N-(2-甲基苯基)-2-溴苯甲酰胺 | 303991-47-1

• 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-(2-甲基苯基)-2-溴苯甲酰胺
• 中文别名: N-(2-甲基苯基)2-溴苯甲酰胺
• 英文名称: 2-bromo-N-(o-tolyl)benzamide
• 英文别名: 2-bromo-N-(2-methylphenyl)benzamide
• CAS: 303991-47-1
• 化学式: C₁₄H₁₂BrNO
• mdl: MFCD00783656
• 分子量: 290.159
• InChiKey: OFBSLVLRQPIIMG-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  317.8±35.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-(2-Methylphenyl) 2-bromobenzamide
Synonyms: 2-Bromo-N-o-tolylbenzamide

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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-(2-Methylphenyl) 2-bromobenzamide
CAS number: 303991-47-1

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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: C14H12BrNO
Molecular weight: 290.2

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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, 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-(2-甲基苯基)-2-溴苯甲酰胺 在 copper(l) iodide 、 caesium carbonate 、 六甲基二硅氮烷 、 zinc(II) chloride 、 L-羟基脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 海米那
  参考文献：
  名称：

  Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation

  摘要：

  Cul/4-hydroxy-L-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 degrees C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.

  DOI：

  10.1021/ol300084v
• 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-(2-甲基苯基)-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

• 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。
• Direct Arylation under Catalysis of an Oxime-Derived Palladacycle: Search for a Phosphane-Free Method
  作者：Guofu Zhang、Xiaobao Zhao、Yunbing Yan、Chengrong Ding

  DOI：10.1002/ejoc.201101400

  日期：2012.2

  for the direct arylation of benzothiazole by employing oxime-derived palladacycle 1 as a catalyst was developed. The new catalyst system can be used for 2-arylations by using aryl bromides and iodides. In addition, this method is especially suitable for the intramolecular direct coupling of bromo- and iodoamides, as well aschloroamides, to achieve a rapid synthesis of benzo[c]phenanthridine alkaloids

  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。
• Practical Synthesis of Phenanthrid­inones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to<i>o</i>-Chlorobenzamides
  作者：Hailong Liu、Weibiao Han、Chun Li、Zhiyong Ma、Ruixiang Li、Xueli Zheng、Haiyan Fu、Hua Chen

  DOI：10.1002/ejoc.201501170

  日期：2016.1

  domino reaction proceeds through a sequential C–C and C–N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover

  通过在 N,N-二甲基乙酰胺中使用不含膦的钯催化剂，开发了一种从邻卤苯甲酰胺中高效构建菲啶酮衍生物的方法。多米诺反应在一个锅中通过连续的 C-C 和 C-N 键形成过程进行。该协议展示了广泛的底物范围，并以高达 93% 的产率提供了一系列菲啶酮。重要的是，该协议也可应用于反应性较低的邻氯苯甲酰胺。该方法构成了从这种底物合成菲啶酮的第一个例子。此外，克级反应的成功表明，这个操作简单的过程是可扩展的。
• Reductive Hydrodehalogenation of Halogenated Carboxylic Acid Derivatives Using a DMSO/HCOONa·2H₂O System
  作者：Guyue Liu、Feiyue Hao、Lingling Liang、Zhengneng Jin、Jiashou Wu

  DOI：10.1021/acs.orglett.3c00782

  日期：2023.4.21

  A practical and operationally simple hydrodehalogenation of halogenated carboxylic acid derivatives using a DMSO/HCOONa·2H2O system is developed. This protocol avoids the involvement of light irradiation, electrochemical apparatus, transition metals, radical initiators, strong bases, and other additional additives. Control experiments suggest that HCOONa might function as a hydride donor in the reduction

  开发了使用 DMSO/HCOONa·2H 2 O 系统对卤代羧酸衍生物进行实用且操作简单的加氢脱卤。该协议避免了光照射、电化学装置、过渡金属、自由基引发剂、强碱和其他附加添加剂的参与。对照实验表明，HCOONa 可能在通过亲核取代或加成实现加氢脱卤的还原过程中充当氢化物供体。
• Copper-catalyzed direct synthesis of 3-methylene-2-arylisoindolin-1-ones with calcium carbide as a surrogate of gaseous acetylene
  作者：Jianglong Wu、Yinfeng Ma、Yan Wang、Chenyu Wang、Hui Luo、Dianjun Li、Jinhui Yang

  DOI：10.1039/d2gc03572c

  日期：——

  A novel strategy for the synthesis of 3-methylene-2-arylisoindolin-1-ones through Sonogashira cross-coupling/nucleophilic addition reactions using calcium carbide as a surrogate of gaseous acetylene, 2-bromo-N-(2-bromophenyl)benzamide substrates as starting materials, and copper as a catalyst was described. The salient features of this protocol are the use of a readily available and easy-to-handle

  一种通过 Sonogashira 交叉偶联/亲核加成反应合成 3-methylene-2-arylisoindolin-1-ones 的新策略，使用碳化钙作为气态乙炔、2-溴-N-(2-溴苯基)苯甲酰胺底物的替代物作为起始材料，铜作为催化剂进行了描述。该协议的显着特点是使用现成且易于处理的炔烃源、广泛的基板范围、露天条件、水系统和简单的操作程序。此外，这种方法可以扩大到克规模。