4-溴-n-苯基苯磺酰胺 | 7454-54-8

• 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: 4-溴-n-苯基苯磺酰胺
• 中文别名: 4-溴-N-苯基苯磺酰胺
• 英文名称: 4-bromo-N-phenylbenzenesulfonamide
• 英文别名: 4-Brom-benzolsulfonsaeure-anilid；N-phenyl-S-(4-bromophenyl) sulfonamide
• CAS: 7454-54-8
• 化学式: C₁₂H₁₀BrNO₂S
• 分子量: 312.187
• InChiKey: ZCUJCYISOKHAAW-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  420.8±47.0 °C(Predicted)
• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 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: 4-Bromo-N-phenylbenzenesulfonamide
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: 4-Bromo-N-phenylbenzenesulfonamide
CAS number: 7454-54-8

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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: C12H10BrNO2S
Molecular weight: 312.2

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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, nitrogen oxides, 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：

  4-溴-n-苯基苯磺酰胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 28.0h， 生成 ethyl 1-(4-bromophenyl)sulfonyl-3-(2,2-dimethylpropyl)-2H-indole-3-carboxylate
  参考文献：
  名称：

  Alkoxyamine-Mediated Radical Synthesis of Indolinones and Indolines

  摘要：

  [GRAPHICS]Thermolysis of alpha-alkoxyamino propionanilides produces indolinones, whereas thermal reaction of N-allylaniline derivatives with various Tordo-type alkoxyamines results in formation of indolines in the radical regime.

  DOI：

  10.1021/ol0358049
• 作为产物：
  描述：

  4-溴苯磺酰氯 在 sodium isocyanate 、 三甲胺 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 4-溴-n-苯基苯磺酰胺
  参考文献：
  名称：

  磁性壳聚糖负载二甲双胍-Cu (II)配合物作为伯磺酰胺N-芳基化可回收催化剂的合成

  摘要：

  壳聚糖作为一种天然高分子和有效载体而备受关注，其应用具有生物降解性和生物相容性等诸多优点。在这项研究中，通过固定结构明确的二甲双胍与（3-氯丙基）三甲氧基硅烷 (TMOS) 的长尾，将铜配合物固定在带有二甲双胍的磁性壳聚糖配体上。合成的 Fe 3 O 4 -壳聚糖@二甲双胍-Cu(II) 配合物 (Fe 3 O 4 -CS@Met-Cu(II)) 在N- 伯磺酰胺的不同衍生物与芳基硼酸在乙醇中的芳基化。伯磺酰胺是由磺酰氯与氰酸钠在超声波照射下在水中反应制备的。在 EtOH 中利用多种底物作为绿色溶剂，初级和次级磺酰胺的产率高，易于处理以及催化剂的出色回收率和可重复使用性，使该过程成为一种简单、经济且环境友好的方法。合成的Fe 3 O 4-CS@Met-Cu(II) 使用各种技术进行表征，例如 XRD（X 射线衍射）、EDS（能量色散 X 射线光谱）、元素映射、TEM（透射电子显微镜）、FE

  DOI：

  10.1016/j.jorganchem.2021.121915
• 作为试剂：
  描述：

  二氢吡啶 、 1,3-dioxoisoindolin-2-yl bicyclo[1.1.1]pentane-1-carboxylate 在 (-)-1,2-双((2R,5R)-2,5-二甲基磷杂环戊烷)苯(1,5-环辛二烯)三氟甲磺酸铑(I) 、 4-溴-n-苯基苯磺酰胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以5.5%的产率得到diethyl 4-(bicyclo[1.1.1]pentan-1-yl)-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  电子供体-受体复合物光活化使镍催化双环[1.1.1]戊基自由基的脱羧交叉偶联

  摘要：

  使用双环 [1.1.1] 戊烷 (BCP) 作为对-二取代芳基生物等排体在药物开发计划中获得了相当大的动力。通过过渡金属介导的交叉偶联形成碳-碳键代表了一种有吸引力的策略来生成用于后期功能化的 BCP-芳基化合物，但这些通常需要反应性有机金属来根据需要从 [1.1.1] 螺旋桨制备 BCP 亲核试剂。在这项研究中，报道了通过光活性电子供体-受体复合物的作用，用（杂）芳基溴化物合成和 Ni 催化的 BCP 氧化还原活性酯的官能化。

  DOI：

  10.1021/acs.orglett.1c01558

文献信息

• 一种超声辅助合成N-芳基磺酰胺的方法
  申请人：中南大学

  公开号：CN108822002B

  公开（公告）日：2020-05-05

  本发明公开了一种超声辅助合成N‑芳基磺酰胺的方法。在超声搅拌条件下，以芳香硝基化合物、磺酰氯，铁粉为原料，通过硝基还原/磺酰氯还原/磺酰胺化串联反应，得到N‑芳基磺酰胺化合物。反应中水同时作为反应介质和氢源。该方法原料廉价易得，反应条件简便、温和、绿色节能，反应选择性及产率高，底物官能团兼容性优异，具有较高的应用价值。
• Synthesis of <i>N</i>-arylsulfonamides <i>via</i> Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium
  作者：Jun Jiang、Sheng Zeng、De Chen、Chaozhihui Cheng、Wei Deng、Jiannan Xiang

  DOI：10.1039/c8ob01172a

  日期：——

  A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust was the sole reductant in the transformation and it can be easily performed on a large scale.

  一种引人入胜的Fe促进的合成N-芳基磺酰胺的方案已经被开发出来。从商业上可得的硝基苯和磺酰氯出发，可以得到中等至极好的相应N-芳基磺酰胺的产率。特别是，Fe粉尘是转换中的唯一还原剂，且可以轻松地大规模进行。
• Copper-catalyzed synthesis of sulfonamides from nitroarenes <i>via</i> the insertion of sulfur dioxide
  作者：Xuefeng Wang、Min Yang、Yunyan Kuang、Jin-Biao Liu、Xiaona Fan、Jie Wu

  DOI：10.1039/d0cc00721h

  日期：——

  Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino

  硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。
• Small Molecule Disruptors of the Glucokinase–Glucokinase Regulatory Protein Interaction: 3. Structure–Activity Relationships within the Aryl Carbinol Region of the <i>N</i>-Arylsulfonamido-<i>N</i>′-arylpiperazine Series
  作者：Nobuko Nishimura、Mark H. Norman、Longbin Liu、Kevin C. Yang、Kate S. Ashton、Michael D. Bartberger、Samer Chmait、Jie Chen、Rod Cupples、Christopher Fotsch、Joan Helmering、Steven R. Jordan、Roxanne K. Kunz、Lewis D. Pennington、Steve F. Poon、Aaron Siegmund、Glenn Sivits、David J. Lloyd、Clarence Hale、David J. St. Jean

  DOI：10.1021/jm5000497

  日期：2014.4.10

  report the results of our expanded SAR investigations that focused on modifications to the aryl carbinol group of this series. Guided by the X-ray cocrystal structure of compound 1 bound to hGKRP, we identified several potent GK–GKRP disruptors bearing a diverse set of functionalities in the aryl carbinol region. Among them, sulfoximine and pyridinyl derivatives 24 and 29 possessed excellent potency

  我们最近报道了一种通过将小分子与其内源性抑制剂葡萄糖激酶调节蛋白（GKRP）结合来增加胞质葡萄糖激酶（GK）水平的新方法。这些初步研究最终确定了2-（4-（（2 S）-4-（（6-6-氨基-3-吡啶基）磺酰基）-2-（1-丙炔-1-基）-1-哌嗪基）。苯基）-1,1,1,1,3,3,3-六氟-2-丙醇（1，AMG-3969），一种有效增强糖尿病动物GK转运并降低血糖水平的化合物。在这里，我们报告了我们扩大的SAR研究的结果，这些研究集中于对该系列芳基甲醇基团的修饰。遵循化合物1的X射线共晶结构绑定到hGKRP，我们确定了几种有效的GK-GKRP破坏者，在芳基甲醇区域具有多种功能。其中，亚磺酰亚胺和吡啶基衍生物24和29具有优异的效力以及良好的PK性能。当在db / db小鼠中口服给药时，两种化合物均可显着降低进食的血糖水平（最高58％）。
• Palladium-Catalyzed Cascade sp² C–H Bond Functionalizations Allowing One-Pot Access to 4-Aryl-1,2,3,4-tetrahydroquinolines from <i>N</i>-Allyl-<i>N</i>-arylsulfonamides
  作者：Kedong Yuan、Jean-François Soulé、Vincent Dorcet、Henri Doucet

  DOI：10.1021/acscatal.6b02586

  日期：2016.12.2

  palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)–C(sp3) bonds were formed via activation of C(sp2)–H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents

  我们已经开发了钯催化的级联反应，可以从N-烯丙基-N-芳基磺酰胺和苯磺酰氯有效合成4-芳基-1,2,3,4-四氢喹啉。在此转换中，通过激活C（sp 2）-H键形成了两个C（sp 2）-C（sp 3）键。该反应使用容易获得的催化剂PdCl 2进行，其中Li 2 CO 3为廉价的碱，CuBr为添加剂，并且在两个反应伙伴上都可以耐受多种取代基。

表征谱图