2-三氟乙酰基吡啶 | 33284-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-三氟乙酰基吡啶
• 中文别名: 2,2,2-三氟-1-(2-吡啶)乙酮
• 英文名称: 2,2,2-trifluoro-1-(pyridin-2-yl)ethanone
• 英文别名: 2-(trifluoroacetyl)pyridine；2,2,2-trifluoro-1-pyridin-2-ylethanone
• CAS: 33284-17-2
• 化学式: C₇H₄F₃NO
• mdl: MFCD07380748
• 分子量: 175.11
• InChiKey: WBDGOEPVBPCRLY-UHFFFAOYSA-N

物化性质

• 沸点：
  172.9±35.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温且干燥环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Trifluoroacetyl)pyridine
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: 2-(Trifluoroacetyl)pyridine
CAS number: 33284-17-2

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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, refrigerated.
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: C7H4F3NO
Molecular weight: 175.1

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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：

  2-三氟乙酰基吡啶 在 正丁基锂 、 对甲苯磺酰肼 、 sodium hydroxide 作用下， 以 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 8.33h， 生成 2,2,2-trifluoro-1-[3-(trifluoromethyl)-[1,2,3]triazolo[1,5-a]pyridin-7-yl]ethane-1,1-diol
  参考文献：
  名称：

  Approaches for the introduction of fluorinated substituents into [1,2,3]Triazolo[1,5-a]pyridines

  摘要：

  [1,2,3]Triazolo[1,5-a]pyridines functionalization with a trifluoromethyl group has been achieved for the first time using different synthetic strategies. Furthermore, these scaffolds have been employed as starting material in the synthesis of new 2,6-disubstituted pyridines containing the trifluoromethyl group, compounds that are not available using other methodologies. A fluorine-mediated triazolopyridine dimerisation is described, improving the previously known synthetic method. Preliminary studies focused on exploring triazolopyridines reactivity with electrophilic fluorine have revealed a new approach for the obtainment of imidazopyridines. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.05.001
• 作为产物：
  描述：

  吡啶-2-甲醛 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-三氟乙酰基吡啶
  参考文献：
  名称：

  可见光活化铱催化的不对称自由基-自由基交叉偶联

  摘要：

  将单电子转移在给体底物和催化剂活化的受体底物之间进行立体控制的自由基-自由基复合，可以由三氟甲基酮和叔胺进行可见光驱动的对映和非对映选择性合成1,2-氨基醇。通过手性铱络合物同时充当路易斯酸和光氧化还原催化剂，可实现高达99％ee的对映选择性 。小于1的量子产率支持了所提出的催化循环，在该催化循环中，由单电子转移介导的每个不对称CC键形成均需要至少一个光子。

  DOI：

  10.1002/anie.201509524

文献信息

• Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
  作者：Xiao-Dong Liu、Hai-Yan Ma、Chun-Hui Xing、Long Lu

  DOI：10.1016/j.cclet.2017.03.031

  日期：2017.8

  cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method

  摘要通过β-三氟甲基-/β-环丙基取代的烯酮与羟胺的DBU促进的多米诺反应，合成了N-三氟甲基和环丙基取代的2-异恶唑啉。多米诺反应由迈克尔加成和随后的环化组成。在温和的反应条件下，以良好或优异的产率获得了广泛的3-取代的5-环丙基-5-三氟甲基-2-异恶唑啉。该方法也可以应用于其他三氟甲基取代的烯酮。
• Oxidation of α-Trifluoromethyl Alcohols Using a Recyclable Oxoammonium Salt
  作者：Christopher B. Kelly、Michael A. Mercadante、Trevor A. Hamlin、Madison H. Fletcher、Nicholas E. Leadbeater

  DOI：10.1021/jo301477s

  日期：2012.9.21

  method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2

  描述了使用氧铵盐4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧铵四氟硼酸（1）将α-三氟甲基醇氧化为三氟甲基酮（TFMK）的简单，温和的方法。在碱性条件下，氧化迅速进行，并提供良好的TFMKs收率，而不会同时形成水合物。氧化的副产物4-乙酰氨基-2,2,6,6-四甲基-1-哌啶基氧基（1c）易于回收，可以方便地再氧化以再生氧代铵盐。
• Catalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-<i>N</i> -hydroxyammonium Cation
  作者：Shelli A. Miller、Kathryn A. Bisset、Nicholas E. Leadbeater、Nicholas A. Eddy

  DOI：10.1002/ejoc.201801718

  日期：2019.2.14

  A hydroxyammonium cation can be used as a catalyst for the fast and easy oxidation of alcohols to aldehydes, ketones, and carboxylic acids.

  羟基铵阳离子可用作将醇快速轻松氧化为醛，酮和羧酸的催化剂。
• Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation
  作者：Christopher B. Kelly、Michael A. Mercadante、Emma R. Carnaghan、Matthew J. Doherty、Diana C. Fager、John J. Hauck、Allyson E. MacInnis、Leon J. Tilley、Nicholas E. Leadbeater

  DOI：10.1002/ejoc.201500565

  日期：2015.7

  homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes.

  公开了一种用于从 α-CF3 高烯丙醇制备三氟甲基取代的乙烯基环丙烷的简单、高产、两步、一锅法。吸电子 CF3 基团对阳离子中间体的不稳定极大地增强了烯烃的相邻基团参与，从而使闭环占主导地位。该反应可以扩展到二氟甲基和五氟乙基，从而能够制备多种氟代烷基取代的乙烯基环丙烷。
• Electroreductive Defluorination of Trifluoromethyl Ketones and Trifluoroacetic Acid Derivatives
  作者：Kenji Uneyama、Go Mizutani、Kazushige Maeda、Tsuyoshi Kato

  DOI：10.1021/jo990571d

  日期：1999.9.1

  Difluoroenol silyl ethers 5 and 6, difluoroketene silyl (O,O-, O,S-, and O,N-) acetals 9 and 21, and 2,2-difluoro-2-trimethylsilylacetates 10 were prepared by electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives in an MeCN-TBAB-chlorotrialkylsilane system using a carbon rod as an anode and a lead plate as a cathode. TBAF- or KF-CuI-promoted alpha-alkylation

  二氟乙烯甲硅烷基醚5和6，二氟乙烯甲硅烷基（O，O-，O，S-和O，N-）乙缩醛9和21和2,2-二氟-2-三甲基甲硅烷基乙酸酯10是通过三氟甲基酮的电还原脱氟制备的MeCN-TBAB-氯三烷基硅烷体系中的三氟乙酸衍生物，其中碳棒为阳极，铅板为阴极。TBAF或KF-CuI促进了用亲电子试剂（如醛，酮，亚胺，酰卤和烷基卤化物）促成的10的α-烷基化反应，从而以良好的收率很好地提供了α-烷基化的α，α-二氟乙酸酯。