4-溴-苯甲酰苯胺 | 6846-12-4

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: 4-溴-苯甲酰苯胺
• 中文别名: N-苯基-4-溴苯甲酰胺；4-溴苯甲酰苯胺
• 英文名称: 4-bromo-N-phenyl-benzamide
• 英文别名: N-phenyl-4-bromobenzamide；4-bromobenzanilide；4-Brom-benzanilid；4-bromo-N-phenylbenzamide
• CAS: 6846-12-4
• 化学式: C₁₃H₁₀BrNO
• mdl: MFCD00624477
• 分子量: 276.132
• InChiKey: QVTGXXQAVWWJRO-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  304.7±25.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 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

• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N-Phenyl 4-bromobenzamide
Product Name:
Synonyms: 4-Bromo-N-phenylbenzamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
N-Phenyl 4-bromobenzamide
Ingredient name:
CAS number: 6846-12-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H10BrNO
Molecular weight: 276.1

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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：

  4-溴-苯甲酰苯胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 4-(吗啉-4-羰基)溴苯
  参考文献：
  名称：

  N-C裂解制备仲酰胺的无金属氨基转移

  摘要：

  酰胺基转移反应代表了一个基本的化学过程，涉及一个酰胺官能团向另一个酰胺官能团的转化。在这里，我们报告一个浅显的，高度化学选择性方法的转- ñ -叔-丁氧基羰基化（N-Boc）活化的仲酰胺，在没有任何添加剂的情况下，在极其温和的条件下进行。由于该反应是在不存在金属，氧化剂或还原剂的情况下进行的，因此该反应具有许多有用的功能。该反应与各种酰胺和亲核胺相容，通过直接亲核加成至酰胺键，以优异的收率提供了转酰胺基化产物。直接从酰胺键合成市售止吐药Tigan时，强调了该方法的实用性。我们预期，这种新的无金属的氨基转移将对涉及将直接亲核加成酰胺键作为关键步骤的新转化的发展产生广泛的影响。

  DOI：

  10.1021/acs.joc.9b02013
• 作为产物：
  描述：

  4-溴苯甲酰苯 在 硫酸 、 一水合肼 、 sodium nitrite 作用下， 反应 2.0h， 生成 4-溴-苯甲酰苯胺
  参考文献：
  名称：

  The Rearrangement of Hydrazones and Semicarbazones

  摘要：

  DOI：

  10.1021/ja01119a037

文献信息

• Efficient cobalt-catalyzed C–N cross-coupling reaction between benzamide and aryl iodide in water
  作者：Bryan Yong-Hao Tan、Yong-Chua Teo

  DOI：10.1039/c4ob01483a

  日期：——

  A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)·2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.

  报道了一种在水中Co（C 2 O 4）·2H 2 O / dmeda体系催化苯甲酰胺N-芳基化反应的实用有效策略。在优化的条件下，使用取代的芳基碘化物可以以高收率（高达92％）获得各种各样的N-芳基化产物。
• Platinum nanowires catalyzed direct amidation with aldehydes and amines
  作者：Dawei Xu、Linyan Shi、Danhua Ge、Xueqin Cao、Hongwei Gu

  DOI：10.1007/s11426-015-5552-1

  日期：2016.4

  Different from the conventional synthesis methods and substrates, we designed a brand new method for synthesizing amides with platinum nanowires as catalysts and tert-butylhydroperoxide (TBHP) as the oxidant. Influence of factors, such as the catalyst, solvents, and the reaction temperature, were studied to determine the optimal reaction conditions. In addition, we explored the substrate generality

  与常规合成方法和底物不同，我们设计了一种全新的方法，以铂纳米线为催化剂，叔丁基过氧化氢（TBHP）为氧化剂合成酰胺。研究了催化剂，溶剂和反应温度等因素的影响，确定了最佳反应条件。此外，我们探索了基材的通用性并观察到了优异的产量。
• 一种铂纳米线催化合成酰胺类化合物的方法
  申请人：苏州大学

  公开号：CN104086345B

  公开（公告）日：2016-06-08

  本发明涉及一种铂纳米线催化合成酰胺类化合物的方法。具体而言，该方法包括如下步骤：向反应容器中加入分散于醇中的铂纳米线，减压除去醇，进一步加入三氯化铝、反应溶剂、吡啶、胺类化合物、醛类化合物和氧化剂，在搅拌的条件下，于油浴中加热反应，之后通过柱层析进行纯化，得到酰胺类化合物，其中：所述醛类化合物、胺类化合物、三氯化铝、吡啶、铂纳米线和氧化剂的摩尔比为0.5~3:0.5~3:0.1~0.5:0.5~2:0.1%~2%:0.5~5，所述加热反应的反应温度为80~140℃，反应时间为16~24小时。由于采用铂纳米线作为催化剂，本发明不仅催化活性高，而且性能稳定，同时本发明的方法能得到较高的产率，条件温和，工艺简单，易于操作。
• Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates
  作者：Amit Banerjee、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1055/a-1504-8366

  日期：2023.1

  Bimolecular nucleophilic substitution (SN2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic

  双分子亲核取代 (SN2) 是有机化学中最著名的基本反应之一，用于从两个分子生成新分子。原则上，亲核试剂从具有合适离去基团（最常见的是卤化物）的烷化剂的背面攻击。然而，烷基卤价格昂贵、非常有害、有毒且不稳定，这使得它们在实验室使用中存在问题。相比之下，磷酸三烷基酯价格低廉、易于获得且在室温、空气中稳定且易于处理，但很少用作有机合成中的烷基化剂。在这里，我们描述了一种使用现成的磷酸三烷基酯对各种 N-、O-、C- 和 S-亲核试剂进行亲核烷基化的温和、直接和强大的方法。反应以优异的收率顺利进行，和定量产量在许多情况下，并涵盖广泛的底物。此外，通过手性中心构型的反转（高达 98% ee）实现了仲烷基的罕见立体选择性转移。
• Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
  作者：Huifeng Yue、Chen Zhu、Magnus Rueping

  DOI：10.1002/anie.201711104

  日期：2018.1.26

  catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also

  首次实现了芳基、杂芳基和乙烯基卤化物的高效光氧化还原/镍催化磺酰化反应。这种新开发的磺酰化方案为在室温下合成多种芳族砜提供了一种通用方法，并显示出优异的官能团耐受性。亲电偶联配对物不限于芳基、杂芳基和乙烯基溴化物和碘化物，还包括反应性较低的芳基氯化物作为该转化的合适底物。