4-(N-吗啉)-苯羧酸甲酯 | 23676-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 4-(N-吗啉)-苯羧酸甲酯
• 中文别名: 4-(4-吗啉基)苯甲酸甲酯
• 英文名称: methyl 4-morpholinobenzoate
• 英文别名: N-(4-carbomethoxyphenyl)morpholine；4-morpholin-4-yl-benzoic acid methyl ester；methyl 4-morpholin-4-ylbenzoate
• CAS: 23676-05-3
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD03012127
• 分子量: 221.256
• InChiKey: MMSNLLYQDUZFFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-morpholinobenzoate
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: Methyl 4-morpholinobenzoate
CAS number: 23676-05-3

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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: C12H15NO3
Molecular weight: 221.3

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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.

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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：

  4-(N-吗啉)-苯羧酸甲酯 在 氢氧化钾 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 4-吗啉基苯甲酸
  参考文献：
  名称：

  Study of the microwave-assisted hydrolysis of nitriles and esters and the implementation of this system in rapid microwave-assisted Pd-catalyzed amination

  摘要：

  Microwave-assisted hydrolysis of benzonitriles and methyl benzoates has been studied using a toluene/concd aq KOH two phase system in the presence and absence of phase transfer catalyst. Conditions to allow and avoid smooth hydrolysis could be identified. Based on the latter, the first microwave protocol which allows the rapid Pd-catalyzed amination of aliphatic amines with chlorobenzenes containing sensitive functional groups has been developed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.028
• 作为产物：
  描述：

  对羟基苯甲酸甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) potassium phosphate 、 sodium hydride 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 28.0h， 生成 4-(N-吗啉)-苯羧酸甲酯
  参考文献：
  名称：

  钯催化的芳基壬酸酯的胺化。

  摘要：

  报道了钯催化芳基壬二酸酯的胺化的详细研究。配体2-4和6的使用允许富电子的和-中性的芳基壬酸酯与伯胺和仲胺催化胺化。使用Xantphos 5时，各种功能化的芳基壬酸酯的催化胺化反应可产生优异的苯胺收率。甚至2-羧甲基芳基壬酸酯也可以有效地与伯烷基胺偶联。当将卤代芳基壬酸酯与多种胺偶联时，可获得中等产率，其中在大多数情况下，芳基壬酸酯相对于卤代芳基优先反应。总体而言，在钯催化的CN键形成过程中，壬酸芳基酯是三氟甲磺酸酯的有效替代物，因为它们在反应条件下具有更高的稳定性。

  DOI：

  10.1021/jo034962a

文献信息

• SUBSTITUTED SULFONAMIDE COMPOUNDS
  申请人：OBERBOERSCH Stefan

  公开号：US20080153843A1

  公开（公告）日：2008-06-26

  Substituted sulfonamide derivatives, a process for their preparation, pharmaceutical compositions containing these compounds, and to the use of substituted sulfonamide derivatives in the treatment or inhibition of pain and/or various disorders or disease states.

  磺胺取代物，其制备方法，含有这些化合物的药物组合物，以及磺胺取代物在治疗或抑制疼痛和/或各种疾病或疾病状态中的用途。
• Silver-catalyzed intermolecular amination of fluoroarenes
  作者：Yu Wang、Chenlong Wei、Ruyun Tang、Haosheng Zhan、Jing Lin、Zhenhua Liu、Weihua Tao、Zhongxue Fang

  DOI：10.1039/c8ob01749b

  日期：——

  A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C–F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway

  已经开发了新颖的高选择性的Ag催化的氟代芳烃的分子间胺化。这种转变从容易获得的4-羰基氟苯和NaN 3或其他氮源开始，通过胺化，然后进行CF键断裂，从而在温和的条件下提供所需的4-羰基芳胺产品。用少量水促进反应。该途径不同于先前报道的自由基胺化反应。
• Exhaustive Reduction of Esters Enabled by Nickel Catalysis
  作者：Adam Cook、Sekar Prakash、Yan-Long Zheng、Stephen G. Newman

  DOI：10.1021/jacs.0c02405

  日期：2020.5.6

  tolyl-derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require use of hazardous metal hydrides. Applications in the synthesis of -CD3 containing products, derivatization of bioactive molecules, and chemoselective

  我们报告了将未活化的芳基酯直接还原为其相应的甲苯基衍生物的一步程序。这是通过有机硅烷介导的酯氢化硅烷化反应和随后的 Ni/NHC 催化氢解来实现的。由此产生的条件为通常需要使用危险金属氢化物的这种转化的多步骤程序提供了一种直接有效的替代方法。展示了在合成含 -CD3 的产品、生物活性分子的衍生化以及在其他 CO 键存在下进行化学选择性还原中的应用。
• Triaminophosphine ligands for carbon-nitrogen and carbon-carbon bond formation
  申请人：Iowa State University Research Foundation, Inc.

  公开号：US07385058B1

  公开（公告）日：2008-06-10

  Methods and compounds are provided for the formation of carbon-nitrogen or carbon-carbon bonds comprising reacting an amine or an aryl boronic acid with an aryl halide in the presence of a palladium catalyst, a base, and a compound of formula II:

  方法和化合物用于形成碳氮或碳碳键，包括在钯催化剂、碱和公式II化合物的存在下，将胺或芳基硼酸与芳基卤化物反应。
• A General Palladium-Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
  作者：Pui Ying Choy、Kin Ho Chung、Qingjing Yang、Chau Ming So、Raymond Wai-Yin Sun、Fuk Yee Kwong

  DOI：10.1002/asia.201800575

  日期：2018.9.4

  heterocycles such as indole, carbazole, pyrrole, 10‐phenothiazine, and 10‐phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst

  提出了使用芳基和杂芳基甲苯磺酸盐对各种胺进行单选择性N-芳基化反应的范围和局限性。空气稳定且易于接近的Pd（OAc）2 / CM-phos CM-phos = 2- [2-（二环己基膦基）苯基] -1-甲基-1 H-吲哚}催化剂体系能够处理各种芳基甲苯磺酸酯底物以及胺亲核试剂，包括伯和仲环状/无环脂族胺和苯胺。在这种催化体系下，含NH的杂环如吲哚，咔唑，吡咯，10-吩噻嗪和10-吩恶嗪被证明是可行的偶联伙伴。所描述的反应条件容许宽范围的官能团，并允许从各种酚衍生物容易地获得一系列的芳族胺以及不对称胺产物。有趣的是，该催化剂体系甚至提供了在水介质中进行反应的机会。我们还报道了旋光性α-中心手性胺与芳基甲苯磺酸盐的分子间偶联，而没有削弱对映体的纯度。