Bromopyrogallol red

Last updated
Bromopyrogallol red
Bromopyrogallol red.svg
Names
Preferred IUPAC name
2′,7′-Dibromo-3′,4′,5′,6′-tetrahydroxy-1H-1λ6-spiro[[2,1]benzoxathiole-3,9′-xanthene]-1,1-dione
Other names
  • 3,3′-Dibromosulfongallein
  • Dibromopyrogallolsulfonphthalein
  • Dibromopyrogallolsulfonphthaleine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.036.923 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 240-632-6
PubChem CID
UNII
  • InChI=1S/C19H10Br2O8S/c20-10-5-8-17(15(24)13(10)22)28-18-9(6-11(21)14(23)16(18)25)19(8)7-3-1-2-4-12(7)30(26,27)29-19/h1-6,22-25H
  • Brc5c(O)c(O)c4Oc1c(O)c(O)c(Br)cc1C3(OS(=O)(=O)c2ccccc23)c4c5
Properties
C19H10Br2O8S
Molar mass 558.15 g·mol−1
AppearancePowder, dark brown [2]
Melting point 300 °C (572 °F; 573 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Not a dangerous substance according to Directive 67/548/EEC
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bromopyrogallol red is frequently used in analytical chemistry as a reagent for spectrophometric analysis and as an complexometric indicator.

Contents

Uses, behaviors, and properties

Bromopyrogallol red is commonly used in analytical chemistry as a spectrophotometric reagent and complexometric indicator. When metal ion complexation reactions are carried out in the presence of quaternary ammonium salts, the analytical possibilities with bromopyrogallol red are even greater. Doing this also increases the color contrast and sensitivity of many elements for analysis. [3] In addition, bromopyrogallol red can also be widely used as a metallochromic indicator. [4] Bromopyrogallol red has been used as a complexometric indicator for determination of Bi, Cd, Co, Mg, and Mn.

Bromopyrogallol red is protonized in 1 M H2SO4 solution and changes gradually to its ionized forms in alkaline solution. In its neutral form, bromopyrogallol red is bipolar ion, containing a protonized carbonyl group as well as a dissociated sulfonate group. Through testing at isobestic points, it has been determined that bromopyrogallol red is a stronger acid than Pyrogallol Red. In the presence of ammonia salts, the bathochromic shifts increase. The hydrophilic group on the ammonia salts also change the dissociation of the reagent to be used with bromopyrogallol red to a more acidic region. [3]

Bromopyrogallol red is also a triphenylmethane indictor. An efficient purification can be obtained by chromatographic separation on a polyamide column prewashed with HCl. Purity can then be checked by thin layer chromatography on a microcrystalline cellulose plate using either a system of butanol–acetic acid–water, n-propanol–water, or methanol–water. Another use of Bromopyrogallol red is as an indicator for titrations with Cd (pH 9.3), Mg (pH 10), Mn (pH10), and lanthanides (pH 7). It also commonly used in back-titrations with Co, Cu, Ga, Pb, and Th. It is usually used as a 0.05% solution in 50% ethanol when used as an indicator. [5]

In pharmacy, bromopyrogallol red serves to bind proteins together. It is used in 30–100 μmol/L concentrations. It has been used in the electrophoretic mobility shift assay and p50 and title comp preincubated in assay buffer, pH 7.5 (room temp., 5 min). [6]

Applications and research

Bromopyrogallol red has numerous applications with analytical chemistry, such as spectrophotometric analysis and as a complexometric indicator.

Spectrophotometric determination

By reacting the bromopyrogallol red with niobium(V) in a tartrate medium at pH 6.0, an intense blue coloured 3:1 reagent was formed. The sensitivity and conditional selectivity of bromopyrogallol red was also studied and results show that trace amounts of silver can be detected from the formation of a ternary complex between 1,10-phenanthroline, bromopyrogallol red and silver ion. This is because of the two adjacent phenol groups in the structure of bromopyrogallol red. [7]

Bromopyrogallol red is used as indicating reagent for rare-earth elements. It is chosen under the spectrophotometric determination method and used as indicator because the reagent forms different visible color. Bromopyrogallol red forms blue to violet-blue complexes with yttrium and cerium. It also has shows orange yellow in strong acid solution, claret red in nearly neutral solution and blue in alkaline solution. [8]

Increased cell efficiency

By forming complex ion of bromopyrogallol red and iron(II) compounds, the efficiency of cell can be increased. The lowest transition in the bromopyrogallol have a MLCT character, which greatly increase the electron sensitivity in Iron (II) and thus the complexation of bromopyrogallol ligand with iron(II) bisoxalato moiety was determined to increase the cell efficiency to a higher level. [9]

Hydrogen donor substrate for peroxidase

Bromopyrogallol red is designed to be a hydrogen donor for peroxidase. Instead of an indicator, bromopyrogallol red is now used as a catalyst, and its reaction rate depends upon enzyme and substrate concentrations. With the HRP-H2O2-BPR catalytic system, the bromopyrogallol red is determined to be an efficient reagent and quantitation of HRP can be performed. It will increase the reaction rate of H2O2 and glucose. [10]

Characterization

Bromopyrogallol red is a green to dark brown crystalline powder. It produces a spectrum in dimethyl sulfoxide with an absorption maxima at 412 and 523 nm. When used with an ethanol solvent, the spectrum ranges from 400 to 540 nm; in H2O it is 360–530 nm, and in 1,4-dioxane and water with a ratio of 4:2, gives an absorption maxima at 470 nm. It is soluble in water and can be stored at 4 °C. [2] [11]

Safety

As a complexometric indicator for determination of : Bi, Cd, Co, Mg, Mn and rare earths, Bromopyrogallol red is not classified as harmful by ingestion. Direct contact with eye may cause tearing or conjunctive redness. It will also cause skin irritation; the entry of bromopyrogallol red into the blood stream may produce systemic injury. The material should also avoid contamination with oxidizing agents like nitrates, oxidizing acids, chlorine bleaches, pool chlorine etc.

See also

Related Research Articles

<span class="mw-page-title-main">Titration</span> Laboratory method for determining the concentration of an analyte

Titration is a common laboratory method of quantitative chemical analysis to determine the concentration of an identified analyte. A reagent, termed the titrant or titrator, is prepared as a standard solution of known concentration and volume. The titrant reacts with a solution of analyte to determine the analyte's concentration. The volume of titrant that reacted with the analyte is termed the titration volume.

<span class="mw-page-title-main">Electrospray ionization</span> Technique used in mass spectroscopy

Electrospray ionization (ESI) is a technique used in mass spectrometry to produce ions using an electrospray in which a high voltage is applied to a liquid to create an aerosol. It is especially useful in producing ions from macromolecules because it overcomes the propensity of these molecules to fragment when ionized. ESI is different from other ionization processes since it may produce multiple-charged ions, effectively extending the mass range of the analyser to accommodate the kDa-MDa orders of magnitude observed in proteins and their associated polypeptide fragments.

<span class="mw-page-title-main">Cerium(IV) sulfate</span> Chemical compound

Cerium(IV) sulfate, also called ceric sulfate, is an inorganic compound. It exists as the anhydrous salt Ce(SO4)2 as well as a few hydrated forms: Ce(SO4)2(H2O)x, with x equal to 4, 8, or 12. These salts are yellow to yellow/orange solids that are moderately soluble in water and dilute acids. Its neutral solutions slowly decompose, depositing the light yellow oxide CeO2. Solutions of ceric sulfate have a strong yellow color. The tetrahydrate loses water when heated to 180-200 °C.

<span class="mw-page-title-main">Bisulfide</span> Inorganic anion containing one sulfur and one hydrogen atoms

Bisulfide is an inorganic anion with the chemical formula HS−. It contributes no color to bisulfide salts, and its salts may have a distinctive putrid smell. It is a strong base. Bisulfide solutions are corrosive and attack the skin.

<span class="mw-page-title-main">Eriochrome Black T</span> Chemical compound

Eriochrome Black T is a complexometric indicator that is used in complexometric titrations, e.g. in the water hardness determination process. It is an azo dye. Eriochrome is a trademark of Huntsman Petrochemical, LLC.

<span class="mw-page-title-main">Murexide</span> Chemical compound

Murexide (NH4C8H4N5O6, or C8H5N5O6·NH3), also called ammonium purpurate or MX, is the ammonium salt of purpuric acid. It is a purple solid that is soluble in water. The compound was once used as an indicator reagent. Aqueous solutions are yellow at low pH, reddish-purple in weakly acidic solutions, and blue-purple in alkaline solutions.

<span class="mw-page-title-main">Silver chromate</span> Chemical compound

Silver chromate is an inorganic compound with formula Ag2CrO4 which appears as distinctively coloured brown-red crystals. The compound is insoluble and its precipitation is indicative of the reaction between soluble chromate and silver precursor salts (commonly potassium/sodium chromate with silver nitrate). This reaction is important for two uses in the laboratory: in analytical chemistry it constitutes the basis for the Mohr method of argentometry, whereas in neuroscience it is used in the Golgi method of staining neurons for microscopy.

<span class="mw-page-title-main">Rosocyanine</span> Chemical compound

Rosocyanine and rubrocurcumin are two red colored materials, which are formed by the reaction between curcumin and borates.

<span class="mw-page-title-main">Molybdenum blue</span> Pigment

Molybdenum blue is a term applied to:

The Charlot equation, named after Gaston Charlot, is used in analytical chemistry to relate the hydrogen ion concentration, and therefore the pH, with the formal analytical concentration of an acid and its conjugate base. It can be used for computing the pH of buffer solutions when the approximations of the Henderson–Hasselbalch equation break down. The Henderson–Hasselbalch equation assumes that the autoionization of water is negligible and that the dissociation or hydrolysis of the acid and the base in solution are negligible.

<span class="mw-page-title-main">Wine color</span> Wine characteristic

The color of wine is one of the most easily recognizable characteristics of wines. Color is also an element in wine tasting since heavy wines generally have a deeper color. The accessory traditionally used to judge the wine color was the tastevin, a shallow cup allowing one to see the color of the liquid in the dim light of a cellar. The color is an element in the classification of wines.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

The Walden reductor is a reduction column filled with metallic silver which can be used to reduce a metal ion in aqueous solution to a lower oxidation state. It can be used e.g. to reduce UO22+ to U4+. The method is named after George H. Walden, who developed it jointly with a Ph.D. student, Sylvan M. Edmonds, at Columbia University.

Cerimetry or cerimetric titration, also known as cerate oximetry, is a method of volumetric chemical analysis developed by Ion Atanasiu. It is a redox titration in which an iron(II)–1,10-phenanthroline complex (ferroin) color change indicates the end point. Ferroin can be reversibly discolored in its oxidized form upon titration with a Ce4+ solution. The use of cerium(IV) salts as reagents for volumetric analysis was first proposed in the middle of 19th century, but systematic studies did not start until about 70 years later. Standard solutions can be prepared from different Ce4+ salts, but often cerium sulfate is chosen.

<span class="mw-page-title-main">Malvidin glucoside-ethyl-catechin</span> Chemical compound

Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.

Jennifer S. Brodbelt is an American chemist known for her research using mass spectrometry to characterize organic compounds, especially biopolymers and proteins.

Hobart Hurd Willard was an analytical chemist and inorganic chemist who spent most of his career at the University of Michigan. He was known for his teaching skill and his authorship of widely used textbooks. His research interests were wide-ranging and involved the characterization of perchloric acid and periodic acid salts.

<span class="mw-page-title-main">Tetraketopiperazine</span> Chemical compound

Tetraketopiperazine is a chemical compound with a molecule containing a six member heterocyclic ring with two nitrogen atoms. Each carbon is doubly bonded to oxygen.

<span class="mw-page-title-main">Calconcarboxylic acid</span> Chemical compound

Calconcarboxylic acid is an azo dye that is used as an indicator for complexometric titrations of calcium with ethylenediaminetetraacetic acid (EDTA) in the presence of magnesium. Structurally, it is similar to eriochrome blue black R, which is obtained from calconcarboxylic acid by decarboxylation and reaction with sodium hydroxide.

<span class="mw-page-title-main">Dithiofluorescein</span> Chemical compound

Dithiofluorescein is a complexometric indicator used in analytical chemistry. It changes from blue to colorless when it binds to mercury(2+) ions. It thus can indicate the endpoint in the titration of thiols using o-hydroxymercuribenzoic acid or its sodium salt. The reagent can be immobilized t in a polymer on a fiber optic, which might allow development of a detector for sulfide ions in a flow cell. Unlike fluorescein and other related fluoran dyes that have oxygen substituents on the benzene rings, dithiofluorescein, which has sulfur substituents, is not fluorescent.

References

  1. ↑ "spiro(3h-2,1-benzoxathiole-3,9'-(9h)xanthene)-3',4',5',6'-tetrol, 2',7'-dibromo-, 1,1-dioxide". ChemSpider. Retrieved 12 April 2013.
  2. 1 2 "Bromopyrogallol Red". Chemical Book. Retrieved 15 March 2013.
  3. 1 2 Wyganowski, C. (1984). "Effect of quaternary ammonium salts on spectrophotometric characteristic of pyrogallol red and bromopyrogallol red". Microchemical Journal. 29 (3): 318–325. doi:10.1016/0026-265X(84)90112-7.
  4. ↑ "Bromopyrogallol Red" (PDF). SCBT. Retrieved 15 March 2013.
  5. ↑ Hulanicki, A.; Glab, S.; Ackermann, G. (1983). "Compleximetric indicators: Characteristics and applications" (PDF). Pure and Applied Chemistry. 55 (7): 1137–1730. doi:10.1351/pac198355071137. S2CID   93875968.
  6. ↑ Sharma, Rakesh K.; Chopra, Shilpa; Sharma, Som D.; Pande, Vineet; Ramos, Maria J.; Meguro, Kazuyuki; Inoue, Masami; Otsuka, Masami (2006). "Biological Evaluation, Chelation, and Molecular Modeling Studies of Novel Metal-Chelating Inhibitors of NF-κB-DNA Binding: Structure Activity Relationships". Journal of Medicinal Chemistry. 49 (11): 3595–3601. doi:10.1021/jm050617x. PMID   16759101.
  7. ↑ West, R. (1965). "Spectrophotometric determination of niobium(V) with bromopyrogallol red". Talanta. 12 (7): 681–690. doi:10.1016/0039-9140(65)80093-5.
  8. ↑ Steed, J.; Steed, K. C. (1960). "Spectrophotometric determination of the rare earths yttrium and cerium by bromopyrogallol red". Analytica Chimica Acta. 22 (7): 180–184. doi:10.1016/S0003-2670(00)88264-1.
  9. ↑ Tennakone, P.; Steed, K. C. (1960). "Spectrophotometric determination of the rare earths yttrium and cerium by bromopyrogallol red". Analytica Chimica Acta. 22: 180–184. doi:10.1016/S0003-2670(00)88264-1.
  10. ↑ Shen, Zhong-Xian; Li, Li; Shen, Han-Xi (1999). "Study and analytical application of bromopyrogallol red as a hydrogen donor substrate for peroxidase". Analytica Chimica Acta. 379 (7): 63–68. doi:10.1016/S0003-2670(98)00625-4.
  11. ↑ Andreeva, I. Yu.; Lebedeva, L. I.; Shablina, M. Yu. (1983). J. Gen. Chem. USSR (Engl. Transl.). 53 (12): 2766–2770, 2494–2497.{{cite journal}}: Missing or empty |title= (help)
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.