3-(2,2,2-三氟乙氧基)丙腈 | 272128-06-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-(2,2,2-三氟乙氧基)丙腈
• 英文名称: 3-(2,2,2-trifluoroethoxy)propanenitrile
• 英文别名: 3-(2,2,2-trifluoroethoxy)propionitrile
• CAS: 272128-06-0
• 化学式: C₅H₆F₃NO
• mdl: MFCD07784292
• 分子量: 153.104
• InChiKey: QGICCSXJVXICAY-UHFFFAOYSA-N

物化性质

• 沸点：
  186
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  T
• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(2,2,2-Trifluoroethoxy)propanenitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-(2,2,2-Trifluoroethoxy)propanenitrile
CAS number: 272128-06-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H6F3NO
Molecular weight: 153.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(2,2,2-三氟乙氧基)丙腈 以 乙腈 为溶剂， 反应 56.0h， 生成 1-(3,5-bis(trifluoromethyl)phenyl)-3-(3-(2,2,2-trifluoroethoxy)propyl)thiourea
  参考文献：
  名称：

  腈的水分辅助硼氢化反应及其转化为 N-杂环和含氮衍生物

  摘要：

  隐藏硼烷催化的最新发现彻底改变了有机合成中催化硼氢化领域。许多亲核反应促进剂，以前被认为是催化剂，实际上主要促进硼烷（BH 3 ）的形成，随后硼烷充当真正的催化剂。这一发现促使我们探索这些意想不到的转变的未开发潜力，以期使用更具成本效益和环境友好的亲核预催化剂来简化硼氢化反应。通过计算研究，我们能够确定水实际上可以发挥这一作用。在此，我们报告了一项关于腈的简单硼氢化反应的研究，腈是一种众所周知的具有挑战性但具有合成价值的底物，仅使用水分作为活化剂。这种水分辅助的腈硼氢化工艺可以以一锅方式与一系列下游转化无缝集成，生产有价值的含氮产品，例如对称亚胺、硫脲和双（醇）胺以及N-杂环，例如吡咯、吡啶、吡啶鎓盐、2-亚氨基噻唑啉和咔唑。

  DOI：

  10.1021/acs.orglett.3c03533
• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 丙烯腈 在 [μN,κP,κC,κN-{2-(i-Pr2PO),6-(CH2NBn)-(C6H3)}Ni]2 作用下， 以 苯 为溶剂， 反应 5.5h， 以100%的产率得到3-(2,2,2-三氟乙氧基)丙腈
  参考文献：
  名称：

  衍生自具有二级胺供体基团的Pincer配体的单体和二聚体镍配合物

  摘要：

  NiBr 2（CH 3 CN）x与不对称钳位配体m-（i -Pr 2 PO）（CH 2 NHBn）C 6 H 4（Bn = CH 2 Ph）的反应生成配合物（R，S）-κ P，κ ç，κ ñ - {2-（我-Pr 2 PO），6-（CH 2 NHBn）-C 6 H ^ 3 }的Ni II BR，1，具有不对称的仲胺供体部分。后者与甲基锂去质子化，得到暗棕色化合物不能被直接表征，但此化合物制备充分表征衍生物表明它是14电子酰氨物种[κ的溴化锂加合物P，κ Ç，κ Ñ -{2-（i -Pr 2 PO），6-（CH 2 NBn）-C 6 H 3 } Ni]，2。因此，2·LiBr与水反应生成1，而与过量的苄基或烯丙基溴反应生成POCN型钳形配合物3和4。分别具有叔胺供体部分。在另一方面，加热2·溴化锂在60℃下导致的LiBr的损失和二聚化以产生橙色结晶化合物[μ Ñ ;κ P，κ Ç，κ ñ -

  DOI：

  10.1021/ic100914x

文献信息

• Hydroamination and Alcoholysis of Acrylonitrile Promoted by the Pincer Complex {κ^<i>P</i>,κ^<i>C</i>,κ^<i>P</i>-2,6-(Ph₂PO)₂C₆H₃}Ni(OSO₂CF₃)
  作者：Abderrahmen B. Salah、Caroline Offenstein、Davit Zargarian

  DOI：10.1021/om200549p

  日期：2011.10.24

  describes the catalytic activity of the pincer-type complex κP,κC,κP-2,6-(Ph2PO)2C6H3}Ni(OSO2CF3) (1) in the anti-Markovnikov addition of aliphatic and aromatic amines and alcohols to acrylonitrile, crotonitrile, and methacrylonitrile. The influence of additives on the catalytic activities was investigated, and it was found that substoichiometric quantities of water promoted the C–N bond forming reactions

  本报告描述了钳型κ络合物的催化活性P，κ Ç，κ P -2,6-（PH 2 PO）2 C ^ 6 ħ 3 }的Ni（OSO 2 CF 3）（1）在反-Markovnikov将脂肪族和芳香族胺和醇添加到丙烯腈，巴豆腈和甲基丙烯腈中。研究了添加剂对催化活性的影响，发现亚化学计量的水促进了1催化的C–N键形成反应，特别是涉及芳族胺的反应。相比之下，NEt 3产生的影响较小。对于由1促进的丙烯腈的醇解，观察到相反的模式：水对这些反应没有任何有益作用，而NEt 3被证明是有效的促进剂。这些反应之间的另一个重要区别是，氢化胺化反应与更多的亲核胺能更好地发挥作用，而醇解反应与ArOH，CF 3 CH 2 OH和ArCH 2 OH则能很好地发挥作用，但与更多的亲核脂肪族醇，甲醇，乙醇和2-丙醇。相比于其Me取代的丁烯腈和甲基丙烯腈衍生物，丙烯腈的加氢胺化和醇解反应都进行得更好。在优化条件下，预催化剂1促
• Monomeric and Dimeric Nickel Complexes Derived from a Pincer Ligand Featuring a Secondary Amine Donor Moiety
  作者：Denis M. Spasyuk、Davit Zargarian

  DOI：10.1021/ic100914x

  日期：2010.7.5

  a C2-symmetric dimer involving four Ni−N interactions and a Ni2N2 core featuring a short Ni−Ni distance (2.51 Å). Preliminary reactivity tests have shown that 5 is stable toward weak nucleophiles such as acetonitrile but reacts with strong nucleophiles such as CO or 2,6-Me2(C6H3)NC. Reactions with protic reagents showed that phthalimide appears to break the dimer to generate a monomeric species, whereas

  NiBr 2（CH 3 CN）x与不对称钳位配体m-（i -Pr 2 PO）（CH 2 NHBn）C 6 H 4（Bn = CH 2 Ph）的反应生成配合物（R，S）-κ P，κ ç，κ ñ - 2-（我-Pr 2 PO），6-（CH 2 NHBn）-C 6 H ^ 3 }的Ni II BR，1，具有不对称的仲胺供体部分。后者与甲基锂去质子化，得到暗棕色化合物不能被直接表征，但此化合物制备充分表征衍生物表明它是14电子酰氨物种[κ的溴化锂加合物P，κ Ç，κ Ñ -2-（i -Pr 2 PO），6-（CH 2 NBn）-C 6 H 3 } Ni]，2。因此，2·LiBr与水反应生成1，而与过量的苄基或烯丙基溴反应生成POCN型钳形配合物3和4。分别具有叔胺供体部分。在另一方面，加热2·溴化锂在60℃下导致的LiBr的损失和二聚化以产生橙色结晶化合物[μ Ñ ;κ P，κ Ç，κ ñ -
• Platinum analogs with bis-nitrile-containing ligands
  申请人：Chen Xinghai

  公开号：US20080194680A1

  公开（公告）日：2008-08-14

  Disclosed herein are novel platinum-based analogs possessing two nitrile substituent groups (bis-nitrile) covalently-bonded to the platinum. Also disclosed herein are the reaction schemes for the synthesis of said platinum complexes, as well as quantitative in vitro IC50 data.

  本文披露了一种新型的铂基类似物，具有两个腈基取代基团（双腈基）共价连接到铂上。本文还披露了用于合成这些铂配合物的反应方案，以及定量体外IC50数据。
• Understanding cyclic(alkyl)(amino)carbene–copper complex catalysed N–H and O–H bond addition to electron deficient olefins
  作者：Akshi Tyagi、Sunita Mondal、Anmol、Vikas Tiwari、Tarak Karmakar、Subrata Kundu

  DOI：10.1039/d2cc05613e

  日期：——

  The hydroamination of electron-deficient olefins was carried out using the (CAAC)Cu–Cl (CAAC = cyclic (alkyl)(amino)carbene) catalyst with an excellent yield at room temperature and under an open atmosphere. Furthermore, the catalyst shows excellent efficiency in the hydroaryloxylation and hydroalkoxylation of alkenes under mild conditions. The efficiency of the catalyst was tested for a wide range

  使用 (CAAC)Cu-Cl（CAAC = 环状（烷基）（氨基）卡宾）催化剂对缺电子烯烃进行加氢胺化，在室温和开放气氛下具有优异的收率。此外，该催化剂在温和条件下对烯烃进行加氢芳氧基化和加氢烷氧基化反应时表现出优异的效率。针对具有不同电子和空间功能的各种底物测试了催化剂的效率。已经进行了详细的计算研究以了解这些 Cu( I ) 催化反应的机理，结果表明反应通过包含铜离子的四元或六元循环过渡态进行。
• Moisture-Assisted Hydroboration of Nitriles and Conversion Thereof to <i>N</i>-Heterocyles and <i>N</i>-Containing Derivatives
  作者：Son Hoai Doan、Binh Khanh Mai、Thanh Vinh Nguyen

  DOI：10.1021/acs.orglett.3c03533

  日期：2023.12.22

  synthesis. Many nucleophilic reaction promoters, previously believed to be the catalysts, in fact primarily facilitated the formation of borane (BH3), which subsequently acted as the true catalyst. This revelation prompted us to explore the untapped potential of these unexpected transformations, with a view to simplify hydroboration using more cost-effective and environmentally friendly nucleophilic precatalysts

  隐藏硼烷催化的最新发现彻底改变了有机合成中催化硼氢化领域。许多亲核反应促进剂，以前被认为是催化剂，实际上主要促进硼烷（BH 3 ）的形成，随后硼烷充当真正的催化剂。这一发现促使我们探索这些意想不到的转变的未开发潜力，以期使用更具成本效益和环境友好的亲核预催化剂来简化硼氢化反应。通过计算研究，我们能够确定水实际上可以发挥这一作用。在此，我们报告了一项关于腈的简单硼氢化反应的研究，腈是一种众所周知的具有挑战性但具有合成价值的底物，仅使用水分作为活化剂。这种水分辅助的腈硼氢化工艺可以以一锅方式与一系列下游转化无缝集成，生产有价值的含氮产品，例如对称亚胺、硫脲和双（醇）胺以及N-杂环，例如吡咯、吡啶、吡啶鎓盐、2-亚氨基噻唑啉和咔唑。