(2-氟苯基)-吗啉-4-甲酮 | 1978-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-氟苯基)-吗啉-4-甲酮
• 英文名称: (2-fluorophenyl)(morpholino)methanone
• 英文别名: 4-(2-fluorobenzoyl)-morpholine；N-(2-Fluorobenzoyl)morpholine；(2-fluorophenyl)-morpholin-4-ylmethanone
• CAS: 1978-64-9
• 化学式: C₁₁H₁₂FNO₂
• mdl: MFCD00120209
• 分子量: 209.22
• InChiKey: OIDNOKLCLGRXCW-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  350.3±37.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)
• 溶解度：
  >31.4 [ug/mL]
• 保留指数：
  1695

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-(2-Fluorobenzoyl)morpholine
Synonyms: (2-Fluorophenyl)(morpholino)methanone

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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: N-(2-Fluorobenzoyl)morpholine
CAS number: 1978-64-9

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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: C11H12FNO2
Molecular weight: 209.2

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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-氟苯基)-吗啉-4-甲酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 (2-fluorophenyl)(morpholino)methanethione
  参考文献：
  名称：

  An efficient route to 3-aminoindazoles and 3-amino-7-azaindazoles

  摘要：

  A non-acidic procedure for the preparation of 3-aminoindazoles and 3-amino-7-azaindazoles from 2-fluoroaryl carboxylic acids is reported. The synthesis starts from readily available starting materials and uses mild and practical reaction conditions in a three-step overall procedure. Products were isolated for a number of examples, but yields varied significantly depending on electronic nature of the substituents. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.100
• 作为产物：
  描述：

  4-苯甲酰吗啉 在 silver nitrate 、 N-氟代双苯磺酰胺 、 palladium dichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以56%的产率得到(2-氟苯基)-吗啉-4-甲酮
  参考文献：
  名称：

  硝酸盐促进的苯甲酰胺和苯乙酰胺的选择性C–H氟化

  摘要：

  利用各种弱配位酰胺作为内在的指导基团，开发了一种通用的，选择性的硝酸盐促进的CH键氟化方法。不同的叔和仲酰胺经过选择性的芳族C–H键氟化，具有宽范围的底物范围，良好的区域选择性和温和的条件。此外，首次报道了通过远端定向对具有挑战性的苯乙酰胺进行后期的C–H键氟化。

  DOI：

  10.1021/acs.orglett.8b00793

文献信息

• Ortho lithiation-in situ borylation of substituted morpholine benzamides
  作者：Anna Cederbalk、Morten Lysén、Jan Kehler、Jesper L. Kristensen

  DOI：10.1016/j.tet.2017.02.002

  日期：2017.3

  Morpholine amides are cheap and safe alternative to Weinreb amides as acylating agents of organometallic species. Herein, the in-situ lithiation/borylation of 18 ortho- meta- and para-substituted morpholine benzamides has been investigated. 10 of the 18 substrates provided the desired boronic esters as the major isomer (>90% regioselectivity) in crude isolated yields ranging from 68 to 93%. The synthetic

  吗啉酰胺是Weinreb酰胺作为有机金属物种酰化剂的廉价且安全的替代品。在此，已经研究了18种邻位间和对位取代的吗啉苯甲酰胺的原位锂化/硼化。18种底物中的10种提供了所需的硼酸酯作为主要异构体（> 90％的区域选择性），分离出的粗品收率为68％至93％。随后通过激酶抑制剂的合成说明了此类构件的合成可用性。
• Organophotoredox‐Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol
  作者：Sk. Sheriff Shah、Maniklal Shee、Yarra Venkatesh、Amit Kumar Singh、Samya Samanta、N. D. Pradeep Singh

  DOI：10.1002/chem.201904924

  日期：2020.3.23

  formations. The hydrogen-bonded OH group activated the adjacent C-H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C-H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which

  有机光催化剂[4CzIPN（1,2,3,5-四（咔唑-9-基）-4,6二氰基苯）或5MeOCzBN（2,3,4,5,6-戊基（3,6- [二甲氧基-9 H-咔唑-9-基）苄腈]，喹啉和磷酸四正丁铵（氢键催化剂）用于酰胺键的形成。氢键合的OH基团通过自由基将醇的相邻CH键朝着氢原子转移（HAT）活化。通过光催化剂对奎尼丁进行单电子氧化而生成的奎尼丁鎓自由基阳离子，由于极性效应产生的α-羟烷基自由基选择性地从醇的α-CH键中提取氢原子，随后转化为相应的在有氧条件下的醛。
• Organic ligand-free carbonylation reactions with unsupported bulk Pd as catalyst
  作者：Shujuan Liu、Hongli Wang、Xingchao Dai、Feng Shi

  DOI：10.1039/c8gc00740c

  日期：——

  ligand-free conditions, namely, hydroaminocarbonylation of olefins, aminocarbonylation of aryl iodides and oxidative carbonylation of amines, which almost cover all the known mechanisms in carbonylation reactions. Notably, the bulk Pd catalyst system exhibited better catalytic activity than the classical homogeneous PdCl2/(2-OMePh)3P catalyst system. This study will create a momentous and new field of green

  在此，给出了大量的Pd催化的羰基化反应的令人惊讶的结果。在无有机配体的条件下可以有效地实现三种类型的羰基化反应，即烯烃的氢氨基羰基化，芳基碘化物的氨基羰基化和胺的氧化羰基化，这几乎涵盖了羰基化反应中的所有已知机理。值得注意的是，本体Pd催化剂体系表现出比经典的均相PdCl 2 /（2-OMePh）3 P催化剂体系更好的催化活性。这项研究将为绿色羰基化反应创造一个重要的新领域。
• 一种合成2-氟代-N-取代芳基甲酰胺类化合 物的方法
  申请人：浙江工业大学

  公开号：CN108503501B

  公开（公告）日：2021-09-21

  本发明提供了一种合成2‑氟代‑N取代芳基甲酰胺类化合物的方法，所述的方法为：N‑取代芳基甲酰胺类化合物在钯催化剂、氟化试剂和添加剂存在的条件下，在20～150℃下进行反应，TLC跟踪检测至反应完全，经过后处理得到式II所示的化合物，温和地实现酰胺取代基邻位高选择性的芳基碳氢键直接氟化。本发明的方法具有反应条件温和、操作简单、底物适应性好、氟化选择性高等优点，具有较高的应用研究价值。
• Mechanochemical Pd-Catalyzed Amino- and Oxycarbonylations using FeBr₂(CO)₄ as a CO Source
  作者：Tomáš Čarný、Péter Kisszékelyi、Martin Markovič、Tibor Gracza、Peter Koóš、Radovan Šebesta

  DOI：10.1021/acs.orglett.3c03440

  日期：2023.12.8

  Herein, we describe the development of mechanochemical amino- and oxycarbonylation employing FeBr2(CO)4 as a solid CO source. This Pd/XantPhos-catalyzed reaction affords a range of carboxamides and esters from aryl iodides and various amines or phenols. Both primary and secondary amines, including amino acids, can be employed as N-nucleophiles.

  在此，我们描述了使用 FeBr 2 (CO) 4作为固体 CO 源的机械化学氨基和氧羰基化的发展。这种 Pd/XantPhos 催化的反应由芳基碘化物和各种胺或酚生成一系列甲酰胺和酯。伯胺和仲胺，包括氨基酸，都可以用作N-亲核试剂。