Cas no 16574-43-9 (Bromopyrogallol red)

Bromopyrogallol red is a synthetic dye and pH-sensitive indicator commonly used in analytical chemistry. It exhibits a distinct color change from yellow to red in the pH range of 4.8 to 6.2, making it valuable for acid-base titrations and spectrophotometric analyses. The compound is particularly useful in complexometric titrations for detecting metal ions, such as aluminum, beryllium, and rare earth elements, due to its selective chelating properties. Its high molar absorptivity ensures sensitivity in trace metal detection. Bromopyrogallol red is also employed in biochemical assays and as a staining agent in microscopy. The dye is stable under standard laboratory conditions and dissolves readily in aqueous and alcoholic solutions.
Bromopyrogallol red structure
Bromopyrogallol red structure
Product Name:Bromopyrogallol red
CAS No:16574-43-9
MF:C19H10Br2O8S
MW:558.150903224945
MDL:MFCD00148865
CID:50454
PubChem ID:87566920
Update Time:2025-06-09

Bromopyrogallol red Chemical and Physical Properties

Names and Identifiers

    • 2',7'-Dibromo-3',4',5',6'-tetrahydroxyspiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide
    • 5,5-Dibromopyrogallolsulfonephthalein
    • alpha-(5-bromo-2,3-dihydroxy-4-oxo-2,5-cyclohexadienylidene)-alpha-(5-bromo-2,3,4-trihydroxyphenyl)toluenesulphonic acid
    • Bromopyrogallol
    • ROUGE DE BROMOPYROGALLOL
    • Bromopyrogallol Red
    • 2',7'-Dibromo-3',4',5',6'-tetrahydroxyspiro[benzo-[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide
    • BromopyrogallolRed,indicatorgrade,pure1GR
    • BromopyrogallolRed,indicatorgrade,pure5GR
    • Dibromopyrogallolsulfonphthaleine
    • 2',7'-dibromo-1,1-dioxospiro[2,1λ6-benzoxathiole-3,9'-xanthene]-3',4',5',6'-tetrol
    • 3,3′-DibroMosulfongal-lein
    • 5',5''-Dibromopyrogallolsulfonephthalein
    • 5′,5″-DibroMopy-rogallolsulfonphthalein
    • Bromopyrogallol Red, indicator grade, pure
    • tert-Butyl hydroperoxide solution
    • 5',5"-Dibromopyrogallolsulfonephthalein
    • Brompyrogallol Red
    • BromopyrogallolRedGr
    • Pyrogallol bromine red
    • 3,3’Dibromosulfongallein
    • Dibromopyrogallolsulfonphthalein
    • BROMOPYROGALLOL RED, INDICATOR GRADE
    • Spiro(3H-2,1-benzoxathiole-3,9'-(9H)xanthene)-3',4',5',6'-tetrol, 2',7'-dibromo-, 1,1-dioxide
    • Spiro[3H-2,1-benzoxathiole-3,9'-[9H]xanthene]-3',4',5',6'-tetrol, 2',7'-dibromo-, 1,1-dioxide
    • C19H10Br2O8S
    • Brompyrogallolrot
    • N
    • CHEMBL3692122
    • 2',7'-dibromo-1,1-dioxospiro[2,1$l^{6-benzoxathiole-3,9'-xanthene]-3',4',5',6'-tetrol
    • NSC 315537
    • NS00025426
    • Spiro[3H-2,9'-xanthene]-3',4',5',6'-tetrol, 2',7'-dibromo-, 1,1-dioxide
    • AI3-63055
    • NSC315537
    • US8987474, Bromopyrogallol
    • B-8944
    • Spiro[3H-2,9'-[9H]xanthene]-3',4',5',6'-tetrol, 2',7'-dibromo-, 1,1-dioxide
    • D89613
    • SCHEMBL2858413
    • DTXSID0066082
    • FT-0623261
    • ?Bromopyrogallol Red
    • AKOS015904106
    • A882374
    • MFCD00148865
    • UNII-A6NS5EJ2GF
    • EINECS 240-632-6
    • A6NS5EJ2GF
    • 2',7'-dibromo-1,1-dioxospiro[2,1lambda6-benzoxathiole-3,9'-xanthene]-3',4',5',6'-tetrol
    • Ethyl-phosphonic acidDiethyl ester
    • BDBM152155
    • NSC-315537
    • ZINC05641946
    • Bromopyrogallol Red, indicator grade, Dye content 70 %
    • Q926954
    • 16574-43-9
    • QFXYYBXMARTXHI-UHFFFAOYSA-N
    • CS-0009905
    • HY-D0010
    • Bromopyrogallol red
    • MDL: MFCD00148865
    • 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
    • InChI Key: QFXYYBXMARTXHI-UHFFFAOYSA-N
    • SMILES: BrC1C(=C(C2=C(C=1)C1(C3C=C(C(=C(C=3O2)O)O)Br)C2C=CC=CC=2S(=O)(=O)O1)O)O

Computed Properties

  • Exact Mass: 555.84600
  • Monoisotopic Mass: 555.846
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 0
  • Complexity: 756
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 52
  • XLogP3: 3.5
  • Topological Polar Surface Area: 142

Experimental Properties

  • Color/Form: Dark red crystalline powder with metallic luster
  • Density: 2.3900
  • Melting Point: 300 oC
  • Boiling Point: 681.206°C at 760 mmHg
  • Flash Point: 365.8±31.5 °C
  • Water Partition Coefficient: Slightly soluble
  • PSA: 141.90000
  • LogP: 5.23130
  • Solubility: Soluble in ethanol, the solution is red, slightly soluble in water, the aqueous solution is orange red in acidic medium, red in neutral medium, and purple in alkaline medium
  • Vapor Pressure: 0.0±2.2 mmHg at 25°C

Bromopyrogallol red Security Information

Bromopyrogallol red Pricemore >>

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Additional information on Bromopyrogallol red

Chemical Profile of Bromopyrogallol Red (CAS No. 16574-43-9)

Bromopyrogallol Red, identified by the Chemical Abstracts Service Number (CAS No.) 16574-43-9, is a significant compound in the field of organic chemistry and has garnered attention for its versatile applications in biochemical research and industrial processes. This heterocyclic compound, characterized by its brominated pyrogallol structure, exhibits unique spectroscopic and chelating properties that make it invaluable in various scientific and technological domains.

The molecular structure of Bromopyrogallol Red consists of a pyrogallol core substituted with bromine atoms, which imparts enhanced reactivity and stability under a range of conditions. This structural feature allows it to participate in diverse chemical interactions, making it a preferred choice for researchers investigating complex molecular systems. The compound’s ability to form stable complexes with metal ions has been particularly explored in coordination chemistry, where it serves as an effective ligand in catalytic and analytical applications.

In recent years, Bromopyrogallol Red has found increasing relevance in the development of biochemical assays and sensors. Its chromophoric properties enable it to be used as a fluorescent probe, facilitating the detection and quantification of specific analytes in biological samples. For instance, studies have demonstrated its utility in the detection of metal ions such as iron(II) and copper(II), where it forms highly luminescent complexes that can be measured using fluorescence spectroscopy. This capability is particularly valuable in environmental monitoring and clinical diagnostics, where rapid and sensitive detection methods are essential.

Moreover, the compound’s role in pharmaceutical research cannot be overstated. Its structural motif is reminiscent of natural products that exhibit biological activity, prompting investigations into its potential pharmacological effects. Preliminary studies have indicated that derivatives of Bromopyrogallol Red may possess antimicrobial and anti-inflammatory properties, although further research is necessary to fully elucidate these mechanisms. The synthesis of novel analogs tailored for specific biological targets remains an active area of investigation, leveraging the compound’s inherent chemical flexibility.

The industrial applications of Bromopyrogallol Red extend beyond research settings. Its stability under various environmental conditions makes it suitable for use as a corrosion inhibitor in metal processing industries. Additionally, its ability to bind with polyvalent cations has been exploited in water treatment processes to remove heavy metals from aqueous systems. These applications highlight the compound’s practical significance beyond academic research, contributing to sustainable industrial practices.

Advances in synthetic methodologies have further expanded the utility of Bromopyrogallol Red. Modern techniques such as transition-metal-catalyzed cross-coupling reactions have enabled the efficient preparation of brominated pyrogallol derivatives with precise structural control. This has opened new avenues for exploring its reactivity and functionalization potential, paving the way for innovative applications in material science and nanotechnology.

The analytical chemistry community has also benefited from the incorporation of Bromopyrogallol Red into sensing platforms. Its selective binding affinity for certain ions allows it to be integrated into electrochemical sensors, enhancing sensitivity and selectivity in real-world samples. Such sensors are critical for monitoring environmental pollutants and biological markers, contributing to advancements in green chemistry initiatives.

As our understanding of molecular interactions deepens, the role of Bromopyrogallol Red continues to evolve. Its multifaceted properties make it a cornerstone compound in interdisciplinary research, bridging gaps between organic chemistry, biochemistry, and materials science. Future investigations are likely to uncover even more novel applications, reinforcing its status as a pivotal chemical entity in modern science.

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