5-氰基-2-甲氧基-苯胺 | 60979-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-氰基-2-甲氧基-苯胺
• 中文别名: 3-氨基-4-甲氧基苯甲腈；3-氨基-4-甲氧基苯腈
• 英文名称: 3-amino-4-methoxybenzonitrile
• CAS: 60979-25-1
• 化学式: C₈H₈N₂O
• mdl: MFCD09745274
• 分子量: 148.164
• InChiKey: MAYBZGKWHOVSAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  332.8±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-4-methoxybenzonitrile
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-Amino-4-methoxybenzonitrile
CAS number: 60979-25-1

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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: C8H8N2O
Molecular weight: 148.2

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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

反应信息

• 作为反应物：
  描述：

  5-氰基-2-甲氧基-苯胺 在 silica gel supported sulfuric acid 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以83%的产率得到3-氨基-4-甲氧基苯甲酰胺
  参考文献：
  名称：

  二氧化硅-硫酸：用于将腈水合为酰胺的新型、简单、高效且可重复使用的催化剂

  摘要：

  腈水合成相应的酰胺在有机化学和化学工业中非常重要。这种转换有许多不同的方法。腈水合是一种经典的转变，但即使使用范围广泛的可用试剂，仍然难以实现。传统上，使用各种酸或碱作为催化剂[1-9]。使用 Co [10,11]、Mo [12]、Ru [13-16]、Rh [17,18]、Pd [19,20]、Ir [21] 和 Pt [22- 24]。均相金属催化经常用于工业环境。亲密的催化剂底物相互作用、温和的反应条件和对催化过程的理解被认为是主要优点。腈 (RCN) 催化水合为甲酰胺 (RCONH2) 代表了在实验室和工业环境中获得这些产品的基本重要途径 [25-34]。由于 Yamaguchi 等人发现氧化铝负载的氢氧化钌催化剂 [Ru(OH)x/Al2O3]。[15] 固体负载的钌已成为腈水合的一类重要催化剂，表现出对甲酰胺形成的高选择性以及其他实际优势 [35-50]。尽管 RuCl3·nH2O

  DOI：

  10.14233/ajchem.2016.19907
• 作为产物：
  描述：

  4-甲氧基苯甲腈 在 O-新戊酰羟铵三氟甲磺酸盐 、 copper(II) oxide 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以59 %的产率得到5-氰基-2-甲氧基-苯胺
  参考文献：
  名称：

  铜催化芳烃CH键与羟胺衍生物的伯胺化

  摘要：

  开发了一种利用羟胺衍生物作为氨替代物对芳香族 C(sp 2 )-H 键进行伯胺化的新方法。利用经济高效且方便的氧化铜，在温和条件下无需外部氧化剂即可合成多种芳香伯胺，且收率中等至良好。这种胺化表现出优异的官能团耐受性、广泛的底物范围、使用现成的底物以及简便的后处理程序。此外，还允许对结构复杂的类药小分子进行后期修饰。

  DOI：

  10.1016/j.tetlet.2023.154699

文献信息

• CHROMENONE DERIVATIVES
  申请人：BARLAAM Bernard Christophe

  公开号：US20110098271A1

  公开（公告）日：2011-04-28

  The invention concerns chromenone derivatives of Formula I or a pharmaceutically-acceptable salts thereof, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , n and R 9 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

  这项发明涉及公式I的香豆素衍生物或其药用盐，其中R1、R2、R3、R4、R5、R6、R7、R8、n和R9中的每一个具有在描述中定义的任何含义；它们的制备方法，含有它们的药物组合物以及它们在制造用于治疗细胞增殖紊乱的药物的药物中的使用。
• Direct and Practical Synthesis of Primary Anilines through Iron-Catalyzed C–H Bond Amination
  作者：Luca Legnani、Gabriele Prina Cerai、Bill Morandi

  DOI：10.1021/acscatal.6b02576

  日期：2016.12.2

  The direct C–H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C–H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves

  芳烃的直接C–H胺化是简化功能分子的发现和制备的重要策略。在本文中，我们报道了一种操作简单的芳烃CH胺化反应，与大多数文献先例相反，该反应直接提供了合成通用的伯胺产品，而无需依赖于保护基团的操纵。廉价的硫酸铁（II）可作为转化的方便催化剂。该反应可耐受多种芳烃，包括结构复杂的药物。重要的是，芳烃底物在转化中用作限制性试剂。这种操作上简单的转变将大大加快药物和功能分子的发现。
• [EN] CHROMENONE DERIVATIVES WITH ANTI-TUMOUR ACTIVITY<br/>[FR] DÉRIVÉS DE CHROMÉNONE À ACTIVITÉ ANTITUMORALE
  申请人：ASTRAZENECA AB

  公开号：WO2011051704A1

  公开（公告）日：2011-05-05

  The invention concerns chromenone derivatives of Formula (I) or a pharmaceutically-acceptable salts thereof, wherein each of R1, R2, R3, R4, R5, R6, R7, R8, n and R9 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

  这项发明涉及公式（I）的香豆素衍生物或其药用盐，其中R1、R2、R3、R4、R5、R6、R7、R8、n和R9中的每一个具有在描述中先前定义的任何含义；它们的制备方法，含有它们的药物组合物以及它们在制造用于治疗细胞增殖紊乱的药物的药物中的使用。
• Photocatalytic C–H Amination of Aromatics Overcoming Redox Potential Limitations
  作者：Tatsuya Morofuji、Gun Ikarashi、Naokazu Kano

  DOI：10.1021/acs.orglett.0c00822

  日期：2020.4.3

  report the photocatalytic C–H amination of aromatics overcoming redox potential limitations. Radical cations of aromatic compounds are generated photocatalytically using Ru(phen)3(PF6)2, which has a reduction potential at a high oxidation state (Ered(RuIII/RuII) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates (Eox = +1.65 to +2.27 V vs SCE). The radical cations are trapped

  我们报道了克服氧化还原潜在限制的芳香族化合物的光催化C–H胺化反应。使用Ru（phen）3（PF 6）2光催化生成芳香族化合物的自由基阳离子，该Ru（phen）3（PF 6）2在高氧化态下的还原电势（E red（Ru III / Ru II）= +1.37 V vs SCE）低于三氧化二砷。芳香族底物的氧化电位（E ox = +1.65至+2.27 V vs SCE）。自由基阳离子被吡啶捕获，得到N-芳基吡啶鎓离子，该离子被转化为芳族胺。
• Benzopyran derivatives
  申请人：Recordati, S.A. Chemical and Pharmaceutical Company

  公开号：US06403594B1

  公开（公告）日：2002-06-11

  The invention relates to novel benzopyran derivatives of formula I, their N-oxides and pharmaceutically acceptable salts thereof. The compounds are endowed with enhanced selectivity for alpha1-adrenergic receptors and a low activity in lowering blood pressure. The compounds are useful in the treatment of obstructive syndromes of the lower urinary tract, including benign prostatic hyperplasia (BPH), and in the treatment of lower urinary tract symptoms (LUTS), neurogenic lower urinary tract dysfunction (NLUTD), and other conditions.

  该发明涉及公式I的新型苯并吡喃衍生物，它们的N-氧化物及其药用可接受的盐。这些化合物具有增强的α1-肾上腺素受体选择性和降低血压活性较低。这些化合物在治疗下尿路梗阻综合症，包括良性前列腺增生（BPH），以及治疗下尿路症状（LUTS），神经源性下尿路功能障碍（NLUTD）和其他疾病方面是有用的。