4-乙炔基苯甲醚 | 768-60-5

• 物质功能分类: 化学试剂 - 有机试剂 - 醚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-乙炔基苯甲醚
• 中文别名: 1-乙炔基-4-茴香醚；1-乙炔-4-甲氧基苯；4-甲氧基苯乙炔；(4-甲氧基苯基)乙炔
• 英文名称: 4-methoxyphenylacetylen
• 英文别名: p-methoxyethynylbenzene；1-ethynyl-4-methoxybenzene；4-ethynylanisole；4-methoxyphenylacetylene；p-methoxyphenylacetylene；para-methoxyphenylacetylene；1‐ethynyl‐4‐methoxybenzene；4-methoxylphenylacetylene；p-ethynylanisole
• CAS: 768-60-5
• 化学式: C₉H₈O
• 分子量: 132.162
• InChiKey: KBIAVTUACPKPFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  28-29 °C (lit.)
• 沸点：
  87-91 °C/11 mmHg (lit.)
• 密度：
  1.019 g/mL at 25 °C (lit.)
• 闪点：
  180 °F
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）
• 稳定性/保质期：
  常温常压下稳定，避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2909309090
• 危险品运输编号：
  UN 1325 4.1/PG 2
• 包装等级：
  II
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封储存于阴凉、干燥处。

SDS

Name:	1-Eth-1-ynyl-4-methoxybenzene 97% Material Safety Data Sheet
Synonym:	4-Methoxyphenylacetylen
CAS:	768-60-5

Section 1 - Chemical Product MSDS Name:1-Eth-1-ynyl-4-methoxybenzene 97% Material Safety Data Sheet
Synonym:4-Methoxyphenylacetylen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
768-60-5	1-Eth-1-ynyl-4-methoxybenzene	97%	unlisted

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

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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.

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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.
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. Combustible solid.
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:
Keep away from sources of ignition. 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# 768-60-5: 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: colorless to yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 87 - 91 deg C @11mmHg
Freezing/Melting Point: 28 - 30 deg C
Autoignition Temperature: Not available.
Flash Point: 82 deg C ( 179.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.019
Molecular Formula: C9H8O
Molecular Weight: 132

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 768-60-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Eth-1-ynyl-4-methoxybenzene - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 768-60-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 768-60-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 768-60-5 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

制备方法与用途

用途

4-乙炔基苯甲醚可作为有机砌块、医药中间体和通用试剂等使用。

反应信息

• 作为反应物：
  描述：

  4-乙炔基苯甲醚 在 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 、 1,2-二溴四氯乙烷 、 二苯基硅烷 、 2-tert-butylphenol potassium salt 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以74%的产率得到1-((E)-2-溴乙烯基)-4-甲氧基苯
  参考文献：
  名称：

  炔烃的催化反马尔科夫尼科夫氢溴化反应

  摘要：

  我们开发了第一种用于炔烃的反马尔科夫尼科夫氢溴化的催化方法。该反应以高产率和优异的区域选择性和非对映选择性提供末端 E-烯基溴化物。芳基和烷基取代的末端炔烃均可用作底物。此外，反应条件与多种官能团兼容，包括酯、腈、环氧化物、芳基硼酸酯、末端烯烃、甲硅烷基醚、芳基卤和烷基卤。对反应机理的初步研究表明，溴化氢反应包括炔烃的氢铜化，然后是烯基铜中间体的溴化。

  DOI：

  10.1021/ja503944n
• 作为产物：
  描述：

  2,3-二溴-3-(4-甲氧基-苯基)-丙酸 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 异丙醇 为溶剂， 反应 13.0h， 生成 4-乙炔基苯甲醚
  参考文献：
  名称：

  高双折射异硫氰酸苯乙炔基共混液晶的制备及性能

  摘要：

  摘要 合成并表征了一系列具有高双折射的烷氧基-苯乙炔-异硫氰酸酯结构的化合物。这些化合物的化学结构通过FT-IR和1 H-NMR确认，并测量转变温度和双折射。将这些具有良好液晶性能和高双折射的化合物与主液晶混合，形成混合液晶。讨论了化合物浓度对相温度范围、双折射、电阻率、介电各向异性和光电性能的影响。结果表明，共混液晶（含7 wt%的化合物）表现出优异的综合性能。

  DOI：

  10.1080/15421406.2022.2055259
• 作为试剂：
  描述：

  乙酸肉桂酯 在 copper (I) acetate 、 4-乙炔基苯甲醚 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙腈 为溶剂， 以66 %的产率得到(Z)-乙酸肉桂酯
  参考文献：
  名称：

  Cu-乙酰化物配合物通过能量转移实现烯烃的光异构化

  摘要：

  人们发现乙炔铜配合物可作为可见光敏剂，将能量转移至烯烃。在此基础上，在蓝光照射下进行了具有不同官能团的烯烃的E→Z光异构化反应，具有中等到高选择性。机理研究表明，该反应涉及从光激发乙炔铜通过单重激发态到烯烃的能量转移（EnT）。

  DOI：

  10.1002/ejoc.202300948

文献信息

• Highly regio- and stereoselective hydrothiolation of acetylenes with thiols catalyzed by a well-defined supported Rh complex
  作者：Yong Yang、Robert M. Rioux

  DOI：10.1039/c1cc11605c

  日期：——

  Highly regio- and stereoselective hydrothiolation of a wide range of alkynes with various thiols was demonstrated in the presence of a well-defined Rh complex supported on mesoporous SBA-15 silica. The catalyst was easily recovered and reused several times without significant loss of activity or selectivity.

  在存在于介孔SBA-15二氧化硅上的明确定义的Rh配合物的存在下，证明了各种炔与各种硫醇的高度区域选择性和立体选择性氢硫醇化作用。催化剂容易回收并重复使用几次，而活性或选择性没有明显损失。
• Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs
  作者：Christopher J. Smedley、Gencheng Li、Andrew S. Barrow、Timothy L. Gialelis、Marie‐Claire Giel、Alessandra Ottonello、Yunfei Cheng、Seiya Kitamura、Dennis W. Wolan、K. Barry Sharpless、John E. Moses

  DOI：10.1002/anie.202003219

  日期：2020.7.20

  Diversity Oriented Clicking (DOC) is a unified click‐approach for the modular synthesis of lead‐like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease” , by combining classic C−C π‐bond click chemistry with recent developments in connective SuFEx‐technologies. We showcase 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluorides

  面向多样性的点击 (DOC) 是一种统一的点击方法，用于通过应用广泛的点击转换家族来模块化合成类先导结构。DOC 从实现“轻松实现多样性”的概念演变而来，将经典的 C−C π 键点击化学与连接性 SuFEx 技术的最新发展相结合。我们展示了 2-取代的- A炔基-1-磺酰基F氟化物（SASFs）作为一类新的连接枢纽，与多种点击环加成过程相结合。通过具有一系列偶极子和环状二烯的 SASF 的选择性 DOC，我们以最少的合成步骤报告了 173 种独特功能分子的多样化点击库。SuFExable 库包含 10 个离散的杂环核心结构，这些核心结构源自 1,3- 和 1,5- 偶极子；而与环状二烯的反应会产生几种三维双环 Diels-Alder 加合物。通过对 96 孔板中的磺酰氟侧基进行 SuFEx 点击衍生化，可以通过后期修饰将文库增加到 278 种离散化合物——证明了 DOC 方法在快速合成不同功能结构方面的多功能性。
• Synthesis, biological activities and structure−activity relationships for new avermectin analogues
  作者：Jian Zhang、Xiang Nan、Hai-Tao Yu、Pi-Le Cheng、Yan Zhang、Ying-Qian Liu、Shao-Yong Zhang、Guan-Fang Hu、Huanxiang Liu、An-Liang Chen

  DOI：10.1016/j.ejmech.2016.05.056

  日期：2016.10

  LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 μM, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides.

  为了发现具有良好杀虫活性的新分子，合成了40多种新的阿维菌素衍生物，并评估了它们对三种物种的蜘蛛，昆虫和线虫的生物活性，这些物种分别是朱砂叶螨（Tetranychus Cinnabarinus），蚜虫（Aphis craccivora）和松柏xylophilus。所有测试的化合物均显示出对三种昆虫的有效抑制活性。值得注意的是，大多数化合物对朱砂毛虫表现出高选择性，其中一些与阿维菌素相比具有更好的选择性。特别是化合物9j（LC 50：0.005μM）和16d（LC 50：0.002μM）对朱砂丁香的活性分别比阿维菌素（LC 50： 0.013μM ）高2.5倍和4.7倍。此外，化合物9B，9D-F ，9H，9J，9升，9N，9P，9R，9V和17D显示了优良的活性与LC 50个相比的2.959-5.013μM的值1（LC 50： 6.746μM）对乙。松材线虫。同时，化合物9f，9g，9h和9m的杀虫活性针对A
• Ancillary ligand-free copper catalysed hydrohydrazination of terminal alkynes with NH₂NH₂
  作者：Jesse L. Peltier、Rodolphe Jazzar、Mohand Melaimi、Guy Bertrand

  DOI：10.1039/c5cc10427k

  日期：——

  An efficient and selective Cu-catalysed hydrohydrazination of terminal alkynes with parent hydrazine is reported. The methodology tolerates a broad range of functional groups, allows for the synthesis of symmetrical and...

  报道了末端炔与母体肼的有效且选择性的Cu催化的水合肼化作用。该方法可以耐受各种官能团，可以合成对称和...
• Synthesis of 3-Pyrrolin-2-ones by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with Ketene Silyl Acetal
  作者：Rui-Qiao Ran、Jun He、Shi-Dong Xiu、Kai-Bing Wang、Chuan-Ying Li

  DOI：10.1021/ol501514b

  日期：2014.7.18

  α-Imino rhodium carbenoids generated from 1-sulfonyl 1,2,3-triazole were applied to the 3 + 2 cycloaddition with ketene silyl acetal, offering a novel and straightforward synthesis of biologically interesting compound 3-pyrrolin-2-one with broad substrate scope.

  由1-磺酰基1,2,3-三唑生成的α-氨基铑类胡萝卜素与乙烯酮甲硅烷基缩醛应用于3 + 2环加成反应，提供了一种新颖而直接的合成方法，可合成具有广泛底物的生物学上令人感兴趣的化合物3-吡咯啉-2-酮范围。

表征谱图