1-(4-溴苯基)-2-甲基丙烷-1-酮 | 49660-93-7

• 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: 1-(4-溴苯基)-2-甲基丙烷-1-酮
• 英文名称: 4'-bromoisobutyrophenone
• 英文别名: 1-(4-bromophenyl)-2-methylpropan-1-one；1-(4-bromophenyl)-2-methyl-1-propanone
• CAS: 49660-93-7
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: PMFLKZHWZXWOEH-UHFFFAOYSA-N

物化性质

• 熔点：
  18°C(lit.)
• 沸点：
  87°C/3mmHg(lit.)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 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-(4-Bromophenyl)-2-methylpropan-1-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: 1-(4-Bromophenyl)-2-methylpropan-1-one
CAS number: 49660-93-7

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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: C10H11BrO
Molecular weight: 227.1

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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-(4-溴苯基)-2-甲基丙烷-1-酮 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 L-脯氨酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 74.0h， 生成 3-hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-one
  参考文献：
  名称：

  一种非罗考昔及其中间体的合成方法

  摘要：

  本发明涉及药物合成领域，提供了一种非罗考昔及其中间体的合成方法。该非罗考昔中间体的合成方法，以对溴苯丙酮为起始原料，避免使用环境不友好的硫醚作为起始原料，对溴苯丙酮与甲基化试剂进行甲基化反应得到第一中间体；第一中间体经亚磺化反应直接获得第二中间体，将硫化反应和氧化反应缩短为一步取代反应，极大地简化了反应步骤，缩短了反应时间，提高了反应效率。同时，本发明还采用NBS体系，使第二中间体羟基化反应直接得到非罗考昔中间体，环境更友好，适合大规模生产，提高了反应速率。此外，该非罗考昔的合成方法包括上述非罗考昔中间体的合成方法，其能以反应条件更温和、环境更友好的方式合成非罗考昔。

  公开号：

  CN107686471B
• 作为产物：
  描述：

  异丁基苯 在 Oxone 、 sodium bromide 作用下， 以 水 、 乙腈 为溶剂， 以30%的产率得到1-(4-溴苯基)-2-甲基丙烷-1-酮
  参考文献：
  名称：

  烷基苯的双氧化/溴化

  摘要：

  在溴化钠和Oxone的存在下，一系列烷基苯衍生物被溴化和/或氧化，最多可官能化四个CH键。

  DOI：

  10.1016/j.tetlet.2016.01.062

文献信息

• α-羟基酮化合物的廉价高效合成方法
  申请人：北京大学

  公开号：CN104710256B

  公开（公告）日：2017-03-22

  本发明公开了一种α‑羟基酮化合物的廉价高效合成方法。该合成方法包括：在常压条件下，以碘单质、N‑溴代丁二酰亚胺、溴化铜、溴单质、溴化氢、N‑碘代丁二酰亚胺或碘化氢作为催化剂，以亚砜为氧化剂，以水或亚砜为羟基源，以亚砜，乙酸乙酯、N,N‑二甲基甲酰胺、乙腈、甲苯、1,4‑二氧六环、1,2‑二氯乙烷、四氢呋喃或H2O为溶剂，与羰基化合物混合于10‑120℃温度下进行氧化羟基化反应即可将羰基化合物高选择性的转化为α‑羟基酮化合物。本发明方法与传统合成方法相比具有操作简单，收率高，条件简单，易于纯化，废弃物排放量少，反应设备简单，易于工业化生产等诸多优点。本发明的方法具有广泛地适用性，能够用于多种α‑羟基酮化合物的合成。
• <i>i</i>-Pr₂NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions
  作者：Kilian Colas、A. Catarina V. D. dos Santos、Abraham Mendoza

  DOI：10.1021/acs.orglett.9b02899

  日期：2019.10.4

  preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation

  由羧酸根阴离子直接制备酮受到有机锂试剂或需要独立制备的活化酰基源的使用的极大限制。在本文中，使用特定的酰胺化镁添加剂来激活和控制更具耐受性的格利雅试剂的添加以使阴离子羧酸化。这种策略可以在一次操作中从CO 2模块化合成酮，并制备同位素标记的药物结构单元。
• Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products
  作者：Louis K. M. Chan、Darren L. Poole、Di Shen、Mark P. Healy、Timothy J. Donohoe

  DOI：10.1002/anie.201307950

  日期：2014.1.13

  The rhodium‐catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen‐borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form α‐branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a

  使用甲醇作为甲基化剂和借氢方法完成了铑催化的酮的甲基化。该序列的显着之处在于所需的温度相对较低，并且反应系统能够轻松形成 α 支化产物。双烷基化酮可以通过使用连续的一锅铱和铑催化工艺由甲基酮和两种不同的醇制备。
• CC Coupling of Ketones with Methanol Catalyzed by a N-Heterocyclic Carbene-Phosphine Iridium Complex
  作者：Xu Quan、Sutthichat Kerdphon、Pher G. Andersson

  DOI：10.1002/chem.201405990

  日期：2015.2.23

  carbene–phosphine iridium complex system was found to be a very efficient catalyst for the methylation of ketone via a hydrogen transfer reaction. Mild conditions together with low catalyst loading (1 mol %) were used for a tandem process which involves the dehydrogenation of methanol, CC bond formation with a ketone, and hydrogenation of the new generated double bond by iridium hydride to give the

  N-杂环卡宾-膦铱络合物系统被发现是通过氢转移反应使酮甲基化的非常有效的催化剂。在串联过程中使用温和的条件，同时降低催化剂的负载量（1 mol％），该过程涉及甲醇的脱氢，与酮形成的CC键以及氢化铱将新生成的双键氢化以得到烷基化产物。使用这种铱催化剂体系，可以合成许多支链酮，转化率和收率都非常好。
• Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link
  作者：Hong-Lei Chen、Dian Wei、Jian-Wu Zhang、Cheng-Lin Li、Wei Yu、Bing Han

  DOI：10.1021/acs.orglett.8b00967

  日期：2018.5.18

  A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,γ- and γ-halo-γ,δ-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition

  开发了一种新的亚氨基自由基促进的二分体区域选择性5-exo-trig环化到乙烯基卤素/ 1,2-卤素自由基转移序列上，用于使用β-卤代-β，γ-和γ-卤代合成卤代甲基异恶唑/环硝酮-γ，δ-不饱和酮肟为底物，PhI（OAc）2 / TEMPO为氧化体系。DFT计算表明，卤代桥三元环跃迁态与1,2-Cl- / Br原子移位有关，而1,2-I原子迁移可通过消除/再分配机制加以考虑。指示迁移能力按以下顺序排列：I> Br> Cl。