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Bromothymol blue (data page)

Bromothymol blue
Bromothymol-blue-2D-skeletal.png
Bromothymol-blue-3D-balls.png
Names
IUPAC name
4,4′-(1,1-Dioxido-3H-2,1-benzoxathiole-3,3-diyl)bis(2-bromo-6-isopropyl-3-methylphenol)
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.884
PubChem CID
UNII
Properties
C27H28Br2O5S
Molar mass 624.38 g·mol−1
Density 1.25 g/cm3
Melting point 202 °C (396 °F; 475 K)
Sparingly soluble in water
Acidity (pKa) 7.0
Hazards
Safety data sheet See: data page
http://www.sciencelab.com/msds.php?msdsId=9927468
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 code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Bromothymol blue (also known as bromothymol sulfone phthalein and BTB) is a pH indicator. It is mostly used in applications that require measuring substances that would have a relatively neutral pH (near 7). A common use is for measuring the presence of carbonic acid in a liquid. It is typically sold in solid form as the sodium salt of the acid indicator.

Bromothymol blue acts as a weak acid in solution. It can thus be in protonated or deprotonated form, appearing yellow or blue, respectively. It is bright aquamarine by itself, and greenish-blue in a neutral solution. The deprotonation of the neutral form results in a highly conjugated structure, accounting for the difference in color. An intermediate of the deprotonation mechanism is responsible for the greenish color in neutral solution.

The protonated form of bromothymol blue has its peak absorption at 692 nm thus transmitting yellow light in acidic solutions, and the deprotonated form has its peak absorption at 602 nm thus transmitting blue light in more basic solutions.

The general carbon skeleton of bromothymol blue is common to many indicators including chlorophenol red, thymol blue, and bromocresol green.

The presence of one moderate electron withdrawing group (bromine atom) and two moderate donating groups (alkyl substituents) are responsible for bromothymol blue's active indication range from a pH of 6.0 to 7.6. While the conjugation is responsible for the length and nature of the color change range, these substituent groups are ultimately responsible for the indicator's active range.

Bromothymol blue is sparingly soluble in oil, but soluble in water, ether, and aqueous solutions of alkalis. It is less soluble in nonpolar solvents such as benzene, toluene, and xylene, and practically insoluble in petroleum ether.

To prepare a solution for use as pH indicator, dissolve 0.10 g in 8.0 cm3 N/50 NaOH and dilute with water to 250 cm3. To prepare a solution for use as indicator in volumetric work, dissolve 0.1 g in 100 cm3 of 50% (v/v) ethanol.


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