N-甲基联苯-2-胺 | 14925-09-8

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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: N-甲基联苯-2-胺
• 英文名称: 2-(N-methylamino)-1,1'-biphenyl
• 英文别名: 2-methylaminobiphenyl；N-methyl-[1,1'-biphenyl]-2-amine；N-methylbiphenyl-2-amine；biphenyl-2-yl-methylamine；N-methyl-2-phenylaniline
• CAS: 14925-09-8
• 化学式: C₁₃H₁₃N
• mdl: MFCD00179576
• 分子量: 183.253
• InChiKey: CARILLOXVAEKID-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±21.0 °C(Predicted)
• 密度：
  1.052

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  12
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Methylbiphenyl-2-amine
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: N-Methylbiphenyl-2-amine
CAS number: 14925-09-8

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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: C13H13N
Molecular weight: 183.3

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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：

  N-甲基联苯-2-胺 在 aluminum (III) chloride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5,7-二氢-5-甲基-6H-二苯并[b,d]氮杂卓-6-酮
  参考文献：
  名称：

  New Flurbiprofen Derivatives: Synthesis, Membrane Affinity and Evaluation of in Vitro Effect on β-Amyloid Levels

  摘要：

  阿尔茨海默病（AD）的特征是不可逆的、渐进性的记忆和认知丧失以及显著的神经细胞损失。目前针对阿尔茨海默病的治疗策略主要针对多种靶点，旨在逆转或预防疾病，但不幸的是，现有的治疗往往没有显著的临床益处。在过去的几十年里，抑制或调节γ-分泌酶、减少β淀粉样蛋白（Aβ）水平的化合物被认为是阿尔茨海默病的潜在治疗方案。在这些化合物中，氟比洛芬（FLU）的(R)-对映体似乎非常有前途，但其脑部渗透性较低。在本研究中，为了改善FLU在阿尔茨海默病发病机制中的作用，我们合成了一些新型的FLU脂溶性类似物。新分子的脂溶性通过clogP、log KC18/W和log K IAM/W值进行了表征。其通透性在不同pH值的胃肠道PAMPA（PAMPA-GI）和脑血屏障PAMPA（PAMPA-BBB）模型中进行了测定。它们还被测试了抑制大鼠CTXTNA2星形胶质细胞体外γ-分泌酶活性的能力。有趣的是，研究的分子显示出能够在明确的浓度依赖性方式下降低Aβ 42水平，而不影响淀粉样前体蛋白APP的水平。

  DOI：

  10.3390/molecules180910747
• 作为产物：
  描述：

  乙基联苯-2-基氨基甲酸酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-甲基联苯-2-胺
  参考文献：
  名称：

  Novel phosphinine compounds and metal complexes thereof

  摘要：

  式(I)的膦烯可以与金属盐结合以制备氢甲酰化催化剂。膦烯配合物具有两个磷中心，可以用各种杂原子或烷基取代物替换，以改变膦烯的配体特性。膦烯金属配合物在正常的氢甲酰化反应条件下被使用。式(I)的膦烯配体的制备途径允许进行方便的合成。

  公开号：

  US20020103375A1

文献信息

• Palladium‐Catalyzed Methylation of Nitroarenes with Methanol
  作者：Lin Wang、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201814146

  日期：2019.4.8

  procedure for the synthesis of N‐methyl‐arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1‐[2,6‐bis(isopropyl)phenyl]‐2‐[tert‐butyl(2‐pyridinyl)phosphino]‐1H‐Imidazole (L1). The generality of this protocol is demonstrated in the synthesis of more than 20

  开发了使用甲醇作为绿色甲基化剂直接从硝基芳烃合成N-甲基-芳基胺的方法。成功的关键是使用由乙酸钯和配位体的1- [2,6-双（异丙基）苯基] -2- [叔-丁基（2-吡啶基）膦基] -1的特定催化剂体系的ħ -咪唑（L1）。在相对温和的条件下合成20多种N-甲基-芳基胺证明了该方案的普遍性。将这种新颖的方法与使用相同催化剂的后续偶联工艺相结合，可以使芳香族硝基化合物有效地分散为包括药物分子在内的各种胺类。
• Reductive C(sp²)–N Elimination from Isolated Pd(IV) Amido Aryl Complexes Prepared Using H₂O₂ as Oxidant
  作者：Elikplim Abada、Peter Y. Zavalij、Andrei N. Vedernikov

  DOI：10.1021/jacs.6b12648

  日期：2017.1.18

  ketone (dpk)-supported amidoarylpallada(II)cycles derived from various 2-(N-R-amino)biphenyls (R = H, Me, CF3CO, MeSO2, CF3SO2) react with hydrogen peroxide in MeOH, THF, MeCN or AcOH to form the corresponding C-N coupled products, N-R-substituted carbazoles, in 82-98% yield. For R = MeSO2 and CF3SO2, the corresponding reaction intermediates, amidoaryl Pd(IV) complexes were isolated and characterized by

  衍生自各种 2-(NR-氨基) 联苯 (R = H, Me, CF3CO, MeSO2, CF3SO2) 的二-2-吡啶基酮 (dpk) 支持的酰胺芳基钯 (II) 环与过氧化氢在 MeOH、THF、MeCN 中反应或 AcOH 形成相应的 CN 偶联产物，NR 取代的咔唑，产率为 82-98%。对于 R = MeSO2 和 CF3SO2，相应的反应中间体，酰胺芳基 Pd(IV) 配合物被分离出来，并通过单晶 X 射线衍射和/或核磁共振光谱进行表征。首次详细研究了从分离的酰胺芳基 Pd(IV) 配合物中的 C(sp2)-N 还原消除。
• Visible-light-mediated selective thiocyanation/ipso-cyclization/oxidation cascade for the synthesis of thiocyanato-containing azaspirotrienediones
  作者：Yuan Chen、Yu-Jue Chen、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2019.130763

  日期：2019.12

  visible-light-mediated metal-free thiocyanate radical addition/ipso-cyclization/oxidation cascade reaction for the synthesis of thiocyanato-containing azaspirotrienediones from N-phenylpropynamides is described. Cheap and readily available ammonium thiocyanate was used as a precursor to the thiocyanate free radical, which undergoes a radical addition reaction with the alkyne, followed by selective ipso-cyclization

  可见光介导的不含金属的硫氰酸盐基加/本位-cyclization /氧化级联含氰硫基azaspirotrienediones的从合成反应Ñ -phenylpropynamides进行说明。便宜和容易获得的硫氰酸铵用作前体硫氰酸自由基，其经历与炔自由基加成反应，然后进行选择性本位-cyclization和氧化，得到脱芳构化产品。没有检测到邻环化的产物。该反应在一锅中完成了C–S，CC和C = O键的合成，其中大量和可再生的空气氧气是唯一的牺牲试剂和氧气源。
• Highly Selective N-Monomethylanilines Synthesis From Nitroarene and Formaldehyde via Kinetically Excluding of the Thermodynamically Favorable N,N-Dimethylation Reaction
  作者：Hongli Wang、Hangkong Yuan、Benqun Yang、Xingchao Dai、Shan Xu、Feng Shi

  DOI：10.1021/acscatal.8b00116

  日期：2018.5.4

  The synthesis of N-monomethylamine remains a challenging topic because the N,N-dimethylation reaction is thermodynamically favorable. In this work, the kinetically controlled N-monomethylamine synthesis from nitroarene and paraformaldehyde/H2 is reported to have superhigh N-monomethylamine selectivity in the presence of a Pd/TiO2 catalyst. The superior selectivity should be attributed to the preferential

  N-单甲胺的合成仍然是一个具有挑战性的课题，因为N，N-二甲基化反应在热力学上是有利的。在这项工作中，据报道，在Pd / TiO 2催化剂存在下，由硝基芳烃和多聚甲醛/ H 2进行动力学控制的N-单甲胺合成具有超高的N-单甲胺选择性。如NH 3 / Me 2 NH-TPD所表明的那样，较高的选择性应归因于Pd / TiO 2表面伯胺优先于N-单甲胺的吸附，而优良的催化活性可能与良好的H有关。2 NH阐明的催化剂的活化能力和高胺吸附能力3 -TPD和H 2 -TPR测试。以含有甲基，甲氧基，羟基，氟化物，三氟甲基，酯和酰胺取代基的各种硝基芳烃为起始原料，均获得了良好的结果，该方法在药物中的潜在合成效用通过药物分子的N-单甲基化来说明，例如如clinidipine，尼美舒利，普鲁卡因和氨基水杨酸甲酯。
• [EN] TASK CHANNEL ANTAGONISTS<br/>[FR] ANTAGONISTES DES CANAUX TASK
  申请人：MERCK SHARP & DOHME

  公开号：WO2011106276A1

  公开（公告）日：2011-09-01

  This invention relates to TASK-1 and/or TASK-3 antagonists and/or their pharmaceutically acceptable salts, compositions and methods for treating and preventing disorders which are caused by activation or by an activated TASK-1 and/or TASK-3, and disorders which have TASK-1 and/or TASK-3-related damage as a secondary cause.

  这项发明涉及TASK-1和/或TASK-3拮抗剂及/或其药用盐、用于治疗和预防由TASK-1和/或TASK-3的激活或被激活引起的疾病，以及由TASK-1和/或TASK-3相关损伤作为次要原因的疾病的组合物和方法。