4’-溴苯己酮 | 7295-46-7

• 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: 4’-溴苯己酮
• 中文别名: 4'-溴苯己酮；4-溴苯戊酮
• 英文名称: 1-(4-bromophenyl)hexan-1-one
• 英文别名: 1-(4-bromophenyl)-1-hexanone
• CAS: 7295-46-7
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: MVLMRPWLTMFPJI-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 ºC
• 沸点：
  322 ºC
• 密度：
  1.255
• 闪点：
  48 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(4-Bromophenyl)hexan-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)hexan-1-one
CAS number: 7295-46-7

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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: C12H15BrO
Molecular weight: 255.2

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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

用途

4'-溴苯己酮广泛应用于实验室研发和化工医药合成过程。

反应信息

• 作为反应物：
  描述：

  4’-溴苯己酮 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以0.86 g的产率得到4-己酰基苯胺
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides

  摘要：

  A number of structural analogues of the known toxicant para-aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 +/- 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.046
• 作为产物：
  描述：

  正戊基溴化镁 在 sodium dichromate 、 硫酸 作用下， 以 乙醚 、 水 为溶剂， 反应 3.33h， 生成 4’-溴苯己酮
  参考文献：
  名称：

  基于有机铜偶联物与双环偶氮烯的对映选择性合成卡巴前列环素类似物的新策略及其在合成 13,14-Dinor-inter-p-亚苯基卡巴环素中的应用

  摘要：

  E/Z-13,14-dinor-inter-p-phenylene carbacyclin (E/Z-2d) 的对映选择性合成已经实现，有望作为卡巴前列环素类似物的一般路线。该合成中的关键中间体是双环偶氮烯 Ts-9，关键步骤是手性芳基铜化合物 Cu-8d/Pn-Bu3 与偶氮烯的区域和立体选择性共轭加成，形成腙7d。从酮 4 对映选择性合成 95% ee 的偶氮烯 Ts-9 分别分四步和五步完成。因此，双环酮 4 与手性碱 Li-10 的对映选择性去质子化和用 ClSiMe3 捕获烯醇锂 11 得到烯醇醚 12，将其用 N-氯琥珀酰亚胺 (NCS) 氯化得到氯酮 13。或者，氯酮 13 也在 11 用 NCS 氯化后制备。氯酮 13 转化为氯腙 14，在用弱碱处理后提供偶氮 Ts-9。98% ee 的芳基铜化合物 8d 由醇 16 分两步获得，醇 16 是通过用 (-)-二异松蒎基氯硼烷对映选择性还原酮

  DOI：

  10.1021/ja0125772

文献信息

• Iron-Catalyzed C–C Single-Bond Cleavage of Alcohols
  作者：Wei Liu、Qiang Wu、Miao Wang、Yahao Huang、Peng Hu

  DOI：10.1021/acs.orglett.1c03137

  日期：2021.11.5

  An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C–C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a

  铁催化的醇通过 C-C 键断裂的解构/氢化反应通过光催化发展，以产生酮或醛作为产物。带有广泛取代基的叔醇、仲醇和伯醇是合适的底物。复杂的天然醇也可以选择性地进行转化。对该机制的研究揭示了在 2,4,6-可力丁的帮助下，氯自由基改善 O-H 均裂的过程。
• Acyl hydrazides as acyl donors for the synthesis of diaryl and aryl alkyl ketones
  作者：Ahmed R. Akhbar、Vijay Chudasama、Richard J. Fitzmaurice、Lyn Powell、Stephen Caddick

  DOI：10.1039/c3cc47967f

  日期：——

  In this communication we describe a novel strategy for the formation of valuable diaryl and aryl alkyl ketones from acyl hydrazides. A wide variety of ketones are prepared and the mild reaction conditions allow for the use of a range of functionalities, especially in the synthesis of diaryl ketones.

  在本交流中，我们描述了一种从酰基酰肼形成有价值的二芳基和芳基烷基酮的新策略。制备了各种各样的酮，并且温和的反应条件允许使用多种功能，特别是在二芳基酮的合成中。
• THERAPEUTIC COMPOUNDS
  申请人：Old David W.

  公开号：US20090227635A1

  公开（公告）日：2009-09-10

  Compounds comprising or a pharmaceutically acceptable salt or a prodrug thereof, are disclosed, wherein Y, A, B, and J are as described. Methods, compositions, and medicaments related thereto are also disclosed.

  包含Y、A、B和J的化合物或其药用可接受的盐或前药，已被披露。还披露了与之相关的方法、组合物和药物。
• Aquapalladium Complex: A Stable and Convenient Catalyst for the Intermolecular Hydroamination of Alkynes
  作者：Tomohiro Shimada、Gan�B. Bajracharya、Yoshinori Yamamoto

  DOI：10.1002/ejoc.200400568

  日期：2005.1

  The intermolecular hydroamination of alkynes proceeds very smoothly in the presence of a catalytic amount of the aquapalladium complex [Pd(dppe)(H2O)2](TfO)2. This reaction most probably proceeds through the formation of an equilibrium between the hydroxopalladium and the amidopalladium complexes, and subsequent aminopalladation of alkynes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  在催化量的水钯配合物 [Pd(dppe)(H2O)2](TfO)2 存在下，炔烃的分子间加氢胺化反应非常顺利。该反应最有可能通过在羟基钯和酰胺钯配合物之间形成平衡以及随后炔烃的氨基钯化来进行。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• A New and One-Pot Synthesis of α,β-Unsaturated Ketones by Dehydrogenation of Various Ketones with<i>N-tert</i>-Butyl Phenylsulfinimidoyl Chloride
  作者：Teruaki Mukaiyama、Jun-ichi Matsuo、Hideo Kitagawa

  DOI：10.1246/cl.2000.1250

  日期：2000.11

  α,β-Unsaturated ketones were synthesized by one-pot procedure from various ketones in good to excellent yields on treatment of their lithium enolates with N-tert-butyl phenylsulfinimidoyl chloride (1) under mild conditions.

  在温和条件下用 N-叔丁基苯基亚磺酰亚胺酰氯 (1) 处理其烯醇锂，通过一锅法从各种酮合成 α,β-不饱和酮，收率良好至极好。