N-(4-氯苯基)-2-溴苯甲酰胺 | 66569-06-0

• 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-(4-氯苯基)-2-溴苯甲酰胺
• 中文别名: N-(4-氯苯基)2-溴苯甲酰胺；2-溴-n-(4-氯苯基)苯甲酰胺
• 英文名称: 2-bromo-N-(4-chlorophenyl)benzamide
• CAS: 66569-06-0
• 化学式: C₁₃H₉BrClNO
• mdl: MFCD00442557
• 分子量: 310.578
• InChiKey: YFKJGHJQOYPLEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

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-(4-Chlorophenyl) 2-bromobenzamide
Synonyms: 2-Bromo-N-(4-chlorophenyl)benzamide

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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-(4-Chlorophenyl) 2-bromobenzamide
CAS number: 66569-06-0

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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: C13H9BrClNO
Molecular weight: 310.6

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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 chloride, 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-(4-氯苯基)-2-溴苯甲酰胺 在 二-μ-氯双[5-羟基-2-[1-(肟基)乙基]苯基]钯(II)二聚体 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 2-chloro-5-methylphenanthridin-6(5H)-one
  参考文献：
  名称：

  肟衍生钯环催化下的直接芳基化：寻找无磷烷方法

  摘要：

  开发了一种以肟衍生的钯环 1 为催化剂直接芳基化苯并噻唑的无磷烷方法。通过使用芳基溴化物和碘化物，新的催化剂体系可用于 2-芳基化。此外，该方法特别适用于溴和碘酰胺以及氯酰胺的分子内直接偶联，以实现苯并[c]菲啶生物碱的快速合成。

  DOI：

  10.1002/ejoc.201101400
• 作为产物：
  描述：

  2-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-(4-氯苯基)-2-溴苯甲酰胺
  参考文献：
  名称：

  基于 Na2Te 的发散化学计量的无碱铜辅助合成 C2 对称螺环碲烷和联芳基化合物

  摘要：

  已经开发了一种一锅法 Cu( I ) 辅助合成方法，用于通过使用碲双阴离子从 2-溴-N-芳基苯甲酰胺、苯甲醇和苯甲酸制备具有生物学重要意义的C 2 -对称螺二氮杂、苯甲氧基和苯甲氧基碲烷。 (Te 2- ) 在无碱条件下。此外，在相同的反应条件下，通过使用过量的 Na 2 Te 制备了 C-C 偶联联芳基 1,1'-二酰胺。合成的螺二氮杂碲烷可作为还原 H 2 O 2和硝基-迈克尔反应的有效催化剂。

  DOI：

  10.1039/d2cc02181a

文献信息

• A Cu-catalysed synthesis of substituted 3-methyleneisoindolin-1-one
  作者：Anupal Gogoi、Srimanta Guin、Saroj K. Rout、Ganesh Majji、Bhisma K. Patel

  DOI：10.1039/c4ra12782j

  日期：——

  A Cu-catalysed synthesis of substituted isoindolin-1-one has been achieved via a decarboxylative alkynylation–heteroannulation path.

  通过脱羧炔基化-杂环化途径，已经实现了一种取代异吲哚啉-1-酮的Cu催化合成。
• Synthesis and antibacterial activity of 5-methylphenanthridium derivatives as FtsZ inhibitors
  作者：Fang Liu、Henrietta Venter、Fangchao Bi、Susan J. Semple、Jingru Liu、Chaobin Jin、Shutao Ma

  DOI：10.1016/j.bmcl.2017.06.005

  日期：2017.8

  5-Methylphenanthridium derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity and cell division inhibitory activity against various Gram-positive and -negative bacteria. Among them, compounds 5A2, 5B1, 5B2, 5B3, 5C1 and 5C2 displayed the best on-target antibacterial activity with an MIC value of 4 µg/mL against B. subtilis ATCC9372 and S. pyogenes PS, showing

  设计，合成和评估了5-甲基菲啶鎓衍生物对各种革兰氏阳性和阴性细菌的体外抗菌活性和细胞分裂抑制活性。其中化合物5A2，5B1，5B2，5B3，5C1和5C2显示在目标的最佳的抗菌活性用4微克/毫升的抗的MIC值枯草芽孢杆菌ATCC9372和化脓性链球菌PS，显示出比Sanguinarine更好的2倍的活性。SARs表明，在2-位具有烷基侧链的5-甲基菲啶鎓衍生物，尤其是直链烷基侧链发挥了更好的针对目标的抗菌活性。
• Organocatalyst in Direct C(_sp²)–H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed <i>Inter</i>-/<i>Intra</i>-molecular C–H Bond Activation
  作者：Lalit Yadav、Mohit K. Tiwari、Bharti Rajesh Kumar Shyamlal、Sandeep Chaudhary

  DOI：10.1021/acs.joc.0c01019

  日期：2020.6.19

  promotes both inter- and intra-molecular direct C(sp2)–H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C–H arylation of unactivated benzenes with aryl halides (Ar–X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol % organocatalyst, the intra-molecular C–H arylation catalytic system composed of 40 mol % each

  本文介绍的1-（2-羟乙基） -哌嗪的标识为一个新的，高性价比的，高效率的有机催化剂，其促进两者间-和内-分子直接C（SP 2）在未活化的芳烃的芳基化-H叔丁醇钾的存在。当未活化的苯与芳基卤化物（Ar–X； X = I，Br，Cl）朝联芳基合成的分子间C–H芳基化在仅有10 mol％有机催化剂存在下顺利进行，而分子内C–H芳基化催化体系，分别由40摩尔％的催化剂和添加剂（4-二甲基氨基吡啶（DMAP））组成。新型催化剂还能够同时在一个锅中同时进行分子间和分子内直接芳基化。机理研究证实了芳基自由基阴离子的参与，并通过单电子转移（SET）机制进行。较大的底物范围，较高的官能团耐受性，竞争实验，克级合成和动力学研究进一步凸显了该方法的重要性和通用性以及新催化剂的相容性。据我们所知，这是关于任何有机催化剂的第一份报告，该报告以单一形式详细报告了未活化芳烃的分子间和分子内直接C（sp 2）-H芳基化反应。
• Electrochemical Synthesis of 5-Aryl-phenanthridin-6-one by Dehydrogenative N,C Bond Formation
  作者：Anton Kehl、Valentina M. Breising、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1002/chem.201804638

  日期：2018.11.22

  revealed a possible alternative to the catalytic approach. A constant current protocol, undivided cells, and a remarkably low supporting electrolyte concentration enable a novel access to N‐aryl‐phenanthridin‐6‐ones by anodic N,C bond formation using directly generated amidyl radicals. Easy accessible starting materials, a broad scope of applicable functional groups, good yields, and a very simple set‐up are

  目前，5-芳基-菲咯啉-6-酮的一般合成依赖于金属催化的参与。尽管对绿色替代品的需求迫切，但要避免使用需要过渡金属起关键作用的合成路线仍然具有挑战性。在分裂的细胞中采用恒电位方案进行的电化学努力揭示了催化方法的一种可能替代方法。恒定电流方案，未分裂的电池以及非常低的辅助电解质浓度，使得可以使用直接生成的a基通过阳极N，C键形成一种新颖的N-芳基-菲咯啉-6-基团。这种可持续方法的优点是易于获得的起始原料，适用的官能团范围广，产率高以及设置非常简单。
• Palladium-Catalyzed CC Coupling of Aryl Halides with Isocyanides: An Alternative Method for the Stereoselective Synthesis of (3E)-(Imino)isoindolin-1-ones and (3E)-(Imino)thiaisoindoline 1,1-Dioxides
  作者：Bifu Liu、Yibiao Li、Huanfeng Jiang、Meizhou Yin、Huawen Huang

  DOI：10.1002/adsc.201200212

  日期：2012.8.13

  transformation successfully extends its application for the synthesis of phenanthridines and dibenzooxazepines. This new synthetic protocol not only extends the application platform for palladium-catalyzed CC coupling of aryl halides with isocyanides, but also opens atom-economic and step-economic synthetic routes for nitrogen-containing heterocyclic compounds with wide functional group compatibility.

  钯催化的一锅环化反应，通过引入邻位结构来构建（3 E）-（亚氨基）异吲哚啉-1-酮和（3 E）-（亚氨基）硫代异吲哚啉1,1-二氧化物报道了芳基卤上的-反应性官能团。在最佳条件下，环化反应可提供具有良好立体选择性的高至优收率（最高93％）的相应产物。值得注意的是，这种转化成功地扩展了其在菲啶和二苯并恶氮ze合成中的应用。这一新的合成方案不仅扩展了芳基卤化物与异氰化物的钯催化CC偶联的应用平台，而且为具有广泛官能团相容性的含氮杂环化合物开辟了原子经济和分步经济的合成途径。