苯基-4-溴苯磺酸 | 5455-14-1

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 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: 苯基-4-溴苯磺酸
• 英文名称: phenyl 4-bromobenzenesulfonate
• CAS: 5455-14-1
• 化学式: C₁₂H₉BrO₃S
• 分子量: 313.172
• InChiKey: ARYXAYIIDXKEDB-UHFFFAOYSA-N

物化性质

• 熔点：
  115.5 °C
• 沸点：
  415.5±37.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2906299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Phenyl 4-bromobenzenesulfonate
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: Phenyl 4-bromobenzenesulfonate
CAS number: 5455-14-1

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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: C12H9BrO3S
Molecular weight: 313.2

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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, 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

反应信息

• 作为反应物：
  描述：

  苯基-4-溴苯磺酸 在 1,1'-双(二苯基膦)二茂铁 、 bis(acetylacetonato)palladium(II) 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以86%的产率得到联苯
  参考文献：
  名称：

  钯在室温下通过裂解C‑O键的方式催化芳基磺酸盐的还原均偶联反应

  摘要：

  在温和条件下已成功实现了钯催化的芳基磺酸盐还原均偶联反应。这种转变是芳基磺酸盐在室温下通过C-O键断裂的均偶联反应的新方法，从而提供了对称性联芳基的另一种合成方法。所报道的还原性均偶联反应对许多常见的官能团均具有耐受性，而与给电子或吸电子性质无关，这使得这种新近发展的转变对于补充乌尔曼偶联很重要。

  DOI：

  10.1002/aoc.3705
• 作为产物：
  描述：

  钠盐 、 苯酚 以 水 、 乙腈 为溶剂， 反应 2.0h， 以98%的产率得到苯基-4-溴苯磺酸
  参考文献：
  名称：

  苯酚与芳烃亚磺酸钠的实用电氧化磺酰化生成芳基磺酸酯

  摘要：

  已经通过电氧化开发了一种实用且可持续的芳基磺酸酯合成方法。该反应使用稳定且容易获得的苯酚和芳基亚磺酸钠作为起始材料，在温和的反应条件下进行，无需额外的氧化剂。包括那些带有官能团的芳基磺酸酯以良好至极好的产率生产。该反应也可以在不降低反应效率的情况下以克级进行。这些结果很好地证明了该反应在有机合成中的潜在合成价值。

  DOI：

  10.1021/acs.joc.1c00260

文献信息

• Palladium-catalysed direct heteroarylation of bromobenzenes bearing SO2R substituents at C2 or C4
  作者：Charles Beromeo Bheeter、Rongwei Jin、Jitendra K. Bera、Henri Doucet

  DOI：10.1039/c3ra40769a

  日期：——

  Palladium-catalysed direct arylation of 4- or 2-bromobenzenesulfonic acid derivatives in the presence of a variety of heteroaromatics was found to proceed using 0.1–0.5 mol% palladium acetate as the catalyst. However, both the nature and position of the SO2R substituent on such bromobenzenes has an influence on the reaction rates and yields. The presence of SO2Et or SO2NEt2 at the C2 or C4 position of bromobenzene is tolerated. Good results were also obtained from bromobenzene substituted at C4 by SO2NHPh or SO2OPh. On the other hand, the reactions of bromobenzenes bearing either SO2N(Me)CH2Ph or SO2OAr at C2 led in some cases to intramolecular reactions instead of the desired intermolecular couplings. Some reactions were performed in cyclopentyl methyl ether, which can be considered as a green solvent.

  使用0.1-0.5%摩尔的醋酸钯作为催化剂，在多种杂芳环存在下，发现钯催化的4-或2-溴苯磺酸衍生物的直接芳基化反应可以进行。然而，溴苯上SO2R取代基的性质和位置对反应速率和产率有影响。在溴苯的C2或C4位置存在SO2Et或SO2NEt2是可以容忍的。在C4位置由SO2NHPh或SO2OPh取代的溴苯也得到了良好的结果。另一方面，在C2位置带有SO2N(Me)CH2Ph或SO2OAr的溴苯的反应在某些情况下会导致分子内反应，而不是所期望的分子间偶联。一些反应在环戊基甲基醚中进行，这种溶剂可以被认为是一种环保溶剂。
• SuFEx Reactions of Sulfonyl Fluorides, Fluorosulfates, and Sulfamoyl Fluorides Catalyzed by N-Heterocyclic Carbenes
  作者：Muze Lin、Jinyun Luo、Yu Xie、Guangfen Du、Zhihua Cai、Bin Dai、Lin He

  DOI：10.1021/acscatal.3c03820

  日期：2023.11.17

  Sulfur(VI) fluoride exchange (SuFEx) click chemistry provides a powerful tool for the rapid assembly of modular connections. Herein, we report an organocatalytic SuFEx reaction of sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides. Under the catalysis of 10 mol % N-heterocyclic carbene (NHC), or under the relay catalysis of NHC and HOBt, different SuFExable hubs efficiently undergo click reactions

  硫 (VI) 氟化物交换 (SuFEx) 点击化学为快速组装模块化连接提供了强大的工具。在此，我们报道了磺酰氟、氟硫酸盐和氨磺酰氟的有机催化 SuFEx 反应。在10 mol% N-杂环卡宾（NHC）的催化下，或在NHC和HOBt的中继催化下，不同的SuFExable中心可以有效地与醇或胺发生点击反应，生成磺酸盐、磺酰胺、硫酸盐、氨基磺酸盐和磺酰胺49 –99% 的收益率。通过该方法已制备了190多种磺酰化产物，其中包括25种天然产物衍生物。机理研究表明，NHCs 可能充当以碳为中心的布朗斯台德碱，通过形成氢键来活化醇或胺。
• 一种磺酸酯类化合物及其合成方法
  申请人：海南大学

  公开号：CN115557861A

  公开（公告）日：2023-01-03

  本发明揭示了一类磺酸酯类化合物及其合成法，该方法以苯酚衍生物和苯亚磺酸钠为主要原料，乙腈和水为溶剂，使用2当量四丁基碘化铵，在25℃的环境下15 mA有效反应2小时,较高产率得到磺酸酯类化合物。本方法具有成本较低，产率高，操作简便、无污染等优点，具有潜在的工业应用前景。该方法为磺酸酯类化合物的制备提供了一条廉价、绿色的途径。
• Concise Formation of 4-Benzyl Piperidines and Related Derivatives Using a Suzuki Protocol
  作者：Susan Vice、Tom Bara、Annette Bauer、C. Anderson Evans、Jennifer Ford、Hubert Josien、Stuart McCombie、Michael Miller、Dennis Nazareno、Anandan Palani、Jay Tagat

  DOI：10.1021/jo0007682

  日期：2001.4.1
• Vizgert, R.V.; Maksimenko, N.N.; Rubleva, L.I., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 11, p. 2144 - 2146
  作者：Vizgert, R.V.、Maksimenko, N.N.、Rubleva, L.I.

  DOI：——

  日期：——