bromophenol blue

• 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: bromophenol blue
• 英文别名: 3',3'',5',5''-tetrabromo-phenolsulfonphthalein；3,3',5,5'-tetrabromophenolsulfophthalein；2-[(3,5-Dibromo-4-hydroxyphenyl)-(3,5-dibromo-4-oxoniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzenesulfonate
• 化学式: C₁₉H₁₀Br₄O₅S
• 分子量: 669.967
• InChiKey: FKNLPHIFYDXHIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bromophenol blue 以 乙醇 为溶剂， 生成 溴酚蓝
  参考文献：
  名称：

  摘要：

  Protolytic equilibria of hydroxyxanthene dyes, Fluorescein and Eosin, as well as of some related compounds, in ethanol were studied by spectrophotometry. Stepwise ionization and tautomeric equilibrium constants were determined.

  DOI：

  10.1023/a:1024752324071
• 作为产物：
  描述：

  溴酚蓝 以 乙醇 为溶剂， 生成 bromophenol blue
  参考文献：
  名称：

  摘要：

  Protolytic equilibria of hydroxyxanthene dyes, Fluorescein and Eosin, as well as of some related compounds, in ethanol were studied by spectrophotometry. Stepwise ionization and tautomeric equilibrium constants were determined.

  DOI：

  10.1023/a:1024752324071

文献信息

• Heteroassociation of the bromine-containing anions of sulfophthaleins in aqueous solution
  作者：S. A. Shapovalov、Ya. S. Kiseleva

  DOI：10.1007/s11172-010-0241-x

  日期：2010.7

  The ability of bromine-containing anions of sulfophthalein dyes, such as bromophenol blue (BPB), bromocresol green (BCG), bromocresol purple (BCP), bromothymol blue (BTB), as well as non-substituted phenol red (PhR), to form heteroassociates in aqueous solution was investigated. Singly and doubly charged anions BPB, BCG, BCP, BTB, and PhR (HAn-, An2-) are capable of forming stable heteroassociates of composition Ct+•HAn- and (Ct+)2•An2- with cationic polymethine dyes (Ct+), such as pinacyanol and quinaldine red. The enthalpies of formation of the dye ions and heteroassociates were calculated by semiempirical methods, and the most probable structure of heteroassociates was determined.

  研究了溴酚蓝（BPB）、溴甲酚绿（BCG）、溴甲酚紫（BCP）、溴百里酚蓝（BTB）以及非取代酚红（PhR）等酞磺染料的含溴阴离子在水溶液中形成异构体的能力。单电荷和双电荷阴离子 BPB、BCG、BCP、BTB 和 PhR（HAn-、An2-）能够与阳离子聚甲胺染料（Ct+）（如蒎烷醇和喹啉红）形成成分为 Ct+-HAn- 和 (Ct+)2-An2- 的稳定异构体。通过半经验方法计算了染料离子和杂合体的形成焓，并确定了杂合体的最可能结构。
• Bromination of phenol red mediated by vanadium(V) peroxo complexes at pH 6.5
  作者：Roxana M. Tótaro、Patricia A. M. Williams、María C. Apella、Miguel A. Blesa、Enrique J. Baran

  DOI：10.1039/b005733i

  日期：——

  The kinetics of bromination of phenol red (HPhR) to yield bromophenol blue (BrPhB) was studied at pH 6.5, in the presence of peroxovanadium(V) species generated by acid decomposition of [VO(O2)2(NH3)]− and of [OVO(O2)2}2]4−. In the concentration ranges 10−6–10−7 (HPhR), (1.5–8.0) × 10−4 (vanadium complexes) and 0.004–0.12 mol dm−3 (bromide), the rate law is R = k[V]T [Br−][HS], where HS is the substrate undergoing bromination in the rate determining step, with k = 2.49 × 105 dm6 mol−2 s−1. Acid treatment of the precursor complexes yields a mixture of [VO(O2)L]n complexes, with L = H2O, [VO(O2)(H2O)]+, or O22−, [VO(O2)2]−. Alkalinization leads to active species that react with bromide to yield a brominated vanadium complex (e.g. [VO(O2)Br]), which is postulated to be the active bromination agent. Kinetic data rule out the mediation of hypobromous acid. The results support the idea that five-co-ordinated vanadium species are required in the bromination reaction.

  在pH 6.5条件下，研究了苯酚红（HPhR）溴化生成溴酚蓝（BrPhB）的动力学，其中存在由[VO(O2)2(NH3)]−和[OVO(O2)2}2]4−的酸分解产生的过氧化钒（V）物种。在浓度范围10−6–10−7（HPhR）、（1.5–8.0）×10−4（钒络合物）和0.004–0.12 mol dm−3（溴化物）下，速率定律为R = k[V]T [Br−][HS]，其中HS是决定速率步骤中发生溴化的底物，k = 2.49 × 105 dm6 mol−2 s−1。对前体络合物进行酸处理可得到[VO(O2)L]n络合物的混合物，其中L = H2O、[VO(O2)( )]+或O22−、[VO(O2)2]−。碱化可产生活性物种，与溴化物反应生成溴化钒络合物（如[VO(O2)Br]），该络合物被认为是活性溴化剂。动力学
• Regiospecific Oxyhalogenation of Aromatics Over SBA-15-Supported Nanoparticle Group IV–VI Metal Oxides
  作者：L. Saikia、M. Rajesh、D. Srinivas、P. Ratnasamy

  DOI：10.1007/s10562-010-0350-z

  日期：2010.7

  TiOx, VOx, MoOx and WOx supported on SBA-15 exhibit efficient catalytic activity for oxyhalogenation of aromatics with the H2O2-halide ion system. Unlike the hitherto known solid catalysts, these reusable catalysts yield the para-halogenated product with 100% selectivity at 298 K and moderate acidic pH (3-5). The catalytic activity was enhanced by five orders of magnitude when supported on SBA-15.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Mn: MVol.D3, 16.1.37.2, page 244 - 255
  作者：

  DOI：——

  日期：——
• Polymer-anchored peroxo compounds of molybdenum and tungsten as efficient and versatile catalysts for mild oxidative bromination
  作者：Jeena Jyoti Boruah、Siva Prasad Das、Rupam Borah、Sandhya Rani Gogoi、Nashreen S. Islam

  DOI：10.1016/j.poly.2012.09.036

  日期：2013.3

  A polymer supported perozomolybdate(VI) compound of the type [MoO2(O-2)(CN)(2)]-PAN [PAN = poly(acrylonitrile)] (PANMo) was obtained by reacting H2MoO4 with 30% H2O2 and the macromolecular ligand, PAN at near neutral pH. The macrocomplex has been characterized by elemental analysis (CHN and EDX analysis), spectral (IR, UV-Vis and C-13 NMR, Mo-95 NMR), thermal (TGA-DTG) as well as SEM studies. The catalytic activity of PANMo and its previously reported tungsten containing analog PANW, in oxidative bromination of organic substrates has been explored. The supported complexes could serve as efficient heterogeneous catalysts for the oxidative bromination of a variety of structurally diverse aromatic compounds, with H2O2 as terminal oxidant, to afford bromo organics in impressive yields under environmentally clean conditions. The catalysts afforded regeneration and could be reused for a minimum of six reaction cycles. (C) 2012 Elsevier Ltd. All rights reserved.