N-(4-bromophenyl)-4-chlorobenzenesulfonamide | 2065-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-bromophenyl)-4-chlorobenzenesulfonamide
• 英文别名: 4-Chlor-benzolsulfon-N-(4-brom-phenyl)-amid
• CAS: 2065-38-5
• 化学式: C₁₂H₉BrClNO₂S
• 分子量: 346.632
• InChiKey: MHCWIXMBTKALBR-UHFFFAOYSA-N

物化性质

• 熔点：
  163 °C(Solv: ethanol (64-17-5))
• 沸点：
  445.1±55.0 °C(Predicted)
• 密度：
  1.677±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-4-chlorobenzenesulfonamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-(4-(6-bromopyrrolo[2,1-f][1,2,4]triazin-4-yl)phenyl)-4-chlorobenzenesulfonamide
  参考文献：
  名称：

  COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO KIT AND PDFGR

  摘要：

  这里描述了用于治疗与KIT和PDGFR相关疾病的化合物和组合物。

  公开号：

  US20170022206A1
• 作为产物：
  描述：

  4-氯苯磺酰胺 在 sodium hypochlorite 、 乙醇 、 potassium tert-butylate 、 copper diacetate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 56.0h， 生成 N-(4-bromophenyl)-4-chlorobenzenesulfonamide
  参考文献：
  名称：

  铜催化氯胺-T与芳基硼酸在室温下反应合成N-芳基磺酰胺

  摘要：

  已经开发了一种铜催化的（杂）芳基硼酸和氯胺-T（或相关化合物）的 Chan-Lam 偶联反应，用于在室温下以中等至良好的收率合成 N-芳基磺酰胺，并具有良好的官能团的耐受性。在此过程中，据信氯胺-T 用作亲电子试剂。

  DOI：

  10.1055/s-0036-1590978

文献信息

• 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。
• Effect of para Substitution on Dissociation of N-Phenylbenzenesulfonamides
  作者：Martin Mansfeld、Patrik Pařík、Miroslav Ludwig

  DOI：10.1135/cccc20041479

  日期：——

  The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C₆H₄SO₂NHC₆H₄-Y-4'. Their purity was checked by elemental analysis. The substituents X and Y include H, CH₃, CH₃O, Cl, Br, CN, and NO₂. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pK_HA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σ_p constants and the Yukawa-Tsuno equation with σ_p^- and σ_p constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO₂ group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.

  替代苯胺和苯磺酰氯的反应已被用于制备49种通式为4-X-C₆H₄SO₂NHC₆H₄-Y-4'的取代N-苯基苯磺酰胺。它们的纯度通过元素分析进行了检查。取代基X和Y包括H、CH₃、CH₃O、Cl、Br、CN和NO₂。所有化合物的解离常数通过在甲醇、乙腈、N,N-二甲基甲酰胺和吡啶中的电位滴定确定。获得的解离常数pKHA与各种取代基常数相关联。发现取代基X和Y对解离的影响最好通过使用带有σp常数的Hammett方程和带有σp-和σp常数的Yukawa-Tsuno方程来描述。这一结果证实了Y取代基与反应中心的直接共轭。在所有使用的溶剂中，使用加性模型解释的可变性超过96%。数据还提供了关于SO₂基团的传输效应的信息。平均解离常数进一步通过潜在变量方法、主成分和共轭偏差分析进行处理。
• Natural Indian Natrolite zeolite-supported Cu nanoparticles: a new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
  作者：Davood Azarifar、Fatemeh Soleimanei

  DOI：10.1039/c3ra47955b

  日期：——

  We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.

  我们在此报告了初级磺酰胺的制备，以及一种高效、易于回收和重用的铜纳米颗粒，支持在天然印度Natrolite沸石上，作为催化剂用于磺酰胺与芳基硼酸在水中进行芳基化反应。催化剂通过粉末XRD、SEM、EDS和FT-IR光谱进行了表征。这种方法的显著优点在于高产率、消除了有机溶剂和简单的后处理程序。催化剂可以轻松从反应混合物中分离，并在不显著降低活性的情况下重复使用。
• Fabrication, characterization and application of nanopolymer supported copper (II) complex as an effective and reusable catalyst for the CN bond cross-coupling reaction of sulfonamides with arylboronic acids in water under aerobic conditions
  作者：Mahmoud Nasrollahzadeh、Akbar Rostami-Vartooni、Ali Ehsani、Majid Moghadam

  DOI：10.1016/j.molcata.2014.02.017

  日期：2014.6

  This paper reports on the synthesis and use of nanopolymer supported copper (II) complex, as separable catalysts for N-arylation of sulfonamides with arylboronic acids in water. This method has the advantages of high yields, elimination of homogeneous catalysts, green reaction conditions, simple methodology and easy work up. The catalyst can be recovered and reused several times without significant

  本文报道了纳米聚合物负载的铜（II）配合物的合成和使用，该配合物可作为磺酰胺与芳基硼酸在水中进行N-芳基化反应的可分离催化剂。该方法具有收率高，消除均相催化剂，绿色反应条件，方法简单，后处理容易的优点。催化剂可以回收并重复使用几次，而不会显着降低其催化活性。使用粉末XRD，SEM，EDS和FT-IR光谱对催化剂进行表征。
• Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
  作者：Banlai Ouyang、Yanxia Zheng、Yi Liu、Fei Liu、Juying Yao、Yiyuan Peng

  DOI：10.1016/j.tetlet.2018.09.001

  日期：2018.10

  A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

  本文开发了一种从氯胺盐和芳基硼酸合成N-芳基磺酰胺的绿色实用方法。在5mol％的CuI和2.5当量的存在下，反应容易进行。室温下水中的K 2 CO 3，以中等至良好的产率生成各种N-芳基磺酰胺，并具有良好的官能团耐受性。