N-丁基-4-溴苯甲酰胺 | 78080-34-9

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 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-丁基-4-溴苯甲酰胺
• 中文别名: 4-溴-n-丁基苯甲酰胺；4-溴-N-N-丁基苯甲酰胺；4-溴-N-丁基苯甲酰胺
• 英文名称: 4-bromo-N-butylbenzamide
• 英文别名: N-butyl-4-bromobenzamide
• CAS: 78080-34-9
• 化学式: C₁₁H₁₄BrNO
• mdl: MFCD00456169
• 分子量: 256.142
• InChiKey: QSUXNVNNPIUCAH-UHFFFAOYSA-N

物化性质

• 熔点：
  88.5-89 °C
• 沸点：
  364.2±25.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Butyl 4-Bromobenzamide
Synonyms: 4-Bromo-N-butylbenzamide

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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-Butyl 4-Bromobenzamide
CAS number: 78080-34-9

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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: C11H14BrNO
Molecular weight: 256.1

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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-丁基-4-溴苯甲酰胺 在 4-二甲氨基吡啶 、 potassium phosphate 、 偶氮二异丁腈 、 二叔丁基过氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-bromo-2-butyl-4-methyl-4-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)isoquinoline-1,3(2H,4H)-dione
  参考文献：
  名称：

  自由基介导的苯甲酰胺向全氟化或氰化异喹啉二酮的发散环化†

  摘要：

  开发了一种简单高效的苯甲酰胺铜控制的发散环化反应，该反应可导致全氟或氰化异喹啉二酮。在AIBN存在下，甲基丙烯酰基苯甲酰胺与全氟烷基碘进行级联自由基加成/环化反应，在无金属条件下提供全氟代异喹啉二酮为主要产物，而使用CuI（10 mol％）能够使环化重新定向以生成异喹啉二酮。带有一个α-氰基季碳中心。环化具有可控的发散合成和广泛的底物范围以及高度实用的反应条件，从而使该策略成为氟化或氰酸化异喹啉二酮的极具吸引力的手段。

  DOI：

  10.1039/c6ob01550f
• 作为产物：
  描述：

  4-溴苯乙酮 在 硝酸 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 N-丁基-4-溴苯甲酰胺
  参考文献：
  名称：

  乙酰硝酸酯介导甲基酮向多种羧酸衍生物的转化

  摘要：

  描述了一种新型乙酰硝酸盐介导的甲基酮氧化转化为羧酸衍生物的开发。通过类比卤仿反应并得到实验和计算研究的支持，我们提出了这种转变的机制。

  DOI：

  10.1039/d1ob00786f

文献信息

• PROCESS FOR THE REMOVAL AND RETURN OF A CATALYST TO A LIQUID PHASE MEDIUM
  申请人：PHOSPHONICS LTD

  公开号：US20150299229A1

  公开（公告）日：2015-10-22

  A process for the selective removal of a component from a liquid phase and subsequently returning the component to a liquid phase is disclosed. A novel compound of formula (I) [SUP]-[[L]-[G]]a (I) in which L is a linking group, G is an aryl group having a leaving group LG selected from Cl, Br, I, sulfonate such as triflate, a diazo group, a nitrile, an ester and an alkoxy group and substituent Q is selected from H, NR2, OR, C02R, F, Cl, N02 CN and SUP is a support having a plurality of groups -[L]-[G] bound to the support is contacted with the liquid phase to bind the component to the compound I thereby forming a captured component which is separated from and may be returned to the liquid phase. The compound I is especially useful in binding homogeneous catalysts to remove it from a reaction medium and selectively returning the catalyst to the reaction medium at a later stage. The compound is particularly useful for cross-coupling reactions, for example in Suzuki reactions.

  揭示了一种从液相中选择性去除组分并随后将该组分返回到液相的方法。公开了一种具有式(I)的新化合物[SUP]-[[L]-[G]]a (I)，其中L是连接基团，G是一种芳基团，具有从Cl、Br、I、磺酸盐（如三氟甲磺酸盐）、重氮基团、腈基、酯基和烷氧基中选择的离去基团LG，取代基Q从H、NR2、OR、C02R、F、Cl、N02、CN中选择，SUP是具有多个与支持物相结合的基团-[L]-[G]的支持物，与液相接触以将组分结合到化合物I中，从而形成被捕获的组分，该组分与液相分离并可以返回到液相中。化合物I在将均相催化剂结合以将其从反应介质中去除，并在后续阶段选择性地将催化剂返回到反应介质中方面特别有用。该化合物特别适用于交叉偶联反应，例如在铃木反应中。
• NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds
  作者：Yuqi Zhang、Xiaojing Ye、Sicheng Liu、Wei Chen、Irfan Majeed、Tingting Liu、Yulin Zhu、Zhuo Zeng

  DOI：10.1039/d1ob01409a

  日期：——

  Multifunctional transformation of amide C–N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution

  报道了酰胺C-N键断裂的多功能转化。该协议适用于在 NaOT 催化的类似反应条件下的苯甲酰胺、硫代酰胺、醇和硫醇。值得注意的是，NaOTs 不仅可以回收和重复使用多达三个循环而不会显着降低催化活性，而且还可以催化克级反应。本研究为多种酰胺的转化提供了一种条件温和、程序简单的新型解决方案。
• A CO₂-Catalyzed Transamidation Reaction
  作者：Yang Yang、Jian Liu、Fadhil S. Kamounah、Gianluca Ciancaleoni、Ji-Woong Lee

  DOI：10.1021/acs.joc.1c02077

  日期：2021.12.3

  Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2 as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid

  在过量化学计量的活化试剂和/或过渡金属催化剂的存在下，转酰胺基反应通常由反应性底物介导。在这里，我们报告了使用 CO 2作为无痕催化剂：在催化量的 CO 2存在下，使用伯、仲和叔酰胺供体加速转酰胺反应。包括氨基酸衍生物在内的各种胺类亲核试剂都被耐受，这表明转酰胺基在肽修饰和聚合物降解中的实用性（例如，Nylon-6,6）。特别是，N , O -二甲基羟基酰胺（Weinreb 酰胺）在 CO 2催化的转酰胺基反应中与 N 2相比表现出明显的反应性大气层。进行了比较 Hammett 研究和动力学分析，以阐明分子 CO 2的催化活化机制，这得到了 DFT 计算的支持。我们将CO 2在转酰胺基反应中的积极作用归因于通过与亲电子CO 2共价结合来稳定四面体中间体。
• CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in water <i>via</i> benzylic sp³ C–H activation
  作者：Marzieh Rousta、Dariush Khalili、Ali Khalafi-Nezhad、Edris Ebrahimi

  DOI：10.1039/d1nj03982b

  日期：——

  activity of the rGO/Fe3O4–CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals using tert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation

  通过简便的化学方法制备了磁铁矿还原的氧化石墨烯负载的 CuO 纳米复合材料 ( rGO /Fe 3 O 4 –CuO)，并通过傅里叶变换红外光谱 (FTIR)、X 射线衍射 (XRD)、UV-vis光谱、扫描电子显微镜 (SEM)、透射电子显微镜 (TEM)、能量色散光谱 (EDS)、Brunauer-Emmett-Teller (BET) 分析、振动样品磁强计 (VSM) 和热重 (TG) 分析。rGO/Fe 3 O 4的催化活性-CuO纳米复合材料在甲基芳烃与游离胺的直接氧化酰胺化反应中被探测到。使用叔丁基过氧化氢 (TBHP) 作为“绿色”氧化剂和在水中的低毒性 TBAI，在室温下从廉价的原料化学品中有效地制备了各种芳香族和脂肪族酰胺。该方法将甲基芳烃的氧化和酰胺键的形成结合到一个操作中。此外，合成的纳米复合材料可以使用外部磁铁从反应混合物中分离出来，并在连续六次运行中重复使用，催化活性没有明显降低。
• Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
  作者：Céline Guissart、Andre Barros、Luis Rosa Barata、Gwilherm Evano

  DOI：10.1021/acs.orglett.8b01896

  日期：2018.9.7

  An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted

  报道了一种在温和条件下将酰亚胺转化为一系列羧酸衍生物的有效，广泛适用，操作简单和发散的方法。通过简单地使用催化量的镱（III），三氟甲磺酸，如醇的存在下，路易斯酸的启动子，水，胺，或Ñ，Ô -dimethylhydroxylamine，宽范围的酰亚胺是平滑且容易地转化为相应的酯，羧酸，酰胺和Weinreb酰胺的收率很高。该方法尤其使得容易裂解基于恶唑烷酮的助剂。