N-乙酰基-2-溴-4-甲氧基苯胺 | 79069-37-7

• 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-乙酰基-2-溴-4-甲氧基苯胺
• 中文别名: N-乙酰基2-溴-4-甲氧基苯胺
• 英文名称: N-(2-bromo-4-methoxyphenyl)acetamide
• CAS: 79069-37-7
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: AXORYKRDGLYSCK-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  376.0±32.0 °C(Predicted)
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Acetyl 2-bromo-4-methoxyaniline
Synonyms: N-(2-Bromo-4-methoxyphenyl)acetamide

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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-Acetyl 2-bromo-4-methoxyaniline
CAS number: 79069-37-7

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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: C9H10BrNO2
Molecular weight: 244.1

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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 bromide.

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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-乙酰基-2-溴-4-甲氧基苯胺 在 palladium diacetate 、 copper(l) chloride 、 palladium dichloride 氧气 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 120.0 ℃ 、3.04 MPa 条件下， 反应 24.0h， 生成 1-乙酰基-5-甲氧基吲哚
  参考文献：
  名称：

  Kasahara, Akira; Izumi, Taeko; Murakami, Satoshi, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1405 - 1413

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 N-溴代丁二酰亚胺(NBS) 、 cobalt acetylacetonate 、 三氟乙酸 、 silver(l) oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以80%的产率得到N-乙酰基-2-溴-4-甲氧基苯胺
  参考文献：
  名称：

  钴（ii）催化的苯甲酸酯的区域选择性C–H卤化†

  摘要：

  本文报道了钴催化的区域选择性CH卤化方法。这项工作的重点是对苯甲酸酯的高选择性C–H官能化，这将产生高产率，多功能且实用的卤化产物。由此，以高度选择性的方式实现了许多富电子和电子贫乏的酸酐的溴化，氯化和碘化。还描述了有关反应途径的机理研究。

  DOI：

  10.1039/c8ob01448e

文献信息

• Nickel(II)- and Silver(I)-Catalyzed C–H Bond Halogenation of Anilides and Carbamates
  作者：Ebrahim Kianmehr、Hadi Afaridoun

  DOI：10.1055/s-0040-1705972

  日期：2021.4

  ortho-C–H bond halogenation of anilides and N-aryl carbamates using easily available N-halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.

  已开发了在镍或银催化剂存在下使用易获得的N-卤代琥珀酰亚胺（NXS）作为活性卤化试剂对苯甲酸酯和N-芳基氨基甲酸酯进行邻-C–H键卤化的方法。该方法提供了2-卤代苯胺和氨基甲酸酯的新方法，其可用作合成药物和生物活性化合物的起始材料。
• A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant
  作者：Daichi Kajiyama、Keisuke Inoue、Yuichi Ishikawa、Shigeru Nishiyama

  DOI：10.1016/j.tet.2010.11.015

  日期：2010.12

  Carbazoles were successfully synthesized by oxidative cyclization of the corresponding diaryl derivatives using electrochemically generated hypervalent iodine oxidant. Electron-withdrawing nitro and donating methoxy groups at the para position of the acetamide group interfered with cyclization. Glycozoline (8) was successfully synthesized in five steps with 50% overall yield.

  通过使用电化学生成的高价碘氧化剂对相应的二芳基衍生物进行氧化环化，成功合成了咔唑。乙酰胺基对位的吸电子硝基和给体甲氧基会干扰环化反应。乙二唑啉（8）分五步成功合成，总收率为50％。
• Monoprotected <scp>l</scp> -Amino Acid (<scp>l</scp> -MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp² )−H Bonds by Iridium(III) Catalysis
  作者：Subban Kathiravan、Ian A. Nicholls

  DOI：10.1002/chem.201700280

  日期：2017.5.23

  Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected L-amino acid (L-MPAA) accelerated iridium(III) catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/L-MPAA catalyzed general halogenation

  卤代芳烃是生物活性分子中常见的重要结构基序，可用于有机合成中的多种转化。在本文中，我们报道了在室温下单保护的L-氨基酸（L-MPAA）加速铱（III）催化卤化（杂）苯胺。该反应构成了铱（III）/ L-MPAA通过C（sp2）-H活化催化（杂）芳烃的一般卤化反应的第一个实例。此外，我们证明了该方法在合成喹诺酮衍生物中的应用潜力。
• Rhodium‐Catalyzed <i>ortho</i> ‐Bromination of O‐Phenyl Carbamates Accelerated by a Secondary Amide‐Pendant Cyclopentadienyl Ligand
  作者：Jin Tanaka、Yu Shibata、Anton Joseph、Juntaro Nogami、Jyunichi Terasawa、Ryo Yoshimura、Ken Tanaka

  DOI：10.1002/chem.202000253

  日期：2020.5.7

  RhIII ] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.

  已经确定，新开发的环戊二烯基铑（III）[CpA RhIII]配合物在Cp环上带有酸性仲酰胺部分，能够与N-溴代琥珀酰亚胺（NBS）催化邻氨基苯甲酸酯的邻溴化反应。在室温下。CpA配体上酸性仲酰胺部分的存在通过CpA配体的酸性NH基团和NBS的羰基之间的氢键加速了溴化反应。
• Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)
  作者：Huan Liu、Xuemin Wang、Yonghong Gu

  DOI：10.1039/c0ob00749h

  日期：——

  Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields.

  用1.5当量的苯碘双(trifluoroacetate)（PIFA）和1.0当量的BF3·OEt2在醋酸中室温处理各种酰胺，得到了相应的对位乙氧基化产物，且具有高区位选择性。此外，该反应可以扩展到酰胺的醚化反应。在使用2.0当量的PIFA和2.0当量的BF3·OEt2的条件下，酰胺与醇的反应提供了良产率的相应对位醚化产物。