2'-氯-4-溴苯乙酮 | 4209-02-3

• 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: 2'-氯-4-溴苯乙酮
• 中文别名: 1-(4-溴苯基)-2-氯-1-乙酮；2-氯-4'-溴苯乙酮；α-氯代-4-溴苯乙酮；Alpha-氯代-4-溴苯乙酮
• 英文名称: 1-(4-bromophenyl)-2-chloroethan-1-one
• 英文别名: 1-(4-bromophenyl)-2-chloroethanone；p-bromophenacyl chloride；4-bromophenacyl chloride；2-chloro-1-(4-bromophenyl)ethan-1-one；1-(4-bromophenyl)-2-chloro-1-one；2-chloro-4'-bromoacetophenone
• CAS: 4209-02-3
• 化学式: C₈H₆BrClO
• mdl: MFCD00095178
• 分子量: 233.492
• InChiKey: HCQNNQFCUAGJBD-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  306.7±22.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 海关编码：
  2914700090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P260,P264,P270,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P363,P405,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloro-4’-bromoacetophenone
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: 2-Chloro-4’-bromoacetophenone
CAS number: 4209-02-3

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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, refrigerated.
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: C8H6BrClO
Molecular weight: 233.5

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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 chloride, 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：

  2'-氯-4-溴苯乙酮 在 azide on Amberlite(R) IRA 900 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-叠氮基-1-(4-溴苯基)乙酮
  参考文献：
  名称：

  使用聚合物支持的试剂快速制备邻位叠氮基醇的步骤

  摘要：

  使用大孔离子交换树脂上负载的试剂，从芳基α-卤代酮开始，以高至高收率和高纯度制备了几种邻位叠氮基醇。这是制备芳基叠氮醇的一种快速而新的方法。

  DOI：

  10.1016/j.tetlet.2005.05.023
• 作为产物：
  描述：

  4-溴苯乙酮 在 N-氯代丁二酰亚胺 、 对甲苯磺酸 作用下， 生成 2'-氯-4-溴苯乙酮
  参考文献：
  名称：

  级联三硫自由基（S 3 •–）加成/电子脱甲苯磺酸合成1,2,3-噻二唑和异噻唑

  摘要：

  已经开发了三硫自由基阴离子（S 3 •–）与原位形成的偶氮烯烃和α，β-过饱和的N-磺酰亚胺类化合物介导的反应，用于构建1,2,3-噻二唑和异噻唑。S 3 •–是由DMF中的硫化钾原位生成的。这两种方法提供了一种新的，安全的和简单的方法来以高收率构建4-取代的1,2,3-噻二唑，5-取代的1,2,3-噻二唑和异噻唑。反应包括在温和条件下通过S 3 •加成形成新的C–S和N–S键和电子脱甲苯基化反应。

  DOI：

  10.1021/acs.joc.8b01450

文献信息

• Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of<i>N</i>-Phenylamidines with α-Cl Ketones
  作者：Jianhui Zhou、Jian Li、Yazhou Li、Chenglin Wu、Guoxue He、Qiaolan Yang、Yu Zhou、Hong Liu

  DOI：10.1021/acs.orglett.8b03383

  日期：2018.12.7

  versatile 3-acylindoles through Rh(III)-catalyzed C–H activation and annulation cascade of N-phenylamidines with α-Cl ketones was developed, in which α-Cl ketones serve as unusual one-carbon (sp3) synthons. This strategy features high regioselectivity, efficiency, wide substrate tolerance, and mild reaction conditions, which further underscore its synthetic utility in drug molecule synthesis.

  在本研究中，开发了一种新的合成策略，可通过Rh（III）催化的C–H活化和N-苯基am与α-Cl酮的环合级联反应直接生产通用的3-acylindoles ，其中α-Cl酮用作不寻常的一碳（sp 3）合成子。该策略具有较高的区域选择性，效率，宽的底物耐受性和温和的反应条件，这进一步强调了其在药物分子合成中的合成效用。
• Promoting charge separation in donor–acceptor conjugated microporous polymers <i>via</i> cyanation for the photocatalytic reductive dehalogenation of chlorides
  作者：Weijie Zhang、Jiyong Deng、Zhengjun Fang、Donghui Lan、Yunfeng Liao、Xiang Zhou、Qingquan Liu

  DOI：10.1039/d1cy01386f

  日期：——

  Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier

  共轭微孔聚合物（CMPs）由于其结构可设计性和功能多功能性，已成为有前途的有机转化多相光催化剂。然而，受光生激子分离不充分的限制，其光催化效率远低于预期。在此，我们展示了一种氰化策略，通过选择性地将咔唑和氰基分别作为供电子和吸电子单元来促进 CMP 中的电荷载流子分离。由此产生的 CMP 具有 π 扩展的供体 (D)-受体 (A) 共轭结构，赋予它们独特的半导体特性，其中促进了有效的电荷分离和转移以及广泛的可见光吸收。与无氰对应物相比，氰基官能化的 CMP 显示出优异的光催化效率，例如氯化物的光催化还原脱卤。更突出的是，所设计的 CMP 的完全可回收性以及至少 10 次运行的催化活性而不会损失在氯化物的光催化还原脱卤中的催化性能，这证明了它们的稳健性和可持续性。
• Carbon-13 NMR spectra of some 4-substituted phenacyl chlorides and iodides
  作者：Paulo Roberto Olivato、Sandra Alvarez Guerrero、Roberto Rittner

  DOI：10.1002/mrc.1260250218

  日期：1987.2

  The 13 NMR singles for some 4‐substituted phenacylchlorides and iodides were assigned. The carbonyl carbons exhibit upfield shifts compared with those of the corresponding 4‐substituted acetophenones; in the chlorinated derivatives a downfield shift is observed for the α‐methylene carbons, while a reverse effect occurs in the iodinated compounds. The chemical shifts of the aromatic ring carbons are

  指定了一些 4 取代苯甲酰氯和碘化物的 13 NMR 单峰。与相应的 4-取代苯乙酮相比，羰基碳表现出高场位移；在氯化衍生物中观察到α-亚甲基碳的低场位移，而在碘化化合物中发生相反的作用。芳环碳的化学位移与使用取代基化学位移计算的那些非常一致。
• Microwave assisted fluorination: an improved method for side chain fluorination of substituted 1-arylethanones
  作者：Thor Håkon Krane Thvedt、Erik Fuglseth、Eirik Sundby、Bård Helge Hoff

  DOI：10.1016/j.tet.2009.09.070

  日期：2009.11

  microwave (MW) assisted fluorination of 1-arylethanones to their corresponding 1-aryl-2-fluoroethanones has been developed. The first step utilises Selectfluor™ as a fluorinating agent in methanol forming 1-aryl-2-fluoroethanones and their corresponding dimethyl acetals. In the second step, water is added and Selectfluor™ acts as a Lewis acid in the hydrolytic cleavage of the dimethyl acetals. Compared to

  已经开发了一种两步一锅微波（MW）辅助将1-蒽酮氟化为相应的1-芳基-2-氟乙酮的方法。第一步利用Selectfluor™作为甲醇中的氟化剂，形成1-芳基-2-氟乙酮及其相应的二甲基乙缩醛。在第二步中，添加水，并且Selectfluor™在二甲基乙缩醛的水解裂解中充当路易斯酸。与热合成相比，MW辅助方法可减少氟化反应和二甲基乙缩醛反应的反应时间。而且，一锅法减少了试剂和溶剂的消耗。该方法最适合于制备含有可钝化亲电芳族取代基的取代基的1-芳基-2-氟乙酮，但高度缺电子的酮如1-（3，5-二硝基苯基）乙酮反应更慢。使用富含电子的芳族酮进行的反应具有较低的区域选择性，并且还产生了氟代芳族产物。
• Silver(I)‐ and Base‐Mediated formal [4+3] Cycloaddition of <i>in Situ</i> generated 1,2‐Diaza‐1,3‐dienes with <i>C,N</i> ‐Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives
  作者：Zefei Li、Shuaikang Li、Tianjiao Kan、Xinyue Wang、Xin Xin、Yunlei Hou、Ping Gong

  DOI：10.1002/adsc.202000398

  日期：2020.7.16

  A silver(I)‐ and base‐mediated formal [4+3] cycloaddition reaction of in situ generated 1,2‐diaza‐1,3‐dienes with in situ formed C,N‐cyclic azomethine imines has been developed. This protocol provided an efficient method for the synthesis of biologically important 1,2,4,5‐tetrazepine derivatives with a wild substrate scope and excellent functional group tolerance in moderate to excellent yields.

  已经开发了一种由银（I）和碱介导的正式[4 + 3]环加成反应，该反应原位生成了1,2-二氮杂1,3-二烯与原位形成的C，N-环偶氮甲亚胺。该方案提供了一种有效的方法，用于合成具有重要底物范围和出色的官能团耐受性（中等至优异的产率）的重要的1,2,4,5-四氮杂pine生物衍生物。

表征谱图