太阳能电池

  摘要：

  在这项工作中，我们设计并合成了一种新的含有萘并[1,2- b：5,6- b' ]二噻吩的扩大π共轭供体-受体（D-A）小分子NDT（TTz）2，用于溶液处理的有机光伏。通过顺序的Suzuki和Stille合成了NDT（TTz）2，其中NDT（TTz）2包含噻吩桥接的萘并[1,2- b：5,6 - b' ]二噻吩作为中心稠合核心，三苯胺侧翼噻吩噻唑并噻唑作为间隔基偶联反应。NDT（TTz）2的热，物理化学和电化学性质已通过差示扫描量热法，热重分析法，紫外可见光谱，光致发光光谱，X射线衍射和循环伏安法进行了评估。如光伏应用所希望的那样，NDT（TTz）2具有良好的溶解性，热稳定性和井井有条的π-π堆叠结晶性。NDT（TTz）2的光学带隙和HOMO能级分别确定为2.0 eV和-5.23 eV。除了研究有机薄膜晶体管外，还通过与PC 71一起制造溶液处理的体异质结太阳能电池，研究了NDT（TTz）

  DOI：

  10.1016/j.orgel.2012.09.019
• 作为产物：
  描述：

  癸基溴 在 N-溴代丁二酰亚胺(NBS) 、 magnesium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-溴-3-癸基噻吩
  参考文献：
  名称：

  Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers

  摘要：

  我们展示了通过Suzuki同聚合反应，利用双(频哪醇基)二硼直接聚合对称、双溴、噻吩基单体，以较少步骤形成共聚物的方法。通过采用两种方法（新方法和常用的Stille共聚法）制备四种噻吩基共聚物，并将这种方法与Stille共聚法进行对比。通过MALDI-TOF质谱分析，我们证明这种方法能生成高质量、均一的聚合物，其端基分布狭窄。通过改变单体的电负性，我们初步实现了对这些端基的控制，按照电负性增加的顺序，分别形成双氢端基、单氢单溴端基或双溴端基的聚合物。

  DOI：

  10.1039/c0jm02359k

文献信息

• Development of naphtho[1,2-b:5,6-b′]dithiophene based novel small molecules for efficient bulk-heterojunction organic solar cells
  作者：Pranabesh Dutta、Wooseung Yang、Seung Hun Eom、Woo-Hyung Lee、In Nam Kang、Soo-Hyoung Lee

  DOI：10.1039/c1cc15465f

  日期：——

  Two new small molecules with a rigid planar naphtho[1,2-b:5,6-b']dithiophene (NDT) unit were designed and synthesized. Solution processed bulk-hetereojunction organic solar cells based on blends of the small molecules and [6,6]-phenyl-C(71)-butyric acid methyl ester (PC(71)BM) exhibited promising photovoltaic device performance with a maximum power conversion efficiency up to 2.20% under the illumination

  设计并合成了两个具有刚性平面萘[1,2-b：5,6-b']二噻吩（NDT）单元的新小分子。基于小分子和[6,6]-苯基-C（71）-丁酸甲酯（PC（71）BM）的混合物的固溶体异质结有机太阳能电池表现出了有希望的光伏器件性能和最大的功率转换在AM 1.5G，100 mW cm（-2）的光照下效率高达2.20％。
• Influence of molecular structure on the performance of low V_oc loss polymer solar cells
  作者：Ming Wang、Hengbin Wang、Michael Ford、Jianyu Yuan、Cheng-Kang Mai、Stephanie Fronk、Guillermo C. Bazan

  DOI：10.1039/c6ta07120a

  日期：——

  Two regioregular narrow bandgap conjugated polymers (PM1 and PM2) are prepared and their devices exhibit low V_oc loss and high short circuit current J_sc, but, most significantly, display improved fill factors compared to previously reported PIPCP.

  制备了两种区域规则的窄带隙共轭聚合物（PM1和PM2），它们的器件表现出低的Voc损失和高的短路电流Jsc，但最重要的是，与先前报道的PIPcP相比，填充因子得到了改善。
• Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers
  作者：Frank Brouwer、Jan Alma、Hennie Valkenier、Thomas P. Voortman、Jorrit Hillebrand、Ryan C. Chiechi、Jan C. Hummelen

  DOI：10.1039/c0jm02359k

  日期：——

  We demonstrate the use of bis(pinacolato)diboron to directly polymerize symmetric, bisbromo, thiophene-based monomers via a Suzuki homo-polymerization to form co-polymers in less steps than the corresponding co-polymerization. We compare this method to the commonly used Stille co-polymerization by preparing four thiophene-based co-polymers using both methods. We use MALDI-TOF mass spectrometry to show that this new method produces high-quality, uniform polymers with narrow distributions of end-groups. By varying the electronegativity of the monomers, we demonstrate rudimentary control over these end-groups, forming either bis-H-, mono-H-mono-Br-, or bis-Br-terminated polymers in order of increasing electronegativity.

  我们展示了通过Suzuki同聚合反应，利用双(频哪醇基)二硼直接聚合对称、双溴、噻吩基单体，以较少步骤形成共聚物的方法。通过采用两种方法（新方法和常用的Stille共聚法）制备四种噻吩基共聚物，并将这种方法与Stille共聚法进行对比。通过MALDI-TOF质谱分析，我们证明这种方法能生成高质量、均一的聚合物，其端基分布狭窄。通过改变单体的电负性，我们初步实现了对这些端基的控制，按照电负性增加的顺序，分别形成双氢端基、单氢单溴端基或双溴端基的聚合物。
• Dithiophene based X-shaped bolaamphiphiles: liquid crystals with single wall honeycombs and geometric frustration
  作者：Hongfei Gao、Yafei Ye、Leiyang Kong、Xiaohong Cheng、Marko Prehm、Helgard Ebert、Carsten Tschierske

  DOI：10.1039/c2sm26575c

  日期：——

  A series of 5,5′-diphenyl-2,2′-dithiophene based X-shaped polyphiles with two long lateral alkyl chains and terminal glycerol groups was synthesized and the liquid crystalline phases formed by these compounds were investigated by polarizing microscopy, DSC and XRD. These compounds form square (p4mm and p4gm) and hexagonal (p6mm) columnar LC phases. In these mesophases the molecules organize into polygonal honeycombs where the π-conjugated cores form the walls, fused at the edges by the hydrogen bonding networks between the glycerol units and filled by the lateral alkyl chains. By elongation of these chains, a series of polygonal honeycomb phases with a “single wall” structure, ranging from triangular via square and pentagonal to hexagonal was observed. Most triangular honeycombs appear to be defective and can be considered as mixtures of triangular cylinders with orientationally randomized rhombic cylinders. The transition from this improper triangular honeycomb to the square honeycomb takes place via a disordered isotropic phase. Addition of water to this isotropic phase gives rise to a true triangular honeycomb LC phase. Replacing one of the long lateral chains by a small methyl group leads to honeycombs formed by double walls instead of single walls. UV investigations indicate π-stacking of the aromatic cores organized in the honeycomb walls, which is of interest for the potential application of these materials in self assembled arrays of organic electronic material.

  合成了一系列基于5,5′-二苯基-2,2′-二硫代苯的X形聚合物，这些聚合物具有两个长侧链和端部甘油基团，并对这些化合物形成的液晶相进行了偏光显微镜、差示扫描量热法（DSC）和X射线衍射（XRD）研究。这些化合物形成了方形（p4mm和p4gm）和六角形（p6mm）柱状液晶相。在这些中间相中，分子组织成多边形蜂窝结构，π共轭核心形成墙壁，通过甘油单元之间的氢键网络在边缘连接，侧链则填充其中。通过延长这些链，观察到一系列具有“单墙”结构的多边形蜂窝相，形状从三角形到方形、五边形再到六角形。大多数三角形蜂窝似乎是缺陷结构，可以视为带有方向随机的菱形柱体的三角形柱体的混合体。这个不规则的三角形蜂窝到方形蜂窝的转变是通过一个无序的各向同性相进行的。向该各向同性相中添加水会产生一个真正的三角形蜂窝液晶相。用小的甲基取代其中一个长侧链会导致蜂窝形成双墙而不是单墙。紫外线研究表明，芳香核心在蜂窝墙中的堆叠现象，这对这些材料在自组装有机电子材料阵列中的潜在应用具有重要意义。
• Transition between triangular and square tiling patterns in liquid-crystalline honeycombs formed by tetrathiophene-based bolaamphiphiles
  作者：Xiaohong Cheng、Hongfei Gao、Xiaoping Tan、Xueyan Yang、Marko Prehm、Helgard Ebert、Carsten Tschierske

  DOI：10.1039/c3sc50664a

  日期：——

  self-assemble into a series of liquid-crystalline honeycombs, formed by the π-conjugated rods which enclose polygonal prismatic cells filled by the lateral chains. With increasing chain length a discontinuous transition from triangular to square honeycombs takes place. At this transition a periodic honeycomb composed of a mixture of square and triangular cells in a ratio 1 : 2 was formed at low temperature, whereas

  一系列5,5'''-二苯基四噻吩在两端各具有一个极性甘油基团和两个侧向柔性链，它们自组装成一系列液晶蜂窝，这些蜂窝由π共轭棒构成，这些棒包围了由多角形四方晶格填充的多角形晶格，侧链。随着链长的增加，发生了从三角形蜂窝到方形蜂窝的不连续过渡。在此过渡过程中，在低温下形成了由正方形和三角形单元以1：2的比例混合而成的周期性蜂窝，而在更高温度下，由三角形和随机分布的菱形单元组成的六方柱状相（一种新型的向列型向列型）由正方形蜂窝状碎片组成的均质相和等轴性各向同性相代表中间状态。