1-(邻甲苯基)乙胺 | 42142-17-6

• 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: 1-(邻甲苯基)乙胺
• 中文别名: 1-(2-甲苯基)乙胺；1-邻甲苯乙胺；1-(2-甲基苯基)乙胺
• 英文名称: 1-(o-tolyl)ethanamine
• 英文别名: 1-(o-tolyl)ethan-1-amine；1-(2'-Methylphenyl)Ethylamine；1-(2-Methylphenyl)ethanamine
• CAS: 42142-17-6
• 化学式: C₉H₁₃N
• mdl: MFCD05215232
• 分子量: 135.209
• InChiKey: ZCDYTNZJBGSKFI-UHFFFAOYSA-N

物化性质

• 沸点：
  55-57 °C(Press: 1 Torr)
• 密度：
  0.9736 g/cm3
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(2-Methylphenyl)ethanamine
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: 1-(2-Methylphenyl)ethanamine
CAS number: 42142-17-6

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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: C9H13N
Molecular weight: 135.2

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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.

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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

制备方法与用途

用途

1-(邻甲苯基)乙胺是一种有用的化合物，可用于合成和筛选作为TNF-α抑制剂的macamides类似物。

反应信息

• 作为反应物：
  描述：

  1-(邻甲苯基)乙胺 在 三(五氟苯基)硼烷 、 苯硅烷 作用下， 反应 24.0h， 以93%的产率得到3-乙基甲苯
  参考文献：
  名称：

  B(C6 F5 )3 催化的氢硅烷还原脱氨。

  摘要：

  已知强硼路易斯酸三(五氟苯基)硼烷B(C 6 F 5 ) 3在高温下催化某些胺和氢硅烷的脱氢偶联。在较高温度下，脱氢途径与CN键的断裂竞争并获得去官能化。这可以成为一种有用的方法，用于多种胺以及异氰酸酯和异硫氰酸酯等杂积烯的无过渡金属还原脱氨。

  DOI：

  10.1002/anie.202004651
• 作为产物：
  描述：

  1-(2-methylphenyl)ethan-1-imine 在 乙醇 、 铂 作用下， 生成 1-(邻甲苯基)乙胺
  参考文献：
  名称：

  Ketimines. VI. o-Tolyl Alkyl Ketimines¹

  摘要：

  DOI：

  10.1021/ja01119a035
• 作为试剂：
  描述：

  四氢呋喃 、 乙醚 、 溴乙酸乙酯 在 三乙胺 作用下， 以 1-(邻甲苯基)乙胺 为溶剂， 生成 N-(Ethoxycarbonylmethyl)-1-(2'-Methylphenyl)Ethylamine
  参考文献：
  名称：

  Quinazoline deriviates for treating peptic ulcer

  摘要：

  化学式（I）表示的喹唑啉衍生物或其药用盐可用于治疗消化性溃疡，其中：##STR1## R.sub.1和R.sub.2分别为氢或C.sub.1-C.sub.4烷基；R.sub.3为氢或卤素；R.sub.4、R.sub.5、R.sub.6、R.sub.7、R.sub.8和R.sub.9，可以相同也可以不同，分别为氢、C.sub.1-C.sub.4烷基、环丙基或带有卤素的C.sub.1-C.sub.4烷基；R.sub.10为甲氧基。

  公开号：

  US05686458A1

文献信息

• Halo sulfonyl aryl boronates
  申请人：——

  公开号：US20040116701A1

  公开（公告）日：2004-06-17

  The present invention relates to halo sulfonyl aryl boronates of the general formula (I): 1 wherein Arylene designates a carbocyclic or heterocyclic, aromatic ring system comprising 1-3 rings; R 1 , R 2 and R 3 are, independently, hydrogen, C 1-6 alkyl, C 1-6 alkoxy, halogen, nitro, cyano or phenyl; X is fluoro, chloro or bromo; and Y is a boroxine moiety attached via a bond from Arylene to one of the boron atoms of a boroxine ring which ring has a group of the formula—Arylene(R 1 )(R 2 )(R 3 )SO 2 X, wherein Arylene, R 1 , R 2 , R 3 and X are as defined above, at each of the other two boron atoms of the boroxine ring, or Y is a boronic acid group or a boronic ester group. The invention also relates to the preparation of the compounds of formula (I) and to their use in organic synthesis.

  本发明涉及一般式（I）的卤磺酰基芳基硼酸酯： 其中Arylene表示一个含有1-3个环的碳环或杂环芳香环系统； R1、R2和R3分别为氢、C1-6烷基、C1-6烷氧基、卤素、硝基、氰基或苯基； X为氟、氯或溴；以及 Y是通过一条键连接到Arylene上的硼氧杂环基，该环具有一个式为Arylene(R1)(R2)(R3)SO2X的基团，在硼氧杂环的另外两个硼原子上，或Y是硼酸基团或硼酯基团。 该发明还涉及一般式（I）化合物的制备以及它们在有机合成中的应用。
• Binding-Site Compatible Fragment Growing Applied to the Design of β₂-Adrenergic Receptor Ligands
  作者：Florent Chevillard、Helena Rimmer、Cecilia Betti、Els Pardon、Steven Ballet、Niek van Hilten、Jan Steyaert、Wibke E. Diederich、Peter Kolb

  DOI：10.1021/acs.jmedchem.7b01558

  日期：2018.2.8

  neglected. In this study we computationally extended, chemically synthesized, and experimentally assayed new ligands for the β2-adrenergic receptor (β2AR) by growing fragment-sized ligands. In order to address the synthetic tractability issue, our in silico workflow aims at derivatized products based on robust organic reactions. The study started from the predicted binding modes of five fragments. We suggested

  基于片段的药物发现与片段扩展方法密切相关，可以使用从头设计软件加速片段扩展方法。尽管计算机允许轻松生成数以百万计的建议，但综合可行性却经常被忽略。在这项研究中，我们计算延长，化学合成，和实验测定的β新配体2肾上腺素能受体（β 2AR）通过增加片段大小的配体来实现。为了解决合成易处理性问题，我们的计算机模拟工作流程旨在基于稳健的有机反应衍生化产品。该研究从五个片段的预测结合模式开始。我们提出了总共八种易于合成的不同延伸序列，进一步的分析表明，与它们各自的初始片段相比，四种产物具有更高的亲和力（最高40倍）。所描述的工作流程（我们称其为“通过合并增长”）及其关键工具可在线使用，可以改进基于片段的早期药物发现项目，使其成为药物化学家在结构与活性关系（SAR）研究期间有用的创新工具。
• Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid
  作者：Ga Lee、Myung Hyun

  DOI：10.3390/molecules191221386

  日期：——

  analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS) of 1.55 when a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline

  芬迪林是一种有效的抗心绞痛治疗冠心病的药物，其十六种类似物在基于（+）-（18-crown-6）-2,3,11,12-四羧酸的CSP上拆分。当流动相由比例为80/20 / 0.1 / 0.5（v / v）的甲醇-乙腈-三氟乙酸-三乙胺组成的流动相时，芬迪林的分离度（α）为1.25，分离度（RS）为1.55 / v / v）。色谱分析法比较了芬迪林及其类似物的拆分行为，表明与芬迪林仲氨基键合的3,3-二苯丙基在手性识别中很重要，而苯基与苯丙氨酸之间的空间体积差异也很重要。芬迪林手性中心的甲基在手性识别中也很重要。
• Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines
  作者：Thomas C. Nugent、Daniela E. Negru、Mohamed El-Shazly、Dan Hu、Abdul Sadiq、Ahtaram Bibi、M. Naveed Umar

  DOI：10.1002/adsc.201100250

  日期：2011.8

  Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethy

  以良好至高产率并且形成难以访问手性伯胺EE使用一锅合成从前手性酮的一个罕见的例子（顺序还原性胺化-hydrogenloysis）。作为亮点，我们还证明了邻甲氧基苯乙酮的一锅还原胺化-氢解还原还原胺化（五个反应）产生了手性二胺1-（2-甲氧基苯基）乙基-（2-吡啶基甲基）-胺（4）（ 58％的总收率，> 99％ee），这是一种用于水性对映选择性羟醛反应的新型有机催化剂。
• The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst
  作者：Christoph Bäumler、Christof Bauer、Rhett Kempe

  DOI：10.1002/cssc.202000856

  日期：2020.6.19

  The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth‐abundant metals is similarly appealing. Here, the iron‐catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed

  氨将酮和醛还原胺化是合成伯胺的极具吸引力的方法。同样，使用基于富含地球的金属的催化剂，尤其是可重复使用的催化剂也具有吸引力。在此，通过还原胺化实现了铁催化的伯胺合成。观察到广泛的范围和对官能团的很好的耐受性。酮，包括纯脂肪族的酮，芳基-烷基，二烷基和杂环，以及醛，可以平稳地转化为其相应的伯胺。此外，还演示了胺化药物，生物活性化合物和天然产物。可以容忍许多官能团，例如羟基，甲氧基，二恶唑，磺酰基和硼酸酯取代基。催化剂易于操作，选择性，可重复利用，氨水可作为氮源。关键是使用特定的Fe络合物进行催化剂合成，并使用N掺杂SiC材料作为催化剂载体。