2-amino-4-bromobenzenesulfonic acid | 38962-63-9

• 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: 2-amino-4-bromobenzenesulfonic acid
• 英文别名: 2-Aminobrombenzol-4-sulfonsaeure
• CAS: 38962-63-9
• 化学式: C₆H₆BrNO₃S
• 分子量: 252.089
• InChiKey: WWXMMFBBVALMEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴苯并噻唑 在 [RuCl(P(C₆H₅)3)2(O(C₆H₄)NCH(C₄H₃N))] 、 bromamine B 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 5.58h， 以94%的产率得到2-amino-4-bromobenzenesulfonic acid
  参考文献：
  名称：

  Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

  摘要：

  Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (K-c) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.06.006

文献信息

• An Aminative Rearrangement of <i>O</i> ‐(Arenesulfonyl)hydroxylamines: Facile Access to <i>ortho</i> ‐Sulfonyl Anilines
  作者：Charlotte Morrill、James E. Gillespie、Robert J. Phipps

  DOI：10.1002/anie.202204025

  日期：2022.8.15

  An aromatic rearrangement of hydroxylamine derivatives that leads directly to ortho-sulfonyl anilines from simple starting materials is reported. This is achieved through formation of a new C−N bond with excellent levels of regiocontrol for the ortho isomer(s), which is proposed to be the result of attractive non-covalent interactions occurring during the C−N bond-forming step.

  据报道，羟胺衍生物的芳族重排可从简单的起始原料直接生成邻磺酰基苯胺。这是通过形成新的 CN 键来实现的，该键对邻位异构体具有出色的区域控制水平，这被认为是在 CN 键形成步骤中发生有吸引力的非共价相互作用的结果。
• Monoazo compounds and method for dyeing or printing fiber materials using the same
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0719840A1

  公开（公告）日：1996-07-03

  A monoazo compound of the formula (I): wherein D represents a phenyl or naphthyl group; A represents a group of the formula: in which R1 represents a methyl group etc., R2 represents a hydroxyl group or an amino group, R3 represents a hydrogen atom, etc.; or A represents a group of the formula: in which W represents an alkylene group, R4 represents a lower alkyl group, R5 represents a hydrogen atom, a halogen atom, etc.;    R6 and R7 represent a hydrogen atom or a straight chain or branched chain alkyl group    R8 and R9 represent a hydrogen atom, an alkyl group, a cycloalkyl group, a phenyl group or a naphthyl group; n is 2, 3 or 4; Y represents -CH=CH2 or -CH2CH2Z in which Z represents a group removable by the action of an alkali; or a salt thereof, is suitable for dyeing or printing materials having a hydroxy group and/or an amide group.

  式 (I) 的单偶氮化合物： 其中 D 代表苯基或萘基； A 代表式中的一个基团 其中 R1 代表甲基等，R2 代表羟基或氨基，R3 代表氢原子等； 或 A 代表式中的一个基团： 其中 W 代表亚烷基，R4 代表低级烷基，R5 代表氢原子、卤素原子等； R6 和 R7 代表氢原子或直链或支链烷基 R8 和 R9 代表氢原子、烷基、环烷基、苯基或萘基； n 是 2、3 或 4； Y 代表 -CH=CH2 或 -CH2CH2Z，其中 Z 代表在碱作用下可去除的基团； 或其盐，适用于具有羟基和/或酰胺基的染色或印花材料。
• Kupferkomplex-Formazanverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0135040B1

  公开（公告）日：1987-06-24
• Kupferkomplex-Formazan-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0374815B1

  公开（公告）日：1994-05-04
• DICYCLIC METAL COMPLEX FORMAZAN DERIVATIVES, PROCESS FOR PRODUCING THE SAME, COMPOSITION CONTAINING THE SAME AND DYEING PROCESS EMPLOYING THE SAME
  申请人：Kyungin Synthetic Corporation

  公开号：EP0777703B1

  公开（公告）日：2003-06-25