3-氟苯甲酰乙腈 | 21667-61-8

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯腈系列
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氟苯甲酰乙腈
• 中文别名: 3-氟苯甲酰基乙腈；3-(3-氟苯基)-3-氧代丙腈
• 英文名称: 3-fluorobenzoylacetonitrile
• 英文别名: 3-(3-fluorophenyl)-3-oxopropanenitrile；3-Fluor-benzoylacetonitril；(m-fluorobenzoyl)-acetonitrile
• CAS: 21667-61-8
• 化学式: C₉H₆FNO
• mdl: MFCD02260777
• 分子量: 163.151
• InChiKey: UNGFCWRGMBVFAS-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  304.4±22.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  丙酮（少量溶解）、氯仿（少量溶解）、甲醇（极少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluorobenzoylacetonitrile
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-Fluorobenzoylacetonitrile
CAS number: 21667-61-8

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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: C9H6FNO
Molecular weight: 163.1

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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-氟苯甲酰乙腈 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  一种含氮、硫的稠环化合物的制备方法及应用

  摘要：

  本发明提供了一种含氮、硫的稠环化合物的制备方法及应用。本发明合成方法具有产率高、时间短、操作简单等优点，并且使用普通廉价的试剂，降低制备的成本，易于推广应用。基于含氮、硫的稠环化合物可在有机电致发光、有机场效应管、有机二阶非线性、手性液晶以及生物医药等领域得到应用。

  公开号：

  CN108623613A
• 作为产物：
  描述：

  3'-氟苯乙酮 在 溴 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 3-氟苯甲酰乙腈
  参考文献：
  名称：

  3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors

  摘要：

  The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory potency. Especially the important finding is that 5-(2,5-dichloro)phenyl and 5-(2-methoxy-5-chloro)phenyl derivatives exhibit high NHE-1 inhibitory activities (IC50 < 0.02 microM) that match those of 3-unsubstituted derivatives.

  DOI：

  10.1016/j.bmcl.2006.12.012

文献信息

• Rh(III)-Catalyzed C–H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo[<i>de</i>]chromenes
  作者：Feifei Fang、Chunmei Zhang、Chaofan Zhou、Yazhou Li、Yu Zhou、Hong Liu

  DOI：10.1021/acs.orglett.8b00103

  日期：2018.4.6

  Rh (III)-catalyzed C–H activation of benzoylacetonitriles in coupling with diazo compounds was developed to synthesize diversified substituted benzo[de]chromenes via a formal (4 + 2) cycloaddition with a diazo compound and subsequent tandem (4 + 2) cycloaddition with another diazo compound. Intriguingly, synthesis of substituted benzo[de]chromenes and their decarboxylation products could be realized

  Rh（III）催化与重氮化合物偶合的苯甲酰基乙腈的C–H活化反应是通过与重氮化合物的正式（4 + 2）环加成反应和随后的串联（4 + 2）环加成反应，合成出多种取代的苯并[ de ]色烯。与另一种重氮化合物。有趣的是，通过控制反应条件，可以实现取代苯并[ de ]二甲基苯酮及其脱羧产物的合成。这些反应具有广泛的底物范围，中等至良好的产率，以及较高的区域选择性。
• Formal [3+2] Annulation of Copper‐Allenylidenes with 3‐Oxo‐3‐Arylpropanenitriles: Synthesis of Tetrasubstituted Furans
  作者：De Zhong、Feng Jiang、Siyong Shen、Lan Wang、Wei Wang、Yongjun Wu、Yumei Xiao、Hongchao Guo

  DOI：10.1002/adsc.202000929

  日期：2020.11.18

  The copper‐catalyzed decarboxylative [3+2] annulation of ethynyl benzoxazinanones with 3‐oxo‐3‐arylpropanenitriles has been developed, producing tetrasubstituted furan derivatives in moderate to high yield. This reaction was generally compatible with a wide range of substrates. Notably, the intermediate copper‐allenylidenes worked as a C2 synthon in the cycloaddition reaction.

  已开发出铜催化的乙炔基苯并恶嗪酮与3-氧代-3-芳基丙腈的[3 + 2]环化反应，可中等至高收率生产四取代呋喃衍生物。该反应通常与多种底物相容。值得注意的是，中间体铜-亚烯基铜在环加成反应中充当C2合成子。
• Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
  作者：Ge Zeng、Jichao Liu、Yinlin Shao、Fangjun Zhang、Zhongyan Chen、Ningning Lv、Jiuxi Chen、Renhao Li

  DOI：10.1021/acs.joc.0c02388

  日期：2021.1.1

  A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures

  已经开发出一种实用，方便且高度选择性的方法，该方法是由Pd催化的向二腈中添加有机硼试剂而合成β-酮腈。该方法提供了优异的官能团耐受性，广泛的基材范围以及使用市售基材的便利性。该方法有望在未来的合成程序中显示出更多的实用性。
• [EN] ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR INHIBITORS<br/>[FR] INHIBITEURS DE RÉCEPTEURS NICOTINIQUES ALPHA-7 DE L'ACÉTYLCHOLINE
  申请人：WYETH CORP

  公开号：WO2010009290A1

  公开（公告）日：2010-01-21

  The present invention provides compounds and compositions, methods of making them, and methods of using them to modulate α7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory systems.

  本发明提供了化合物和组合物，制备它们的方法，以及利用它们调节α7烟碱乙酰胆碱受体和/或治疗各种疾病、疾病和症状的方法。所提供的化合物可以影响神经系统、精神病学和/或炎症系统等方面。
• A ‘sulfonyl-azide-free’ (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
  作者：Dmitry Dar’in、Grigory Kantin、Mikhail Krasavin

  DOI：10.1039/c9cc02042j

  日期：——

  Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first ‘sulfonyl-azide-free’ (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution

  众所周知，重氮转移反应与潜在爆炸性磺酰叠氮化物的使用有关。研发了第一个通过Regitz重氮转移反应从其活性亚甲基前体生产重氮化合物的“无磺酰叠氮”（SAFE）方案，该方案已显示出显着的底物范围。它可用于产生重氮化合物的阵列，以通过组合化学和一系列支架产生的转化进一步进化。