Bromophenol blue (original) (raw)

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Bromophenol blue

Skeletal formula of bromophenol blue in cyclic form
Ball-and-stick model of the bromophenol blue molecule in cyclic form
Names
Preferred IUPAC name 3,3-Bis(3,5-dibromo-4-hydroxyphenyl)-2,1λ6-benzoxathiole-1,1(3_H_)-dione
Identifiers
CAS Number 115-39-9 checkY34725-61-6 (sodium salt) checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:59424 checkY
ChEMBL ChEMBL2103765 ☒N
ChemSpider 7973 checkY
ECHA InfoCard 100.003.715 Edit this at Wikidata
PubChem CID 8272
UNII 0R2969YC90 checkY
CompTox Dashboard (EPA) DTXSID6041682 Edit this at Wikidata
InChI InChI=1S/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 checkYKey: UDSAIICHUKSCKT-UHFFFAOYSA-N checkYInChI=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/h1-8,24-25HKey: UDSAIICHUKSCKT-UHFFFAOYAE
SMILES Brc1cc(cc(Br)c1O)C3(OS(=O)(=O)c2ccccc23)c4cc(Br)c(O)c(Br)c4
Properties
Chemical formula C19H10Br4O5S
Molar mass 669.96 g·mol−1
Odor odorless
Density 2.2 g/mL[1]
Melting point 273 °C (523 °F; 546 K)
Boiling point 279 °C (534 °F; 552 K)
Acidity (p_K_a) 4.0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Chemical compound

Bromophenol blue (3′,3″,5′,5″-tetrabromophenolsulfonphthalein, BPB),[2] albutest[3] is used as a pH indicator, an electrophoretic color marker, and a dye. It can be prepared by slowly adding excess bromine to a hot solution of phenolsulfonphthalein in glacial acetic acid.[4]

Acid–base indicator

[edit]

Bromophenol blue (pH indicator)
below pH 3.5 above pH 4.6
3.5 ⇌ 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 blue at pH 4.6; this reaction is reversible.[5] Bromophenol blue is structurally related to phenolphthalein (a popular indicator).

Bromophenol is also used as a colour 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 a 1X TAE buffer or TBE buffer, bromophenol blue migrates at the same rate as a DNA fragment of about 300 base pairs, in 2% agarose as 150 bp. Xylene cyanol and orange G may also be used for this purpose.[6]

Bromophenol blue is also used as a dye. At neutral pH, the dye absorbs red light most strongly and transmits blue light. (Its peak absorbance is 590 nm at a basic pH of 12.) 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 colour, where the apparent colour shifts depending on the concentration and/or path length through which the solution is observed. This phenomenon is called dichromatic color.[7] Bromophenol blue is the substance with the highest known value of Kreft's dichromaticity index.[8] This means it has the largest change in colour hue, when the thickness or concentration of observed sample increases or decreases.

  1. ^ "Bromophenol Blue (CAS 115-39-9) Properties". Santa Cruz Biotechnology, Inc. Retrieved 2022-03-17.
  2. ^ Reaxys. Bromophenol blue (115-39-9) Chemical Names and Synonyms.
  3. ^ "Bromphenol Blue - Compound Summary". PubChem Compound. Retrieved 2022-03-17.
  4. ^ "Bromphenol Blue - Use and Manufacturing". PubChem Compound. Retrieved 2022-03-17.
  5. ^ "Product Specification : Bromophenol Blue" (PDF). Sigmaaldrich.com. Retrieved 2022-03-17.
  6. ^ "Agarose gel electrophoresis (basic method)". Methodbook.net. Retrieved 2008-04-07.
  7. ^ Kreft S, Kreft M (2007). "Physicochemical and physiological basis of dichromatic colour". Naturwissenschaften. 94 (11): 935–9. Bibcode:2007NW.....94..935K. doi:10.1007/s00114-007-0272-9. PMID 17534588. S2CID 33069967.
  8. ^ Kreft S, Kreft M. (2009). "Quantification of dichromatism: a characteristic of color in transparent materials". Journal of the Optical Society of America A. 26 (7): 1576–1581. Bibcode:2009JOSAA..26.1576K. doi:10.1364/JOSAA.26.001576. PMID 19568292.