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115-39-9 Usage

Chemical Properties

Bromophenol Blue is pink or red powder, soluble in ethanol, benzene, ether and other organic solvents, slightly soluble in water, the aqueous solution is yellow, and blue-purple in alkaline solution. It is mainly used as an acid-base indicator, the pH discoloration range is 3.0 to 4.6, and the color changes from yellow to green to blue-violet.

Uses

Different sources of media describe the Uses of 115-39-9 differently. You can refer to the following data:
1. Bromophenol Blue is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.
2. Bromophenol blue is used as a tracking dye in electrophoresis, as a color marker in gel electrophoresis and polyacrylamide gel electrophoresis. As a biological stain, it plays an important role to stain proteins and nucleic acids. It acts an intermediate and an acid-base indicator in the pH range 3.0 to 4.6.

Preparation

Synthesis of bromophenol blue: Dissolve phenol red in glacial acetic acid, add a solution of bromine in glacial acetic acid with stirring, pour into 60°C hot water after stirring for a few minutes, cool to room temperature, and place overnight. Filter, wash the filter cake with glacial acetic acid and benzene in turn, and air dry to obtain bromophenol blue.

Definition

ChEBI: Bromophenol blue is 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye. It has a role as a two-colour indicator, an acid-base indicator and a dye. It is a sultone, an arenesulfonate ester, a 2,1-benzoxathiole, a member of phenols and an organobromine compound.

Biotechnological Applications

Bromophenol blue is present as a sulfonated hydroxyquinone in acidic aqueous solutions. It is also known as tetrabromophenolsulfonphthalein. Bromophenol Blue is a pH indicator and a dye appears a strong blue color. It has a slightly negative charge and will migrate in the same direction as DNA, allowing the user to monitor the progress of molecules moving through the gel. The rate of migration varies with gel composition.Bromophenol Blue is used as a tracking dye in DNA, RNA (agarose) and protein (polyacrylamide) gel electrophoresis. It has been used in the preparation of protein samples for western blotting analysis. Bromophenol blue migrates at approximately the same rate as 300-500bp DNA in agarose gel and at the buffer front in protein polyacrylamide gels.It has also been known for its use as a vital stain to probe the blood-brain barrier.

Purification Methods

Crystallise the dye from *C6H6 or Me2CO/AcOH, and dry it in air. It is an indicator: at pH 3.0 it is yellow and it is purple at pH 4.6. [Beilstein 19/3 V 458.]

Check Digit Verification of cas no

The CAS Registry Mumber 115-39-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 115-39:
(5*1)+(4*1)+(3*5)+(2*3)+(1*9)=39
39 % 10 = 9
So 115-39-9 is a valid CAS Registry Number.
InChI:InChI=1/C19H10Br4O5S/c20-12-5-9(6-13(21)17(12)24)19(10-7-14(22)18(25)15(23)8-10)11-3-1-2-4-16(11)29(26,27)28-19/h1-8,24-25H

115-39-9 Well-known Company Product Price

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  • CAS number
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  • Detail
  • Alfa Aesar

  • (32641)  Bromophenol Blue, ACS   

  • 115-39-9

  • 1g

  • 51.0CNY

  • Detail
  • Alfa Aesar

  • (32641)  Bromophenol Blue, ACS   

  • 115-39-9

  • 5g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (32641)  Bromophenol Blue, ACS   

  • 115-39-9

  • 25g

  • 708.0CNY

  • Detail
  • Alfa Aesar

  • (A18469)  Bromophenol Blue   

  • 115-39-9

  • 10g

  • 338.0CNY

  • Detail
  • Alfa Aesar

  • (A18469)  Bromophenol Blue   

  • 115-39-9

  • 50g

  • 531.0CNY

  • Detail
  • Fluka

  • (18046)  BromophenolBluesolution  ~1% in DMF, indicator

  • 115-39-9

  • 18046-50ML

  • 1,302.21CNY

  • Detail
  • Fluka

  • (32712)  BromophenolBlue  Reag. Ph. Eur., indicator

  • 115-39-9

  • 32712-5G

  • 501.93CNY

  • Detail
  • Fluka

  • (32712)  BromophenolBlue  Reag. Ph. Eur., indicator

  • 115-39-9

  • 32712-25G

  • 1,421.55CNY

  • Detail
  • Sigma-Aldrich

  • (B0126)  BromophenolBlue  

  • 115-39-9

  • B0126-25G

  • 394.29CNY

  • Detail
  • Sigma-Aldrich

  • (114391)  BromophenolBlue  ACS reagent

  • 115-39-9

  • 114391-5G

  • 232.83CNY

  • Detail
  • Sigma-Aldrich

  • (114391)  BromophenolBlue  ACS reagent

  • 115-39-9

  • 114391-25G

  • 755.82CNY

  • Detail

115-39-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name bromophenol blue

1.2 Other means of identification

Product number -
Other names 3',3'',5',5''-Tetrabromophenolsulfonephthalein

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:115-39-9 SDS

115-39-9Synthetic route

phenol red
143-74-8

phenol red

bromophenol blue
115-39-9

bromophenol blue

Conditions
ConditionsYield
With perchloric acid; dihydrogen peroxide; C14H9BrN2O4V(1-); potassium bromide In water at 0 - 24℃; for 0.666667h; Catalytic behavior; Reagent/catalyst; Temperature;89%
With C12H8N2*C13H11N3O3(2-)*OV(2+); dihydrogen peroxide; potassium bromide In water Kinetics; Concentration; aq. phosphate buffer;
With [V(1,3-benzenedicarboxyliate)(2,6-pyridinedicarboxylate)(H2O)2]; potassium bromide In water; N,N-dimethyl-formamide at 30℃; pH=5.8; Kinetics; Reagent/catalyst;
Conditions
ConditionsYield
In dichloromethane Equilibrium constant;
2-[Bis-(3,5-dibromo-4-hydroxy-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

2-[Bis-(3,5-dibromo-4-hydroxy-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

A

triethylamine
121-44-8

triethylamine

B

bromophenol blue
115-39-9

bromophenol blue

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant; other solvents;
C19H10Br4O5S*2C17H23NO3

C19H10Br4O5S*2C17H23NO3

A

bromophenol blue
115-39-9

bromophenol blue

atropine
51-55-8

atropine

Conditions
ConditionsYield
In dichloromethane at 17℃; Equilibrium constant; Thermodynamic data; other temperatures; ΔH0, ΔS0, ΔG0;
phenol red
143-74-8

phenol red

A

bromocresol red
2800-80-8

bromocresol red

B

bromophenol blue
115-39-9

bromophenol blue

Conditions
ConditionsYield
With dihydrogen peroxide; sodium bromide In phosphate buffer at 30℃; for 5.83333h; pH=0.5 - 4.5; Bromination;
phenolsulfonphthalein

phenolsulfonphthalein

bromophenol blue
115-39-9

bromophenol blue

Conditions
ConditionsYield
With ethanol; bromine
With bromine; acetic acid
bromophenol blue

bromophenol blue

bromophenol blue
115-39-9

bromophenol blue

Conditions
ConditionsYield
In ethanol Equilibrium constant;
triethylamine
121-44-8

triethylamine

acetyl chloride
75-36-5

acetyl chloride

bromophenol blue
115-39-9

bromophenol blue

C21H12Br4O6S*C6H15N

C21H12Br4O6S*C6H15N

Conditions
ConditionsYield
In dichloromethane at 20℃; for 6h; Inert atmosphere;82%
benzyl chloroformate
501-53-1

benzyl chloroformate

bromophenol blue
115-39-9

bromophenol blue

2-benzyloxycarbonylaminoethylamine
72080-83-2

2-benzyloxycarbonylaminoethylamine

Conditions
ConditionsYield
With sodium hydroxide; ethylenediamine In methanol; water54%
4-carboxyphenylboronic acid
14047-29-1

4-carboxyphenylboronic acid

bromophenol blue
115-39-9

bromophenol blue

3'-bromo-5'-[3-(3,5-dibromo-4-hydroxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ6-benzo[c][1,2]oxathiol-3-yl]-2'-hydroxy-biphenyl-4-carboxylic acid
591771-44-7

3'-bromo-5'-[3-(3,5-dibromo-4-hydroxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ6-benzo[c][1,2]oxathiol-3-yl]-2'-hydroxy-biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate; cross-linked resin-captured palladium In water at 120℃; for 0.166667h; Suzuki coupling reaction; microwave irradiation;41%
With potassium phosphate; tetrabutylammomium bromide; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 18h; Suzuki coupling;33%
With potassium phosphate; palladium diacetate In N,N-dimethyl-formamide Suzuki cross-coupling;33%
Conditions
ConditionsYield
In dichloromethane Equilibrium constant; Thermodynamic data; ΔH0, ΔS0, ΔG0;
bromophenol blue
115-39-9

bromophenol blue

A

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

B

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

Conditions
ConditionsYield
at 16℃; Equilibrium constant; ΔH, ΔS, ΔG (excit.), variation of temperature;
triethylamine
121-44-8

triethylamine

bromophenol blue
115-39-9

bromophenol blue

2-[Bis-(3,5-dibromo-4-hydroxy-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

2-[Bis-(3,5-dibromo-4-hydroxy-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant; other solvents;
bromophenol blue
115-39-9

bromophenol blue

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

C19H10Br4O5S*C14H18N4O3
74152-31-1

C19H10Br4O5S*C14H18N4O3

Conditions
ConditionsYield
In ethyl acetate Ambient temperature;0.15 g
bromophenol blue
115-39-9

bromophenol blue

homatropine
114173-36-3

homatropine

A

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

B

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

2-[(3,5-Dibromo-4-hydroxy-phenyl)-(3,5-dibromo-4-oxo-cyclohexa-2,5-dienylidene)-methyl]-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions
ConditionsYield
at 15℃; Kinetics; Equilibrium constant; ΔH, ΔS, ΔG (excit.), variation of temperature;
bromophenol blue
115-39-9

bromophenol blue

bromophenol blue

bromophenol blue

Conditions
ConditionsYield
In ethanol Equilibrium constant;
bromophenol blue
115-39-9

bromophenol blue

[5-({3'-bromo-5'-[3-(3,5-dibromo-4-hydroxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ6-benzo[c][1,2]oxathiol-3-yl]-2'-hydroxy-biphenyl-4-carbonyl}-amino)-pentyl]-carbamic acid tert-butyl ester
694464-87-4

[5-({3'-bromo-5'-[3-(3,5-dibromo-4-hydroxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ6-benzo[c][1,2]oxathiol-3-yl]-2'-hydroxy-biphenyl-4-carbonyl}-amino)-pentyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 33 percent / K3PO4; (n-Bu)4NBr / Pd(OAc)2 / dimethylformamide / 18 h / 110 °C
2: 85 percent / tetramethylfluoroformamidinium hexafluorophosphate; Et3N / dimethylformamide / 18 h
View Scheme

115-39-9Related news

Accurate investigation to determine the best conditions for using NiTiO3 for Bromophenol Blue (cas 115-39-9) degradation in the environment under UV–vis light based on concentration reduction and to compare it with TiO208/26/2019

In this study, bromophenol blue was degraded by NiTiO3 nanoparticles under UV and Visible light irradiation. Due to the toxicity and harmful effects of the bromophenol blue compound in ground and surface water, its photocatalytic decomposition is of utmost importance. NiTiO3 photocatalyst was sy...detailed

Sunlight induced catalytic degradation of Bromophenol Blue (cas 115-39-9) and antibacterial performance of graphene nanoplatelets/polypyrrole nanocomposites08/25/2019

Graphene-polymer nanocomposites are innovative materials that have attracted much attention due to their novel features. Herein, we report photocatalytic and antibacterial properties of GNP-PPy nanocomposites. The formation of nanocomposites was confirmed by various characterization techniques. ...detailed

Preferential solvation Bromophenol Blue (cas 115-39-9) in water-alcohol binary mixture08/22/2019

In this study, the perichromic behavior of bromophenol blue (BPB) in various binary solvent mixtures was investigated. The binary mixtures considered were comprised of water and methanol (MeOH), ethanol (EtOH), n-propanol (n-PrOH), isopropanol (iso-PrOH) or t-butanol (t-BuOH). The investigation ...detailed

115-39-9Relevant academic research and scientific papers

Dinuclear vanadium complexes with rigid phenylpolycarboxylate ligands: Synthesis, structure, and catalytic bromination reaction with potential detection of hydrogen peroxide

Zhang, Rui,Zhang, Xiao-Xi,Bai, Feng-Ying,Chen, Chen,Guan, Qing-Lin,Hou, Ya-Nan,Wang, Xuan,Xing, Yong-Heng

, p. 1613 - 1628 (2014)

Vanadium complexes (VO)2(2,2′-bipy)2(bta) (H2O)2 (1) and (VO)2(1,10-phen) 2(bta)(H2O)2 (2) (H4bta = 1,2,4,5-benzenetetracarboxylic acid, 2,2′-bipy = 2,2-bipyridine and 1,10-phen = 1,10-phenanthroline) have been synthesized by the reaction of V 2(SO4)3, H4bta, 2,2′-bipy (for 1) and 1,10-phen (for 2) by hydrothermal methods. The complexes were characterized by elemental analysis, IR, UV-vis, thermogravimetric analyses, and single-crystal X-ray diffraction. Structural analyses indicate that 1 and 2 are both VO-bta-N-heterocycle system complexes. The central vanadium is coordinated by N2O4 donors to form a distorted octahedral geometry. The complexes exhibit catalytic bromination activity in a single-pot reaction with conversion of phenol red to bromophenol blue in a mixed solution of H 2O-DMF at 30 ± 0.5°C with pH 5.8, indicating that they can be considered as a functional model of vanadium-dependent haloperoxidases. The practical application of H2O2 detection has also been studied. 2014

Synthesis, structure, and catalytic bromination of supramolecular oxovanadium complexes containing oxalate

Chen, Chen,Bai, Feng-Ying,Zhang, Rui,Song, Ge,Shan, Hui,Xing, Na,Xing, Yong-Heng

, p. 671 - 688 (2013)

Three supramolecular complexes, [VO(phen)(C2O 4)(H2O)]·CH3OH (1) [(VO) 2(u2-C2O4)(C2O 4)2(H2O)2]·L·H 2O (2), and [(4,4′-bipyH2)0.5] +[VO2(2,6-dipic)]-·2H2O (3) (phen = 1,10-phenanthroline 4,4′-bipy = 4,4′-bipyridine, 2,6-dipic = 2,6-pyridinedicarboxylic, L = 1,4-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl) benzene), have been prepared and characterized by elemental analysis, IR, and UV-vis spectroscopy and single-crystal diffraction analysis. Structural analysis shows that the three complexes all contain carboxylate and V=O moiety; vanadium of 1 and 2 are six coordinate with distorted octahedral geometry with N 2O4 and O6 donor sets, respectively, while 3 is five coordinate with distorted trigonal bipyramidal geometry with a NO 4 donor set. The complexes exhibit catalytic bromination activity in the single-pot reaction for the conversion of phenol red to bromophenol blue in H2O-DMF at 30 ± 0.5 C with pH 5.8, indicating that they can be considered as functional model vanadium-dependent haloperoxidases. In addition, electrochemical behaviors are also studied.

Development of a multifunctional biomimicking l-cysteine based oxovanadium(IV) complex: Synthesis, DFT calculations, bromo-peroxidation and nuclease actIVity

Saha, Urmila,Mukherjea, Kalyan K.

, p. 94462 - 94473 (2015)

An oxovanadium complex [VO(sal-l-cys)(phen)] (sal-l-cys = Schiff base derived from salicylaldehyde and l-cysteine; phen = 1,10-phenanthroline) has been synthesized and characterized by spectroscopic studies (IR, UV-vis, ESI-MS and EPR studies). The structure of the complex has been optimized by density functional theory (DFT) calculations. Time-dependent DFT (B3LYP) calculations were used to establish and understand the nature of the electronic transitions observed in UV-vis spectra of the ligand and the complex. The multifunctionality of this oxovanadium complex has been exhibited by the application of it as a catalyst in peroxidative bromination of phenol red to demonstrate vanadium dependent bromoperoxidase activity, whereas nuclease activity has been established by DNA cleavage. The interaction of DNA with this structurally characterized oxovanadium complex has been studied by various physicochemical tools like UV-vis, fluorescence, and viscosity measurement studies. The intrinsic binding constant of the complex with DNA has been determined by electronic absorption studies and calculated to be (3.51 ± 0.02) × 104 M-1. The spectroscopic studies and the viscosity measurements indicate that the complex binds CT DNA by an intercalative mode. The ability of the complex to induce DNA cleavage was studied by gel electrophoresis techniques. The complex has been found to promote cleavage of pUC19 plasmid DNA from the super coiled (SC) form I to nicked coiled (NC) relaxed form II.

Ionization and Tautomerism of Hydroxyxanthenes and Some Other Dyes in Ethanol

Mchedlov-Petrosyan

, p. 267 - 274 (2003)

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.

Bromoperoxidase mimic as catalysts for oxidative bromination - Synthesis, structures and properties of the diversified oxidation state of vanadium(iii, iv and v) complexes with pincer N-heterocycle ligands

Chen, Chen,Sun, Qiao,Ren, Dong-Xue,Zhang, Rui,Bai, Feng-Ying,Xing, Yong-Heng,Shi, Zhan

, p. 5561 - 5573 (2013)

Novel oxovanadium complexes (VO)2(bpz*T-O) (1), VO(bpz*eaT)(SCN)2 (2), V2(bpz*eaT) 2(μ2-C2O4)(C2O 4)2 (3), [VO(SO4)(bpz*P)(H 2O)]·H2O (4) and VO(SO4)(bpz*P-Me) (H2O) (5) (bpz*T-O: 4,6-bis(3,5-dimethylpyrazol-1-yl)-1,3,5- triazin-2-olate, bpz*eaT: 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6- diethylamino-1,3,5-triazine, bpz*P: 2,6-bis(5-methyl-pyrazol-3-yl) pyridine, bpz*P-Me: 2,6-bis(1,5-dimethyl-pyrazol-3-yl)pyridine), were synthesized by the reaction of V2(SO4)3- VOSO4-VO(acac)2 and various pincer N-heterocyclic ligands with solution or hydrothermal methods. The structures of all the complexes were characterized by elemental analysis, IR and UV-vis spectroscopy and single-crystal diffraction analysis. Furthermore, thermogravimetric analyses (TG) and quantum chemistry calculations were also performed. Structural analyses reveal that the vanadium atom has a distorted trigonal bipyramidal geometry with a N3O2 donor set in 1; distorted octahedral geometry in 2, 4 and 5 with donor sets of N5O, N3O3 and N3O3, respectively; a distorted pentagonal bipyramidal geometry with a N3O4 donor set in 3. In addition, the five new complexes with abundant intro- and inter-hydrogen bonding interactions exhibited bromination catalytic activity in a single-pot reaction of the conversion of phenol red to bromophenol blue in a mixed solution of H 2O-DMF at a constant temperature of 30 ± 0.5°C with a buffer solution of NaH2PO4-Na2HPO4 (pH = 5.8), indicating that they can be considered as a potential functional model of bromoperoxidase. The Royal Society of Chemistry 2013.

Polyoxidovanadate complexes: synthesis, structures and catalytic oxidative bromination of phenol red

Lin, Xiao-Meng,Feng, Xiao-Dong,Wang, Yang,Xing, Yong-Heng,Sun, Li-Xian,Wei, Si-Yue,Shi, Zhan

, p. 44 - 59 (2017)

By selecting appropriate ligands, two polyoxidovanadate complexes, [Ni(en)2]3[V18O42Cl]·7H2O·2H3O+ (1) and [H2N(CH3)2]3[PV14O42]·2TMP·6H3O+ (2), have been synthesized at different pH values using V2(SO4)3, Ni(CH3COO)2, and H6TTHA (for 1), VO(acac)2 and TPP (for 2) (en?=?C2H8N2, TPP?=?thiamine pyrophosphate, TMP?=?thiamine monophosphate, H6TTHA?=?1,3,5-triazine-2,4,6-triamine hexaacetic acid). The complexes have been characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis (TG), and single crystal X-ray diffraction. The complexes catalyze the oxidation of the organic substrate phenol red in the presence of H2O2 and bromide, and the reaction system is considered as a model for hydrogen peroxide determination. The reaction rate constants (k) for 1 and 2 are calculated as 3.729?×?103 and 4.083?×?103 (mol?L)?2?s?1. The maximum conversion rate of phenol red for 1 is 83.32%, while for 2 is 81.12%.

Experimental and theoretical studies on vanadium bromoperoxidase activity of alkyne arm dioxidovanadium(V) complex: Crystal structure, spectral studies, and DFT calculations

Neelakantan,Balakrishnan, Chithiraivel,Kowsalya,Selvarani

, p. 191 - 199 (2018)

The alkyne arm bearing dioxidovanadium(V) complex was synthesized by the reaction of vanadium sulphate, 1-[2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethanone and propane-1,2-diamine. The synthesized complex was characterized by various spectral techniques and its structure was determined using single-crystal X-ray diffraction analysis. Vanadium centre has square-pyramidal based geometry with an axial oxido ligand and the equatorial positions are occupied by another oxido ligand and phenolato oxygen, imine nitrogen and free amine nitrogen atoms. DFT and TD-DFT calculations were examined to identify the electronic structure, and electronic transitions of the complex observed in the absorption spectra. The percentage of intermolecular interactions in the crystal structure has been evaluated by 3D Hirshfeld surfaces and 2D fingerprint plots. The C–H?π and intermolecular interactions of the complex were examined using Bader's theory of QTAIM by ADF 2017. The dioxidovanadium(V) complex mimics as an efficient vanadium-dependent bromoperoxidase towards the bromination of phenol red in acetonitrile medium at room temperature.

Synthesis, characterization, crystal structure, and reactivity of heterobimetallic dioxovanadium(V) complexes containing multidentate hydrazone ligands

Kurbah, Sunshine D.,Kumar, Arvind,Sanentiba Ozukum,Syiemlieh, Ibanphylla,Lal, Ram A.

, p. 2969 - 2985 (2017)

Two new heterobimetallic complexes of the composition [(VO2)2(μ3-slsch){Na2(μ-H2O)2(H2O)2}]n (1) and [(VO2)2(μ3-npsch){Na2(μ-H2O)2(H2O)2}(DMF)]n (2) were obtained by reaction of the ligand and vanadium pentoxide in a 1:1 molar ratio in methanol in the presence of Na2CO3 (2 equivalents). The complexes obtained were characterized using various spectroscopic studies. The structures of both the complexes were established by single crystal X-ray crystallographic study. We have also explored the catalytic behavior of the complexes in oxidative bromination of phenol red, which is the bio-inspired reaction catalyzed by an enzyme haloperoxidase.

Mimicking vanadium haloperoxidases: Vanadium(iii)-carboxylic acid complexes and their application in H2O2 detection

Feng, Xiao Dong,Zhang, Xiao Xi,Wang, Zhi Nan,Song, Jian,Xing, Yong Heng,Bai, Feng Ying

, p. 1222 - 1229 (2016)

Vanadium(iii) complexes [V(2,6-pdc)2(H2O)2]·2H2O (1) and V(2,6-pdc)(htba)(H2O)2 (2), (2,6-pdc = 2,6-pyridinedicarboxylic acid, htba = 2-acetoxy-4-trifluoromethylbenzoic acid) have been synthesized by the reaction of V2(SO4)3 with 2,6-pdc (for 1) or 2,6-pdc and htba (for 2) under hydrothermal conditions at 120 °C for 36 hours. Because the vanadium(iii) was easily oxidized into higher oxidation states, we included the reducing agent vitamin C to protect the vanadium(iii) center. The complexes were characterized by elemental analysis, IR and UV-vis spectroscopy, and single-crystal X-ray diffraction. Structural analysis revealed that the central metal V atoms in the complexes 1 and 2 were seven-coordinate, forming pentagonal bipyramid geometries. The complexes catalyzed the bromination of the organic substrate phenol red in the presence of H2O2, bromide and buffer. Compared with vanadium complexes having other oxidation states, the vanadium(iii) complexes had better catalytic activity (the maximum reaction rate constant was 2.424 × 102k(mol L-1)-2 s-1). The mimicking vanadium haloperoxidases also overcame some serious disadvantages of natural enzymes. Therefore, the reaction system described herein can be considered as an effective model for hydrogen peroxide determination.

Novel vanadium complexes with rigid carboxylate ligands: Synthesis, structure and catalytic bromine dynamics of phenol red

Wang, Yang,Lin, Xiao-Meng,Bai, Feng-Ying,Sun, Li-Xian

, p. 379 - 386 (2017)

In this work, by selecting appropriate ligands, novel vanadium complexes [VIVO(2,6-pdc)(Phen)]·3H2O (1) and [(VIVO)(C5H5N2O2)2H2O]·2H2O (2) (2,6-pdc = 2,6-pyridinedicarboxylic acid, Phen = 1,10-Phenanthroline monohydrate) were synthesized by the reaction of V2(SO4)3, 2,6-pdc and Phen (for 1), VO(acac)2 and C5H6N2O2 (for 2) via solution or hydrothermal methods. Two complexes were characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis (TG), UV-vis spectroscopy and the single crystal X-ray diffraction. Structural analyses reveal that the vanadium atom has distorted octahedral geometry in 1 and 2 with donor sets of N3O3 and N2O4, respectively. The complexes which catalyze the oxidation of the organic substrate phenol red in the presence of H2O2 and bromide exhibited catalytic bromination activity, and the reaction system is considered as an effective model for hydrogen peroxide determination. The reaction rate constant (k) for complexes 1 and 2 can be calculated as 2.13 × 102 and 2.64 × 102 (mol/L)?2s?1, respectively.

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