5-(噻吩-2-基)噻吩-2-甲腈 | 16278-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 5-(噻吩-2-基)噻吩-2-甲腈
• 英文名称: 2,2'-bithiophene-5-carbonitrile
• 英文别名: 5-cyano-2,2'-bithiophene；5-(Thien-2-yl)thiophene-2-carbonitrile；5-thiophen-2-ylthiophene-2-carbonitrile
• CAS: 16278-99-2
• 化学式: C₉H₅NS₂
• mdl: MFCD01812635
• 分子量: 191.277
• InChiKey: ANARYBGZNUMARH-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  36 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2934999090

SDS

Name:	5-(Thien-2-yl)thiophene-2-carbonitrile 97% Material Safety Data Sheet
Synonym:
CAS:	16278-99-2

Section 1 - Chemical Product MSDS Name:5-(Thien-2-yl)thiophene-2-carbonitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16278-99-2	5-(Thien-2-yl)thiophene-2-carbonitrile	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16278-99-2: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 73 - 75 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H5NS2
Molecular Weight: 191.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16278-99-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(Thien-2-yl)thiophene-2-carbonitrile - 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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 16278-99-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16278-99-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16278-99-2 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：

  5-(噻吩-2-基)噻吩-2-甲腈 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到5'-溴-[2,2'-联噻吩]-5-甲腈
  参考文献：
  名称：

  Ismail, Mohamed A., Journal of Chemical Research, 2006, # 11, p. 733 - 737

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-联二噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(噻吩-2-基)噻吩-2-甲腈
  参考文献：
  名称：

  取代基对共轭二芳基四嗪的氧化还原，光谱和结构性质的影响-结合实验和理论研究†

  摘要：

  两套新的可溶性共轭化合物 四嗪中心环已合成。三环化合物是通过芳基反应合成的氰化物 （其中芳基= 噻吩基，烷基噻吩基，苯基或吡啶基）与 肼 然后用 偶氮二羧酸二乙酯。五环化合物已通过两种途径制备：（i）5-氰基-2,2'-联噻吩 （或其烷基衍生物）与 肼; （ii）通过Suzuki或Stille联轴器3,6-双（5-溴-2-噻吩基）-1,2,4,5-四嗪 与斯坦尼或 硼酸盐烷基噻吩的衍生物。紫外-可见的合成的化合物的光谱性质强烈地依赖于该芳基，增溶取代基的位置和该分子的长度，显示出最高红移的性质（λ最大> 440纳米）为5环化合物用烷基连接到C α 碳 在终端 噻吩基戒指。已经找到了极好的线性相关性，可用于光谱测定和理论计算（TD-B3LYP/ 6-31G *）激发能量。除了双吡啶导数，根据电化学数据，所研究分子的最低未占据分子轨道（LUMO）水平在狭窄范围内变化（从-2.63至-2.41

  DOI：

  10.1039/c0cp01553a

文献信息

• Solvent assisted fluorescence modulation of a C₃-symmetric organogelator
  作者：Deepak D. Prabhu、Aneesh P. Sivadas、Suresh Das

  DOI：10.1039/c4tc01008f

  日期：——

  The synthesis and self-assembling properties of C3 symmetric donor–acceptor molecules containing 1,3,4-oxadiazole and bisthiophene moieties in the core functionalized with octyl (BTOX8) and dodecyl (BTOX12) substituted phenyl acetylene units at the periphery are reported. BTOX8 was found to form gels only in aliphatic solvents, whereas BTOX12 formed gels in both aliphatic and aromatic solvents. Photophysical analysis of BTOX12 solutions showed a striking effect of the solvent on the nature of the self-assembled aggregate formed. Our studies indicate that in aliphatic solvents such as n-decane the solvent molecules interact mainly with the alkyl regions of BTOX12. As a result the π–π interaction between the neighbouring molecules becomes feasible resulting in strong excitonic coupling between the neighbouring molecules leading to excimer type emission. In aromatic solvents the solvent molecules interact mainly with the chromophoric part of BTOX12 resulting in reduced π-stacking between the molecules in the aggregate leading to monomer type emission. Films prepared from aliphatic and aromatic solvents exhibited photophysical properties significantly similar to those observed in the respective solvents. Photophysical studies of the films indicated that the films prepared from n-decane exhibited an H-type molecular arrangement whereas the films prepared from toluene exhibited a slipped stack J-type arrangement.

  报道了含有1,3,4-恶二唑和双噻吩部分的C3对称施受体分子的合成及自组装特性，这些分子的核心功能化为具有八烷基（BTOX8）和十二烷基（BTOX12）取代的苯乙炔单元。在脂肪溶剂中，发现BTOX8仅形成凝胶，而BTOX12在脂肪和芳烃溶剂中均形成凝胶。对BTOX12溶液的光物理分析表明，溶剂对形成的自组装聚集体的性质有显著影响。我们的研究表明，在如正癸烷等脂肪溶剂中，溶剂分子主要与BTOX12的烷基区域相互作用。因此，临近分子之间的π-π相互作用变得可行，从而导致临近分子之间强的激子耦合，进而引发类激发二聚体的发射。而在芳烃溶剂中，溶剂分子主要与BTOX12的发色团部分相互作用，导致聚集体中分子之间的π堆叠减少，进而产生单体型发射。从脂肪和芳烃溶剂中制备的薄膜表现出与各自溶剂中观察到的光物理特性显著相似。薄膜的光物理研究表明，用正癸烷制备的薄膜表现出H型分子排列，而用甲苯制备的薄膜表现出错位堆叠的J型排列。
• Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells
  作者：Peng An、Zhipeng Yu、Qing Lin

  DOI：10.1039/c3cc45752d

  日期：——

  A 405 nm light-activatable terthiophene-based tetrazole was designed that reacts with a fumarate dipolarophile with the second-order rate constant k2 exceeding 10(3) M(-1) s(-1). The utility of this laser-activatable tetrazole in imaging microtubules in a spatiotemporally controlled manner in live cells was demonstrated.

  405 nm 光活化三噻吩基四唑被设计为与富马酸盐偶极体反应，二阶速率常数 k2 超过 10(3) M(-1) s(-1)。证明了这种激光可激活四唑在活细胞中以时空控制方式成像微管中的效用。
• Influence of substitution pattern and enhanced π-conjugation on a family of thiophene functionalized 1,5-dithia-2,4,6,8-tetrazocines
  作者：François Magnan、Ilia Korobkov、Jaclyn Brusso

  DOI：10.1039/c5nj01345c

  日期：——

  The versatile, one-pot synthesis of a series of π-extended 1,5,2,4,6,8-dithiatetrazocines is described, along with their optoelectronic and structural properties.

  描述了一种多功能、一锅法合成一系列π扩展的1,5,2,4,6,8-二硫代四唑烷化合物的方法，以及它们的光电和结构性质。
• Compromise between conjugation length and charge-transfer in nonlinear optical η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands: Synthesis, electrochemical studies and first hyperpolarizabilities
  作者：M. Helena Garcia、Paulo J. Mendes、M. Paula Robalo、A. Romão Dias、Jochen Campo、Wim Wenseleers、Etienne Goovaerts

  DOI：10.1016/j.jorganchem.2007.03.023

  日期：2007.6

  series of η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands of general formula [FeCp(P_P)(NCSC4H2}nNO2)][PF6] (P_P = dppe, (+)-diop; n = 1–3) has been synthesized and characterized. The electrochemical behaviour of the new compounds was explored by cyclic voltammetry. Quadratic hyperpolarizabilities (β) of the complexes with dppe coligands have been determined

  一个系统的一系列的η 5通式-monocyclopentadienyliron（II）配合物与取代的低聚噻吩腈配体[FeCp（P_P）（NC SC 4 ħ 2 } Ñ NO 2）] [PF 6 ]（P_P = DPPE，（ +）-diop；n  = 1-3）已合成并表征。通过循环伏安法研究了新化合物的电化学行为。已经通过在1.064和1.550μm的两个基本波长下的超瑞利散射（HRS）测量来确定具有DPPE大分子配体的二次超极化率（β），以揭示双光子共振效应并估计静态β价值观。将所得到的总的结果被发现是比用于相关η更好5 -monocyclopentadienyliron（II）络合物与p -苄腈衍生物。虽然增加了谐振的β在1.064微米与在共轭配体增加的噻吩单元的数目被发现（高达910×10 -30  ESU），静态值β 0保持几乎不变，如图中的1.550微米测量。结合电化学和光谱数据
• Stable and reusable Ni-based nanoparticles for general and selective hydrogenation of nitriles to amines
  作者：Zhuang Ma、Vishwas G. Chandrashekhar、Bei Zhou、Asma M. Alenad、Nils Rockstroh、Stephan Bartling、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1039/d2sc02961h

  日期：——

  The applicability of the optimal catalyst material is shown by hydrogenation of >110 diverse aliphatic and aromatic nitriles including functionalized and industrially relevant substrates. Challenging heterocyclic nitriles, specifically cyanopyridines, provided the corresponding primary amines in good to excellent yields. The resulting amines serve as important precursors and intermediates for the preparation

  二氧化硅负载的超小 Ni 纳米颗粒允许在温和条件下将各种腈类普遍和选择性地氢化为伯胺。通过煅烧由 Ni( II ) 生成的模板材料)硝酸盐和胶体二氧化硅在空气下，随后在分子氢存在下还原，制备最佳催化剂。制备的负载型纳米颗粒稳定，使用方便，易于回收利用。最佳催化剂材料的适用性通过对超过 110 种不同的脂肪族和芳香族腈（包括功能化和工业相关底物）进行氢化来证明。具有挑战性的杂环腈，特别是氰基吡啶，以良好的收率提供了相应的伯胺。所得胺可作为制备众多生命科学产品和聚合物的重要前体和中间体。