N-丙基-2-溴苯甲酰胺 | 346695-08-7

• 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-丙基-2-溴苯甲酰胺
• 中文别名: 2-溴-n-丙基苯甲酰胺
• 英文名称: 2-bromo-N-propylbenzamide
• CAS: 346695-08-7
• 化学式: C₁₀H₁₂BrNO
• mdl: MFCD01212206
• 分子量: 242.115
• InChiKey: XNIZYPMLUVRLJS-UHFFFAOYSA-N

物化性质

• 沸点：
  342.9±25.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)
• 保留指数：
  1808

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-Propyl 2-bromobenzamide
Synonyms: 2-Bromo-N-propylbenzamide

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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-Propyl 2-bromobenzamide
CAS number: 346695-08-7

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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: C10H12BrNO
Molecular weight: 242.1

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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-丙基-2-溴苯甲酰胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 methyl 2-{[3-bromo-2-(propylcarbamoyl)phenyl]methyl}-3,3,3-trifluoropropanoate
  参考文献：
  名称：

  铑（III）通过定向CH键裂解催化α-三氟甲基丙烯酸与苯甲酰胺的氧化还原-中性偶联。

  摘要：

  铑（III）催化的α-三氟甲基丙烯酸与苯甲酰胺的氧化还原-中性偶合顺利进行，同时酰胺定向的CH键断裂，生成β-[2-（氨基羰基）苯基]-α-三氟甲基丙酸衍生物。产物之一可以转化为三氟甲基取代的杂环化合物。另外，α-三氟甲基丙烯酸与具有含氮定向基团的相关芳族底物的氧化还原-中性偶联也可以在类似条件下进行。

  DOI：

  10.1002/asia.201901776
• 作为产物：
  描述：

  N-丙基苯甲酰胺 在 sodium persulfate 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以63%的产率得到N-丙基-2-溴苯甲酰胺
  参考文献：
  名称：

  区域和化学选择性C ？弱配位的H氯化/缺电子芳烃的溴化和相对方向基团能力的研究

  摘要：

  都是相对的：已经开发了一种实用而有效的Pd II催化的区域和化学选择性氯化/溴化反应，可轻松合成各种芳族氯化物。该反应显示出优异的反应活性，良好的官能团耐受性和高收率。进行了一项初步研究，以评估各种功能的相对指导能力。

  DOI：

  10.1002/anie.201300176

文献信息

• Synthesis of 1-Aminoisoquinolines by Gold(III)-Mediated Domino Reactions from 2-Alkynylbenzamides and Ammonium Acetate
  作者：Yuhua Long、Zhigang She、Xiaochen Liu、Yu Chen

  DOI：10.1021/jo302794z

  日期：2013.3.15

  1-aminoisoquinoline derivatives by gold(III)-mediated domino reactions is described. This synthetic protocol starts from readily available 2-alkynylbenzamides and ammonium acetate and takes place under mild reaction conditions compatible with a variety of functional groups. A plausible mechanism for the domino process is proposed, supported by the reaction of a possible intermediate, N-(3-phenyl-1H-isochrom

  描述了一种通过金（III）介导的多米诺反应向药学上感兴趣的1-氨基异喹啉衍生物的简便合成路线。该合成方案从容易获得的2-炔基苯甲酰胺和乙酸铵开始，并且在与各种官能团相容的温和反应条件下进行。提出了一种可行的多米诺骨牌机制，并由一种可能的中间体N-（3-苯基-1H-异色烯-1-亚烷基）丙-1-胺的反应所支持。
• 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。
• Ligand-Controlled Chemoselective One-Pot Synthesis of Dibenzothiazepinones and Dibenzoxazepinones via Twice Copper-Catalyzed Cross-Coupling
  作者：Yanyu Chen、Qiujun Peng、Rong Zhang、Jian Hu、Yijun Zhou、Lanting Xu、Xianhua Pan

  DOI：10.1055/s-0036-1558959

  日期：2017.6

  from 2-bromobenzamides and 2-bromo(thio)phenols via twice copper-catalyzed couplings to afford dibenzothiazepines and dibenzoxazepinones has been developed. High levels of yield and chemoselectivity are achieved in a single-pot reaction by using an appropriate ligand. Moreover, this facile methodology allows rapid access to a variety of bio­active compounds and known psychotropic drug, which should

  已经开发了一种高效且普遍适用的协议，从 2-溴苯甲酰胺和 2-溴（硫）酚开始，通过两次铜催化偶联，提供二苯并噻嗪类和二苯并恶唑酮。通过使用合适的配体，在单锅反应中实现了高水平的产量和化学选择性。此外，这种简便的方法可以快速获得各种生物活性化合物和已知的精神药物，这将扩大其在有机合成中的应用。
• 光诱导无金属催化的碳芳基化串联反应合成 杂环化合物的方法
  申请人：河南大学

  公开号：CN108947900B

  公开（公告）日：2021-07-30

  本发明属于有机合成技术领域，公开了一种光诱导无金属催化的碳芳基化串联反应合成杂环化合物的方法，包括以下步骤：以式III所示的化合物与式IV所示的化合物为底物，在有机溶剂中，在光敏剂和碱性化合物作用下，在室温光照条件下，搅拌24‑48小时，淬灭反应，萃取，洗涤，干燥，浓缩，纯化得到式I或式II所示的杂环化合物。本发明在室温光照下反应，无金属催化，与传统Ullmann‑Hurtley偶联关环反应相比，无需添加催化剂，只需在室温条件下反应，能量消耗低，同时也大大减少了副反应的发生，绿色环保。
• An efficient synthesis of biaryl diamides via Ullmann coupling reaction catalyzed by CuI in the presence of Cs2CO3 and TBAB
  作者：Fang Dong、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1007/s11164-018-3422-0

  日期：2018.9

  Abstract CuI accompanyied by Cs2CO3 and TBAB was confirmed to be an efficient catalyst combination to promote an Ullmann coupling reaction. It facilitated 2-bromobenzamides to undergo a coupling reaction for the synthesis of symmetrical biaryldiamides in moderate yields at 120 °C under Pd-free conditions. Graphical Abstract

  摘要 Cs 2 CO 3和TBAB伴随的CuI被证实是促进Ullmann偶联反应的有效催化剂组合。它促进了2-溴苯甲酰胺在无钯条件下于120°C进行偶联反应，以中等收率合成对称的联芳基二酰胺。 图形概要