5-(2-苯乙基-1-基)噻吩-2-甲苯 | 17257-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-(2-苯乙基-1-基)噻吩-2-甲苯
• 中文别名: 5-(2-苯乙基-1-基)噻吩-2-甲醛
• 英文名称: 5-(phenylethynyl)thiophene-2-carboxaldehyde
• 英文别名: 5-(2-phenyleth-1-ynyl)thiophene-2-carbaldehyde；5-(2-phenylethynyl)thiophene-2-carbaldehyde；5-(phenylethynyl)thiophene-2-carbaldehyde；2-formyl-5-(phenylethynyl)-thiophene；2-formyl-5-(phenylethynyl)thiophene；5-Phenylethynyl-thiophene-2-carbaldehyde
• CAS: 17257-10-2
• 化学式: C₁₃H₈OS
• mdl: MFCD00126374
• 分子量: 212.272
• InChiKey: YFMUACLZRVJOBK-UHFFFAOYSA-N

物化性质

• 沸点：
  388.6±27.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R22
• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302,H413

SDS

Name:	5-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde 97% Material Safety Data Sheet
Synonym:	5-(Phenylethynyl)thiophene-2-carboxaldehyd
CAS:	17257-10-2

Section 1 - Chemical Product MSDS Name:5-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde 97% Material Safety Data Sheet
Synonym:5-(Phenylethynyl)thiophene-2-carboxaldehyd

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17257-10-2	5-(2-Phenyleth-1-ynyl)thiophene-2-carb	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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.
Notes to Physician:
Treat symptomatically and supportively.

---

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.

---

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.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 17257-10-2: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 93 - 95 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: C13H8OS
Molecular Weight: 212

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17257-10-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 17257-10-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17257-10-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17257-10-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(2-苯乙基-1-基)噻吩-2-甲苯 在 sodium tetrahydroborate 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 2-(chloromethyl)-5-(phenylethynyl)thiophene
  参考文献：
  名称：

  五元杂芳烃与烯丙基三丁基锡烷的钯催化区域选择性烯丙基化。

  摘要：

  在这项研究中描述了钯催化的2-（氯甲基）噻吩，2-（氯甲基）呋喃和N-保护的2-（氯甲基）-1H-吡咯与烯丙基三丁基锡烷的烯丙基化反应。这种类型的烯丙基化反应区域选择性地发生在杂芳烃环上，以令人满意的产率产生烯丙基化的脱芳香化产物或烯丙基化的杂芳烃。

  DOI：

  10.1039/c4cc10373d
• 作为产物：
  描述：

  1-methyl-4-((phenylethynyl)sulfonyl)benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.42h， 生成 5-(2-苯乙基-1-基)噻吩-2-甲苯
  参考文献：
  名称：

  A straightforward alkynylation of Li and Mg metalated heterocycles with sulfonylacetylenes

  摘要：

  将炔基团与杂环环上偶联，而无需使用过渡金属，可以通过芳基或杂环磺酰乙炔与杂环锂化合物或其对应的反应性较低的镁衍生物反应来轻松实现。

  DOI：

  10.1039/c4cc07574a

文献信息

• Reaction between Azidyl Radicals and Alkynes: A Straightforward Approach to<i>NH</i>-1,2,3-Triazoles
  作者：Long Hu、Christian Mück-Lichtenfeld、Tao Wang、Guifeng He、Meng Gao、Junfeng Zhao

  DOI：10.1002/chem.201504515

  日期：2016.1.18

  Reaction between nitrogen‐centered radicals and unsaturated C−C bonds is an effective synthetic strategy for the construction of nitrogen‐containing molecules. Although the reactions between nitrogen‐centered radicals and alkenes have been studied extensively, their counterpart reactions with alkynes are extremely rare. Herein, the first example of reactions between azidyl radicals and alkynes is described

  以氮为中心的自由基与不饱和C-C键之间的反应是构建含氮分子的有效合成策略。尽管已经广泛研究了以氮为中心的自由基与烯烃之间的反应，但它们与炔烃的对应反应却极为罕见。在此，描述叠氮基和炔之间的反应的第一个例子。该反应引发了一个有效的级联反应，涉及向C-C三键的分子间/分子内自由基均溶加成和氢原子转移步骤，从而提供了一种直接的NH方法-1,2,3-三唑在温和的反应条件下。内部炔烃和末端炔烃都很好地用于该转化，并且炔烃上的一些杂环取代基是相容的。这种机制上截然不同的策略克服了与叠氮化物阴离子化学反应相关的固有局限性，并且代表了氮中心自由基与炔烃之间反应的罕见例子。
• Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings
  作者：Akihiro Orita、Fangguo Ye、Govindarajulu Babu、Tomohiro Ikemoto、Junzo Otera

  DOI：10.1139/v05-038

  日期：2005.6.1

  The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.Key words: arylene–ethynylenes, heteroaromatic rings, ferrocene, double elimination, sulfones.

  β-取代磺酮的双消除反应提供了一种多功能的合成芳基乙炔基套件的策略，其中包含杂芳环。 α-磺酰基碳负离子与醛之间的醛缩反应序列，捕获所得的醛缩物以给出β-取代磺酮，以及对该中间体的双消除可以集成在一个反应器中。该方案允许噻吩、吡啶和二茂铁单元被容纳在苯基乙炔基阵列中。关键词：芳基-乙炔基，杂芳环，二茂铁，双消除，磺酮。
• Library Screening by Means of Mass Spectrometry (MS) Binding Assays-Exemplarily Demonstrated for a Pseudostatic Library Addressing γ-Aminobutyric Acid (GABA) Transporter 1 (GAT1)
  作者：Miriam Sindelar、Klaus T. Wanner

  DOI：10.1002/cmdc.201200201

  日期：2012.9

  assays as a tool for library screening is reported. For library generation, dynamic combinatorial chemistry (DCC) was used. These libraries can be screened by means of MS binding assays when appropriate measures are taken to render the libraries pseudostatic. That way, the efficiency of MS binding assays to determine ligand binding in compound screening with the ease of library generation by DCC is combined

  在本研究中，报道了质谱（MS）结合测定作为文库筛选工具的应用。对于文库生成，使用了动态组合化学（DCC）。当采取适当的措施使文库具有伪静态性时，可以通过MS结合测定法筛选这些文库。通过这种方式，结合了MS结合测定在化合物筛选中确定配体结合的效率以及DCC产生文库的简便性。以γ-氨基丁酸（GABA）转运蛋白1（GAT1）为靶标，表明了该方法的可行性，代表了GABA转运蛋白的最重要亚型。为了筛选 employed文库的使用是在靶标存在下通过使各种醛类与肼衍生物反应而生成的，肼衍生物是哌啶-3-羧酸（庚酸）（已知的GAT1抑制剂的常见片段）所描绘的。为了确保生成的文库是假静态的，请使用大量过量的菜酸衍生物。由于文库是在适合结合的缓冲液系统中生成的，并且已经存在靶标，因此可以通过MS结合测定法直接分析混合物-库生成和筛选的过程因此变得易于执行。通过反卷积鉴定的命中的结合亲和力在用通过单独合成获得的
• Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries
  作者：Tobias J. Hauke、Thomas Wein、Georg Höfner、Klaus T. Wanner

  DOI：10.1021/acs.jmedchem.8b01602

  日期：2018.11.21

  study describes the screening of dynamic combinatorial libraries based on nipecotic acid as core structure with substituents attached to the 5- instead of the common 1-position for the search of novel inhibitors of the GABA transporter GAT1. The generated pseudostatic hydrazone libraries included a total of nearly 900 compounds and were screened for their binding affinities toward GAT1 in competitive mass

  这项研究描述了筛选以菊苣酸为核心结构的动态组合文库的筛选方法，该结构具有取代基附着在5位而不是常见的1位上，以寻找GABA转运蛋白GAT1的新型抑制剂。生成的伪静态文库总共包含近900种化合物，并在基于竞争质谱（MS）的结合试验中筛选了它们对GAT1的结合亲和力。最高亲和力的腙表征（与顺-构型外消旋- 16gf结合和吸收实验中带有一个5-（1-萘基）呋喃-2-基残基和一个最有效的四原子间隔基）揭示了GAT1的变构相互作用，迄今为止尚无关于其他任何尼克酸衍生物的报道。因此，本文引入的5-取代的庚酸衍生物可以用作研究由GAT1介导的变构调节的GABA转运的有价值的工具，并且还可以作为新一类GAT1抑制剂的起点。
• Tetrahydroquinoline derivatives as antithrombotic agents
  申请人：——

  公开号：US20030225110A1

  公开（公告）日：2003-12-04

  This invention relates generally to tetracyclic tetrahydroquinoline compounds, and analogues thereof, and pharmaceutically acceptable salt forms thereof, which are selective inhibitors of serine protease enzymes, especially factor VIIa; pharmaceutical compositions containing the same; and methods of using the same as anticoagulant agents for modulation of the coagulation cascade.

  这项发明通常涉及四环四氢喹啉化合物及其类似物，以及其药用盐形式，这些化合物是选择性抑制丝氨酸蛋白酶酶，特别是VIIa因子的；含有同样化合物的药物组合物；以及将其用作抗凝剂调节凝血级联的方法。