1-溴-4-(甲基亚磺酰)苯 | 934-71-4

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酰卤化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-4-(甲基亚磺酰)苯
• 中文别名: 1-溴-4-(甲基亚磺酰基)苯
• 英文名称: 1-bromo-4-(methylsulfinyl)benzene
• 英文别名: 4-bromophenyl methyl sulfoxide；p-bromophenyl methyl sulfoxide；1-bromo-4-methanesulfinylbenzene；methyl p-bromophenyl sulfoxide；1-bromo-4-methylsulfinylbenzene
• CAS: 934-71-4
• 化学式: C₇H₇BrOS
• 分子量: 219.102
• InChiKey: MPOPDYTWAYBUOD-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80
• 沸点：
  319.4±25.0 °C(Predicted)
• 密度：
  1.68
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Bromo-4-(methylsulfinyl)benzene
Synonyms: 1-Bromo-4-methylsulfinylbenzene

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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-Bromo-4-(methylsulfinyl)benzene
CAS number: 934-71-4

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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: C7H7BrOS
Molecular weight: 219.1

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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, sulfur oxides.

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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

1-溴-4-(甲基亚磺酰)苯可以作为有机合成中间体和医药中间体，主要应用于实验室研发及化工生产过程。

反应信息

• 作为反应物：
  描述：

  1-溴-4-(甲基亚磺酰)苯 在 {MoO2Cl2(dmf)2} 、 甘油 作用下， 以92%的产率得到4-溴茴香硫醚
  参考文献：
  名称：

  An unprecedented use for glycerol: chemoselective reducing agent for sulfoxides

  摘要：

  甘油的一种新应用已得到证实，它不仅是一种绿色溶剂，还是一种高附加值产品的前体。简单、易得、环保的二氧钼（VI）络合物是利用这种生物质衍生化学原料进行化学选择性亚砜脱氧的高效催化剂。精炼甘油和粗甘油均可使用，从而扩大了这一反应的潜在应用范围。此外，还研究了甘油在这一还原过程中的后续转化。

  DOI：

  10.1039/c3gc36908k
• 作为产物：
  描述：

  4-甲氧基茴香硫醚 在 molybdenium(VI) dioxodichloride 双氧水 作用下， 以 水 、 丙酮 为溶剂， 反应 0.08h， 以95%的产率得到1-溴-4-(甲基亚磺酰)苯
  参考文献：
  名称：

  Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and a Mo(VI) salt as catalyst

  摘要：

  Selective oxidation of sulfides to sulfoxides and sulfones is achieved by H2O2 using MoO2Cl2 as the catalyst. Various substituted sulfides having functional groups Such as methyl, methoxy, bromo, nitro, alkene. alkyne, alcohol. ester, aldehyde and remarkably an oxime are successfully and selectively oxidized without affecting the sensitive functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.153

文献信息

• A nickel nanoparticle engineered CoFe₂O₄/SiO₂–NH₂@carboxamide composite as a novel scaffold for the oxidation of sulfides and oxidative coupling of thiols
  作者：Mina Zohrevandi、Roya Mozafari、Mohammad Ghadermazi

  DOI：10.1039/d1ra01592c

  日期：——

  particles on the surface. This compound was appropriately characterized using FT-IR spectroscopy, FE-SEM, ICP-OES, EDX, XRD, TGA analysis, VSM, and X-ray atomic mapping. The catalytic oxidation of sulfides and oxidative coupling of thiols in the presence of the designed catalyst was explored as a highly selective catalyst using hydrogen peroxide (H2O2) as a green oxidant. The easy separation, simple workup

  这项工作的目的是制备一种负载在CoFe 2 O 4纳米颗粒上的新型Ni-羧酰胺络合物（CoFe 2 O 4 /SiO 2 –NH 2 @carboxamide-Ni）。甲酰胺主体材料单元产生的空腔可以有效稳定镍纳米颗粒，并防止这些颗粒在表面聚集和分离。使用 FT-IR 光谱、FE-SEM、ICP-OES、EDX、XRD、TGA 分析、VSM 和 X 射线原子图谱对该化合物进行了适当表征。使用过氧化氢（H 2 O 2 ）作为绿色氧化剂，探索了在设计的催化剂存在下硫化物的催化氧化和硫醇的氧化偶联作为高选择性催化剂。该方案的一些突出优点是分离容易、后处理简单、纳米催化剂优异的稳定性、反应时间短、材料非爆炸性以及适当的产物收率。
• Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide
  作者：Ke-Si Du、Jing-Mei Huang

  DOI：10.1039/c7gc03864j

  日期：——

  A new route for a one-pot synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide using an electrochemical technique was developed. This protocol proceeded smoothly by employing electrons and hydrogen peroxide as clean oxidants, and a wide range of aromatic and aliphatic sulfoxides were synthesized in moderate to good yields.

  开发了一种使用电化学技术从苯酚/硫醇和二甲基亚砜一锅法合成甲基亚砜的新途径。该方案通过使用电子和过氧化氢作为清洁氧化剂而顺利进行，并以中等至良好的产率合成了多种芳族和脂族亚砜。
• Rh(I)-Catalyzed Arylation of Heterocycles via C−H Bond Activation:  Expanded Scope through Mechanistic Insight
  作者：Jared C. Lewis、Ashley M. Berman、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja0748985

  日期：2008.2.1

  A practical, functional group tolerant method for the Rh-catalyzed direct arylation of a variety of pharmaceutically important azoles with aryl bromides is described. Many of the successful azole and aryl bromide coupling partners are not compatible with methods for the direct arylation of heterocycles using Pd(0) or Cu(I) catalysts. The readily prepared, low molecular weight ligand, Z-1-tert-butyl-2

  描述了一种实用的、官能团耐受的方法，用于各种药学上重要的唑类与芳基溴化物的 Rh 催化直接芳基化。许多成功的唑和芳基溴偶联伙伴与使用 Pd(0) 或 Cu(I) 催化剂直接芳基化杂环的方法不兼容。容易制备的低分子量配体 Z-1-叔丁基-2,3,6,7-四氢膦以双齿 P-烯烃方式与 Rh 配位，提供高活性但热稳定的芳基化催化剂，是这种方法的成功至关重要。通过使用相应鏻的四氟硼酸盐，反应可以在手套箱外组装，无需纯化试剂或溶剂。反应也在四氢呋喃或二恶烷中进行，与大多数其他使用高沸点酰胺溶剂直接芳基化唑类的方法相比，这大大简化了产品的分离。反应在微波反应器中加热进行，在 2 小时内获得优异的产品收率。
• A novel, easy and mild preparation of sulfilimines from sulfoxides using the Burgess reagent
  作者：Sadagopan Raghavan、Shaik Mustafa、Kailash Rathore

  DOI：10.1016/j.tetlet.2008.04.152

  日期：2008.6

  A novel preparation of sulfilimines from the corresponding sulfoxides using the Burgess reagent is described. The reaction is general to dialkyl- and aryl alkyl sulfoxides and proceeds under mild conditions in benzene. A variety of protecting groups can be introduced on the nitrogen of the sulfilimine by choosing the appropriate Burgess reagent.

  描述了使用Burgess试剂从相应的亚砜制备亚硫亚胺的新方法。该反应通常为二烷基亚砜和芳基烷基亚砜，并在温和的条件下在苯中进行。通过选择合适的伯吉斯试剂，可以在硫亚胺的氮上引入各种保护基。
• 2-Iodylphenol Ethers:  Preparation, X-ray Crystal Structure, and Reactivity of New Hypervalent Iodine(V) Oxidizing Reagents
  作者：Alexey Y. Koposov、Rashad R. Karimov、Ivan M. Geraskin、Victor N. Nemykin、Viktor V. Zhdankin

  DOI：10.1021/jo0614947

  日期：2006.10.1

  2-Iodylphenol ethers were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenol ethers and isolated as chemically stable, microcrystalline products. Single-crystal X-ray diffraction analysis of 1-iodyl-2-isopropoxybenzene 8c and 1-iodyl-2-butoxybenzene 8d revealed pseudopolymeric arrangements in the solid state formed by intermolecular interactions between IO2 groups of different

  通过相应的2-碘苯酚醚的二甲基二环氧乙烷氧化制备2-碘苯酚醚，并分离为化学稳定的微晶产物。1-碘-2-异丙氧基苯8c和1-碘-2-丁氧基苯8d的单晶X射线衍射分析显示，固态的假聚合物排列是由不同分子的IO 2基团之间的分子间相互作用形成的。2-碘基苯酚醚可以将硫化物选择性氧化为亚砜，将醇选择性氧化为相应的醛或酮。

表征谱图