1-(3-溴-4-甲氧基苯基)乙烯酮 | 35310-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-溴-4-甲氧基苯基)乙烯酮
• 中文别名: 3'-溴-4'-甲氧基苯乙酮；3-溴-4-甲氧基苯乙酮
• 英文名称: 3-bromo-4-methoxyacetophenone
• 英文别名: 1-(3-bromo-4-methoxyphenyl)ethanone；1-(3-bromo-4-methoxyphenyl)ethan-1-one；3'-Brom-4'-methoxyacetophenon
• CAS: 35310-75-9
• 化学式: C₉H₉BrO₂
• mdl: MFCD01812494
• 分子量: 229.073
• InChiKey: JYPGOBDETCKKKV-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86°C
• 密度：
  1.421

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(3-Bromo-4-methoxyphenyl)ethanone
Synonyms:

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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: 1-(3-Bromo-4-methoxyphenyl)ethanone
CAS number: 35310-75-9

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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: C9H9BrO2
Molecular weight: 229.1

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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, 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：

  1-(3-溴-4-甲氧基苯基)乙烯酮 在 乙硫醇钠 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-乙酰基-2-羟基苯甲腈
  参考文献：
  名称：

  3-溴-5-(2-乙基咪唑并[1,2-a]吡啶-3-羰基)-2-羟基苯甲腈的合成

  摘要：

  本发明公开了一种3‑溴‑5‑(2‑乙基咪唑并[1,2‑a]吡啶‑3‑羰基)‑2‑羟基苯甲腈的合成方法，特别是涉及一种式(III)化合物的合成方法，具体涉及步骤A或者步骤B；步骤A：式(I)化合物与式(II)化合物先在有机溶剂中加热进行反应，所得反应产物与碱再在水存在的条件下加热继续反应，得到式(III)化合物；步骤B：式(I)化合物与式(II)化合物和碱先在有机溶剂中加热进行反应，所得反应产物再在水存在的条件下加热继续反应，得到式(III)化合物。

  公开号：

  CN111410654B
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 碘 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以97%的产率得到1-(3-溴-4-甲氧基苯基)乙烯酮
  参考文献：
  名称：

  N-溴代琥珀酰亚胺碘催化芳基醚芳族溴化反应的机理

  摘要：

  尽管近年来碘催化的反应发展迅速，但是碘催化溴化的例子很少，这些反应的机理尚不清楚。在本文中，我们报道了NBS的I 2催化的芳基醚的芳族溴化反应，并详细介绍了包括动力学研究和动力学同位素效应在内的机理研究。研究表明，该反应实际上是由诱导期形成的IBr催化的，而决定速率的步骤是在IBr辅助下消除Wheland中间体的HBr。

  DOI：

  10.1016/j.tet.2017.10.073

文献信息

• Direct Transformation of Ethylarenes into Primary Aromatic Amides with <i>N</i>-Bromosuccinimide and I₂–Aqueous NH₃
  作者：Shohei Shimokawa、Yuhsuke Kawagoe、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1021/acs.orglett.6b00048

  日期：2016.2.19

  α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes.

  通过在乙酸乙酯和水，乙腈和水的混合物中催化量的2,2'-偶氮二（异丁腈）存在下用N-溴琥珀酰亚胺处理，将各种乙基芳烃高收率转化为相应的伯芳族酰胺。，或氯仿和水，然后在一个锅中与分子碘和NH 3水溶液反应。发现在第一反应步骤中形成芳基α-溴甲基酮和/或芳基甲基酮，并且在第二反应步骤中发生它们的碘仿型反应以提供伯芳族酰胺。本反应是用于从乙基芳烃制备伯芳族酰胺的有用且实用的无过渡金属的方法。
• Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides
  作者：Rui-Hua Liu、Qi-Chao Shan、Ya Gao、Teck-Peng Loh、Xu-Hong Hu

  DOI：10.1016/j.cclet.2020.10.007

  日期：2021.4

  efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical

  本文公开了一种有效的Ag催化的酰胺与α-羰基亚砜基鎓盐的[4 + 1]杂环化反应。非对映选择性转化为多种多样的多功能恶唑啉衍生物提供了实用途径。所得的四取代恶唑啉的合成效用通过对药物相关的有价值的组成部分进行的一系列有用操作而得到进一步证明。
• Electrooxidation of Alcohols in an<i>N</i>-Oxyl-Immobilized Poly(ethylene-<i>co</i>-acrylic acid)/Water Disperse System
  作者：Hideo Tanaka、Jun Kubota、Seiji Miyahara、Manabu Kuroboshi

  DOI：10.1246/bcsj.78.1677

  日期：2005.9

  The electrooxidation of alcohols in a disperse system with N-oxyl-immobilized polymer particles (PE-co-AA-N-Oxyl), prepared from poly(ethylene-co-acrylic acid) (PE-co-AA-CO2H), as a disperse phase and an aqueous saturated NaHCO3 containing 20 wt % NaBr as a disperse medium was successfully performed in a simple beaker-type undivided cell under constant-current conditions. The electrooxidation of alcohols proceeded in a similar manner by the use of PE-co-AA-CO2H as a disperse phase, though the current efficiency decreased in some extent. Protection of most of the carboxylic acid moieties on the surface of PE-co-AA-CO2H by esterification or amidation resulted in significant decrease of the product yields, suggesting that the carboxylic acid moieties on the surface of PE-co-AA-CO2H would also act as a mediator for the electrooxidation of alcohols. Both the recovered PE-co-AA-N-Oxyl and the aqueous solution were used repeatedly for the electrooxidation of alcohols, thereby offering a formally closed system for the electrooxidation of alcohols.

  在采用N-氧基固定化聚合物颗粒（PE-co-AA-N-Oxyl）作为分散相，以及含有20 wt% NaBr的饱和NaHCO3水溶液作为分散介质的分散体系中，成功地在一简单的杯型无隔膜电池中在恒电流条件下进行了醇的电氧化。通过使用PE-co-AA-CO2H作为分散相，醇的电氧化过程与此类似，尽管电流效率在某种程度上有所降低。通过酯化或酰胺化保护PE-co-AA-CO2H表面上的大多数羧酸官能团导致产品收率显著降低，表明PE-co-AA-CO2H表面上的羧酸官能团也会作为醇电氧化的介体。回收的PE-co-AA-N-Oxyl和水溶液均可重复用于醇的电氧化，从而为醇的电氧化提供了一个形式上的封闭系统。
• Electrooxidation of Alcohols in <i>N</i>-Oxyl-Immobilized Silica Gel/Water ­Disperse System: Approach to Totally Closed System
  作者：Manabu Kuroboshi、Kentaro Goto、Hideo Tanaka

  DOI：10.1055/s-0028-1087987

  日期：——

  Electrooxidation of alcohols in a disperse system with N-oxyl-immobilized silica gel as a disperse phase and an aqueous NaBr/NaHCO3 solution as a disperse medium proceeded smoothly to give the corresponding carbonyl compounds. The N-oxyl-immobilized silica gel 1 was prepared by silane-coupling method. Recycling of both the aqueous solution and the N-oxyl-immobilized silica gel 1 was performed successfully.

  在N-氧化氮固定化硅胶作为分散相、NaBr/NaHCO3水溶液作为分散介质的分散体系中，醇的电氧化反应顺利进行，得到了相应的羰基化合物。N-氧化氮固定化硅胶1是通过硅烷偶联法制备的。水溶液和N-氧化氮固定化硅胶1都成功实现了循环使用。
• Synthesis, biological evaluation and molecular modeling studies of psammaplin A and its analogs as potent histone deacetylases inhibitors and cytotoxic agents
  作者：Jiachen Wen、Yu Bao、Qun Niu、Jiang Liu、Jinyu Yang、Wanqiao Wang、Tao Jiang、Yinbo Fan、Kun Li、Jian Wang、Linxiang Zhao、Dan Liu

  DOI：10.1016/j.bmcl.2015.12.094

  日期：2016.9

  In this study, a concise synthetic method of psammaplin A was achieved from 3-bromo-4-hydroxybenzaldahyde and hydantoin through a four-step synthesis via Knoevenagel condensation, hydrolysis, oximation and amidation in 37% overall yield. A collection of novel psammaplin A analogs focused on the variations of substituents at the benzene ring and modifications at the oxime moiety were synthesized. Among

  在这项研究中，通过Knoevenagel缩合，水解，肟化和酰胺化的四步合成，由3-溴-4-羟基苯甲酰苯乙醛和乙内酰脲合成了一种简洁的psammaplin A合成方法，总收率为37％。合成了一组新的针对苯环上取代基的变化和肟部分上的修饰的新的psammaplin A类似物。在所有合成的化合物中，5d和5e显示出比psammaplin A更好的HDAC抑制作用，并且对四种癌细胞系（PC-3，MCF-7，A549和HL-60）具有相当的细胞毒性。分子对接和动力学模拟表明，（i）肟基团的氢原子通过水桥连氢键与HDAC1的Asp99相互作用，并且（ii）羟基在苯的对位上最佳连接，

表征谱图