Bromocresol green

Bromocresol green
Names
IUPAC name
2,6-Dibromo-4-[7-(3,5-dibromo-4-hydroxy-2-methyl-phenyl)-9,9-dioxo-8-oxa-9λ6-thiabicyclo[4.3.0]nona-1,3,5-trien-7-yl]-3-methyl-phenol
Other names
3,3',5,5'-Tetrabromo-m- cresolsulfonphthalein
Identifiers
Abbreviations BCG
76-60-8 Yes
ChEMBL ChEMBL145704 Yes
ChemSpider 6209 Yes
Jmol-3D images Image
PubChem 6451
Properties
Molecular formula
 C21H14Br4O5S
Molar mass 698.01 g·mol−1
Appearance beige to brown powder
Odor odorless
Melting point 225 °C (437 °F; 498 K) decomposes[1]
Acidity (pKa) 4.90[2]
UV-vis (λmax) 423 nm[1]
Hazards
R-phrases R36/38
S-phrases S24/25, S28, S37, S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
Infobox references

Bromocresol green (BCG) is a dye of the triphenylmethane family (triarylmethane dyes). It is used as a pH indicator in applications such as growth mediums for microorganisms and titrations.

Bromocresol green (pH indicator)
below pH 3.8 above pH 5.4
3.8 ⇌ 5.4

Properties

In aqueous solution, Bromocresol green will ionize to give the monoanionic form (yellow), that further deprotonates at higher pH to give the dianionic form (blue),[3] which is stabilized by resonance:

The Dissociation constant (pKa) of this reaction is 4.8.[4]

The acid and basic forms of this dye have an isosbestic point in their spectra, around 515 nm.

An ethanol solution (0.04 wt.%) of bromocresol green has been proposed for TLC staining and is suitable for visualisation of the compounds with functional groups whose pKa is below 5.0 (carboxylic acids, sulfonic acids, etc.). These appear as yellow spots on a light or dark blue background; no heating is necessary. Bromophenol blue solution can be used for the same purpose.

The compound is synthesized by bromination of cresol purple (m-cresolsulfonphthalein).

Gallery

Demonstration of the isosbestic point of bromocresol green at which the different forms have the same absorbance

Uses

It is used as a pH indicator and as a tracking dye for DNA agarose gel electrophoresis. It can be used in its free acid form (light brown solid), or as a sodium salt (dark green solid). It is also an inhibitor of the prostaglandin E2 transport protein.

Safety

Bromocresol green may cause irritation. Avoid skin and eye contact.

References

  1. ↑ 1.0 1.1 "Bromocresol Green". Sigma Aldrich.
  2. ↑ Kolthoff, I.M. Treatise on Analytical Chemistry, New York, Interscience Encyclopedia, Inc., 1959.
  3. ↑ Fred Senese. "Acid-Base Indicators". Frostburg State University Dept. of Chemistry.
  4. ↑ Diamond, D.; Lau, K. T.; Brady, S.; Cleary, J. (2008). "Integration of analytical measurements and wireless communications—Current issues and future strategies". Talanta 75 (3): 606. doi:10.1016/j.talanta.2007.11.022.