N-乙基-2-溴苯甲酰胺 | 80031-02-3

• 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-乙基-2-溴苯甲酰胺
• 中文别名: 2-溴-N-乙基苯甲酰胺
• 英文名称: 2-bromo-N-ethylbenzamide
• 英文别名: N-ethyl-2-bromobenzamide
• CAS: 80031-02-3
• 化学式: C₉H₁₀BrNO
• mdl: MFCD01211894
• 分子量: 228.088
• InChiKey: DWCBZUWYUAIEEP-UHFFFAOYSA-N

物化性质

• 熔点：
  91-95
• 沸点：
  330.5±25.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Ethyl 2-bromobenzamide
Synonyms: 2-Bromo-N-ethylbenzamide

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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-Ethyl 2-bromobenzamide
CAS number: 80031-02-3

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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: C9H10BrNO
Molecular weight: 228.1

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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-乙基-2-溴苯甲酰胺 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 cesium acetate 、 异丙醇 作用下， 以93%的产率得到N-乙苯甲醯胺
  参考文献：
  名称：

  钌（II）配合物催化的有机卤化物的转移加氢脱卤

  摘要：

  报道了一种使用2-丙醇溶剂作为氢化物源的简单有效的Ru（II）催化有机卤化物转移加氢脱卤的方法。该方法适用于多种芳香卤化物以及α-卤代酯和酰胺的加氢脱卤，而无需其他配体，并且在许多情况下均实现了定量收率。该方法的潜在合成应用通过有效的克级转化和低至0.5 mol％的催化剂负载得到证明。

  DOI：

  10.1021/acs.joc.6b02222
• 作为产物：
  描述：

  2-溴苯甲酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 N-乙基-2-溴苯甲酰胺
  参考文献：
  名称：

  酸性氘到卤素-锂交换位点的正式分子内转移是否表明锂-卤素交换比失去酸性氘更快？支持替代机制的证据

  摘要：

  酸性氘正式分子内转移到卤素-锂交换位点的反应可以解释为表明最初的卤素-锂交换发生得比酸性氘的损失更快。然而，对 N-deuterio-N-烷基-o、-m-和-p-卤代苯甲酰亚胺的卤素-金属-氘损失之间的竞争的研究与该机制不一致。他们提出了一种替代方案，其中酸性氘的初始损失随后是卤素-锂交换以得到二锂化的中间体。然后通过二锂化物质与未反应的 N-氘化酰胺发生分子间反应，将氘转移到卤素-锂交换位点。卤素-锂交换比反应物的完全混合更快，并且可以在最初形成的去质子化络合物中或在有机锂试剂的瞬时高局部浓度中发生。提供了两种可能性的证据。已经重新研究了文献中卤素-锂交换似乎比酸性氢的转移更快的两个反应，并发现它们可以用相似的序列来解释。

  DOI：

  10.1021/ja00219a031

文献信息

• Modular Approach to Tricyclic Heterocycles through Copper Catalysis and Functionalization by Palladium-Catalyzed C-H Arylation
  作者：Esa T. T. Kumpulainen、Antonia Högnäsbacka

  DOI：10.1002/ejoc.201700356

  日期：2017.5.10

  Oxidative copper‐catalyzed ring construction gives modular access to tricyclic heteroaryls. These structures are further substituted by palladium‐catalyzed C–H activation together with aryl bromides containing various functional groups.

  氧化铜催化的环结构使获得三环杂芳基的方法变得模块化。这些结构进一步被钯催化的C–H活化以及含有各种官能团的芳基溴化物所取代。
• 一种化工中间体2,2′-二硫代二苯酰胺类化合 物的制备方法
  申请人：上海交通大学

  公开号：CN111269159B

  公开（公告）日：2021-11-02

  本发明提供一种化工中间体2,2'‑二硫代二苯酰胺类化合物的制备方法，2‑位取代的苯甲酰胺类化合物与硫试剂，在金属盐与配体的共同作用下，在高沸点、非质子溶剂中反应，生成2,2'‑二硫代二苯酰胺类化合物；本发明2,2'‑二硫代二苯酰胺类化合物为一种重要的化工中间体，合成工艺路线简单，在降低成本的同时减少三废对环境的污染。
• Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin
  作者：Shenghai Guo、Yan Li、Li Tao、Wenwen Zhang、Xuesen Fan

  DOI：10.1039/c4ra10799c

  日期：——

  procedure for the preparation of 2-substituted and 2,3-disubstituted quinazolinones was achieved through copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia under air. Control experimental results indicated that this tandem reaction is triggered by a copper-catalyzed direct amination of 2-bromobenzamides with aqueous ammonia, followed by cyclocondensation and oxidative

  通过2-溴苯甲酰胺与醛和氨水在空气中的铜催化串联反应，实现了制备2-取代的和2,3-二取代的喹唑啉酮的有效而实用的程序。对照实验结果表明，该串联反应是通过铜催化的2-溴苯甲酰胺与氨水的直接胺化反应，然后进行环缩合和氧化芳构化而引发的。作为一种应用，这种新颖的方法为生物碱类胰蛋白酶的合成提供了一种简洁实用的一锅法。
• A copper catalyzed multicomponent cascade redox reaction for the synthesis of quinazolinones
  作者：Mahesh H. Shinde、Umesh A. Kshirsagar

  DOI：10.1039/c6ra10997g

  日期：——

  A copper catalyzed multicomponent cascade redox reaction for the synthesis of various quinazolinones starting from easily available 2-bromobenzamides, benzylic alcohols and sodium azide as a nitrogen source has been developed. The reaction involves copper catalyzed azidation of 2-bromobenzamide via an SNAr reaction and oxidation of benzyl alcohol followed by sequential reduction–condensation–oxidation

  已经开发了一种铜催化的多组分级联氧化还原反应，用于从容易获得的2-溴苯甲酰胺，苯甲醇和叠氮化钠作为氮源开始合成各种喹唑啉酮。该反应涉及通过S N Ar反应进行铜催化的2-溴苯甲酰胺叠氮化和苯甲醇的氧化，然后依次进行还原-缩合-氧化以生成喹唑啉酮。
• Palladium-Catalyzed Annulation of Arynes by <i>o</i>-Halobenzamides: Synthesis of Phenanthridinones
  作者：Chun Lu、Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1021/jo3016192

  日期：2012.10.5

  The palladium-catalyzed annulation of arynes by substituted o-halobenzamides produces N-substituted phenanthridinones in good yields. This methodology provides this important heterocyclic ring system in a single step by simultaneous C–C and C–N bond formation, under relatively mild reaction conditions, and tolerates a variety of functional groups.

  通过取代的邻卤代苯甲酰胺钯催化的芳炔环化以良好的产率产生N-取代的菲啶酮。该方法通过在相对温和的反应条件下同时形成 C-C 和 C-N 键，一步提供了这种重要的杂环系统，并且可以耐受多种官能团。