5-溴-2-戊酮 | 3884-71-7

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-溴-2-戊酮
• 中文别名: 2-羟基-3-溴苯甲酸
• 英文名称: bromo-5-pentanone-2
• 英文别名: 5-bromo-2-pentanone；5-Bromo-2-pentanon；5-bromopentan-2-one
• CAS: 3884-71-7
• 化学式: C₅H₉BrO
• mdl: MFCD00051425
• 分子量: 165.03
• InChiKey: HTKABMPGOHRVCT-UHFFFAOYSA-N

物化性质

• 沸点：
  73-75 °C(Press: 12 Torr)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  -20°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-pentan-2-one
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: 5-Bromo-pentan-2-one
CAS number: 3884-71-7

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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: C5H9BrO
Molecular weight: 165.0

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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

制备方法与用途

化学性质：

• 液体。
• 加热至188-190℃会分解，沸点为77℃（1.86kPa）。

用途： 医药中间体。

生产方法： 通过乙酰丙醇溴化获得。具体步骤如下：首先将溴化钠加入水中搅拌溶解，然后加入硫酸并控制温度在75℃下维持1小时后再加完。接着，在75-85℃下加入乙酰丙醇，并升温至90℃保持半小时。冷却至35℃后，再加水至20℃静置，分取有机相，用碳酸钠溶液中和至pH为7，静置后除去水层即可得到5-溴-2-戊酮。总收率为84%。

反应信息

• 作为反应物：
  描述：

  5-溴-2-戊酮 在 sodium hydroxide 、 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 5-已烯-2-酮
  参考文献：
  名称：

  Cornish Christopher A.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2585 - 2598

  摘要：

  DOI：
• 作为产物：
  描述：

  5-羟基-2-戊酮 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 5-溴-2-戊酮
  参考文献：
  名称：

  钛催化叔醇自由基脱羟基烷基化

  摘要：

  醇的脱氧自由基 CC 键形成反应是合成化学中长期存在的挑战，目前的方法依赖于多步骤程序。在此，我们报告了叔醇的直接脱羟基自由基烷基化反应。这一新协议显示了从醇类中生成叔碳自由基的可行性，并为轻松精确地构建全碳四元中心提供了一种方法。该反应在醇和活化烯烃的广泛底物范围内进行。它可以耐受各种亲电偶联伙伴，包括烯丙基羧酸盐、芳基和乙烯基亲电试剂以及伯烷基氯/溴化物，使该方法与交叉偶联程序形成互补。该方法对叔醇的烷基化具有高度选择性，保持仲醇/伯醇（包括苯甲醇）和酚类完好无损。该方法的合成效用因其 10 克规模的反应和复杂分子的后期修饰而突出。实验和 DFT 计算的组合建立了一个合理的机制，暗示通过 Ti 催化的 C-OH 键均裂产生叔碳自由基。

  DOI：

  10.1021/jacs.0c07492

文献信息

• Palladium-Catalyzed Aerobic Anti-Markovnikov Oxidation of Aliphatic Alkenes to Terminal Acetals
  作者：Saki Komori、Yoshiko Yamaguchi、Yasutaka Kataoka、Yasuyuki Ura

  DOI：10.1021/acs.joc.8b02919

  日期：2019.3.15

  Terminal acetals were selectively synthesized from various unbiased aliphatic terminal alkenes and 1,2-, 1,3-, or 1,4-diols using a PdCl2(MeCN)2/CuCl catalyst system in the presence of p-toluquinone under 1 atm of O2 and mild reaction conditions. The slow addition of terminal alkenes suppressed the isomerization to internal alkenes successfully. Electron-deficient cyclic alkenes, such as p-toluquinone

  在1 atm下在对甲苯醌存在下，使用PdCl 2（MeCN）2 / CuCl催化剂体系，由各种无偏的脂族末端烯烃和1,2-，1,3-或1,4-二醇选择性合成末端缩醛。O 2和温和的反应条件。末端烯烃的缓慢添加成功地抑制了异构化为内部烯烃。缺电子的环状烯烃，例如对甲苯醌，是增强催化活性和抗马尔科夫尼科夫选择性的关键添加剂。发现烯烃中的卤素基团起导向基团的作用，抑制了异构化并有效地提高了选择性。
• Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides
  作者：Chu-Ting Yang、Zhen-Qi Zhang、Hazmi Tajuddin、Chen-Cheng Wu、Jun Liang、Jing-Hui Liu、Yao Fu、Maria Czyzewska、Patrick G. Steel、Todd B. Marder、Lei Liu

  DOI：10.1002/anie.201106299

  日期：2012.1.9

  unprecedented copper‐catalyzed cross‐coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts=4‐toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means.

  易于获得：描述了标题化合物与乙硼试剂的前所未有的铜催化交叉偶联反应（参见方案； Ts = 4-甲苯磺酰基）。该反应可用于制备具有不同结构和官能团的伯烷基硼酸酯和仲烷基硼酸酯。生成的产品将很难通过其他方式访问。
• INTEGRIN INHIBITORS
  申请人：Morphic Therapeutic, Inc.

  公开号：EP3617206A1

  公开（公告）日：2020-03-04

  Disclosed are small molecule inhibitors of αvβ6 integrin, and methods of using them to treat a number of diseases and conditions.

  揭示了αvβ6整合素的小分子抑制剂，以及使用它们治疗多种疾病和症状的方法。
• Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases
  作者：Kathrin Heckenbichler、Anna Schweiger、Lea Alexandra Brandner、Alexandra Binter、Marina Toplak、Peter Macheroux、Karl Gruber、Rolf Breinbauer

  DOI：10.1002/anie.201802962

  日期：2018.6.11

  bearing an electron‐withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C−C bonds. α,β‐Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two‐electron‐reduced

  来自老黄酶 (OYE) 家族的烯还原酶可还原带有吸电子基团（例如羰基）的 α,β-不饱和化合物中的 C=C 双键。这种不对称还原已被用于生物催化。除了其典型功能之外，我们还发现该酶家族的成员还可以催化 C−C 键的形成。含有额外亲电基团的 α,β-不饱和醛和酮会发生还原环化。从机制上讲，双电子还原酶辅因子 FMN 传递氢化物以生成烯醇化物中间体，该中间体与内部亲电子试剂发生反应。用非质子 Phe 或 Trp 单位点取代关键的 Tyr 残基有利于环化反应而不是自然还原反应。新的转化使得对映选择性合成手性环丙烷的效率高达 >99% 。
• Ti-Catalyzed Straightforward Synthesis of Exocyclic Allenes
  作者：Juan Muñoz-Bascón、Carmen Hernández-Cervantes、Natalia M. Padial、Míriam Álvarez-Corral、Antonio Rosales、Ignacio Rodríguez-García、J. Enrique Oltra

  DOI：10.1002/chem.201304033

  日期：2014.1.13

  Exocyclic allenes constitute useful building blocks in organic synthesis and have recently been identified as key intermediates in the synthesis of natural products. Here the first general method for the most straightforward synthesis of exocyclic allenes reported to date is presented. This method is based on the Barbier‐type cyclization of propargyl halides catalyzed by titanium; a safe, abundant

  环外烯丙基是有机合成中有用的结构单元，最近被鉴定为天然产物合成中的关键中间体。这里介绍了迄今为止报道的最直接合成环外烯丙基的第一种通用方法。该方法基于钛催化的炔丙基卤化物的Barbier型环化。一种安全，丰富且环保的金属。该反应在与不同官能团兼容的温和条件下进行，并提供具有五环，六环和七元碳环以及带有环外亚丙基的含氮杂环的良好收率。还提供了支持提出的反应机理的实验证据。而且，该方法可以通过使用手性二茂钛（III）催化剂以对映选择性的方式进行。