| Bromophenol blue | |
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4,4'-(1,1-dioxido-3H-2,1-benzoxathiole-3,3-diyl)bis(2,6-dibromophenol) |
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| Identifiers | |
| CAS number | 115-39-9 |
| PubChem | 8272 |
| ChemSpider | 7973 |
| ChEBI | CHEBI:59424 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C19H10Br4O5S |
| Molar mass | 669.96 g mol−1 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Bromophenol blue (3',3",5',5"-tetrabromophenolsulfonphthalein) is used as an acid-base indicator, a color marker and a dye.
Contents |
| Bromophenol blue (pH indicator) | ||
| below pH 3.0 | above pH 4.6 | |
| 3.0 | ↔ | 4.6 |
As an acid-base indicator its useful range lies between pH 3.0 and 4.6. It changes from yellow at pH 3.0 to purple at pH 4.6; this reaction is reversible. Bromophenol blue is structurally related to phenolphthalein(a popular indicator).
Bromophenol blue is also used as a color marker to monitor the process of agarose gel electrophoresis and polyacrylamide gel electrophoresis. Since bromophenol blue carries a slight negative charge at moderate pH, it will migrate in the same direction as DNA or protein in a gel; the rate at which it migrates varies according to gel density and buffer composition, but in a typical 1% agarose gel in TAE buffer or TBE buffer, bromophenol blue migrates at the same rate as a DNA fragment of approximately 500 base pairs. Xylene cyanol and Orange G may also be used for this purpose.[1]
Bromophenol blue is also used as a dye. At neutral pH, the dye absorbs red light most strongly and transmits blue light. Solutions of the dye therefore are blue. At low pH, the dye absorbs ultraviolet and blue light most strongly and appears yellow in solution. In solution at pH 3.6 (in the middle of the transition range of this pH indicator) obtained by dissolution in water without any pH adjustment, bromophenol blue has a characteristic green red color. This phenomenon is called dichromatic color.[2] Bromophenol blue is the substance with the highest known value of Kreft's dichromaticity index.[3] This means that it has the largest change in color hue, when the thickness or concentration of observed sample increases or decreases.