1,3-Benzothiazole-5-sulfonic acid | 1245707-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1,3-Benzothiazole-5-sulfonic acid
• CAS: 1245707-84-9
• 化学式: C₇H₅NO₃S₂
• 分子量: 215.254
• InChiKey: KXTNXHFLUHHOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-Benzothiazole-5-sulfonic acid 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 6.0h， 以90%的产率得到2-氨基-1,4-苯二磺酸
  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

• MONO AZO DYES
  申请人：Clariant International Ltd.

  公开号：EP1563011A1

  公开（公告）日：2005-08-17
• US4705861A
  申请人：——

  公开号：US4705861A

  公开（公告）日：1987-11-10
• [EN] MONO AZO DYES<br/>[FR] COLORANTS MONOAZOIQUES
  申请人：CLARIANT INT LTD

  公开号：WO2004044057A1

  公开（公告）日：2004-05-27

  The invention relates to novel azo dyestuffs of formula (I), the use of such compounds and/or mixtures for printing recording materials, especially paper or papery substrates, textile fibre materials, plastic films and plastic transparencies by the inkjet printing process and also to the recording materials printed thereby.
• Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids
  作者：R.V. Jagadeesh、P. Karthikeyan、P. Nithya、Y. Sree Sandhya、S. Sudhaker Reddy、P. Pradeep Kumar Reddy、M. Vinod Kumar、K.T. Prabhu Charan、R. Narender、P.R. Bhagat

  DOI：10.1016/j.molcata.2010.06.006

  日期：2010.8

  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.