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Congo red

Congo red
Skeletal formula of congo red
Space-filling model of the component ions of congo red
Names
IUPAC name
disodium 4-amino-3-[4-[4-(1-amino-4-sulfonato-naphthalen-2-yl)diazenylphenyl]phenyl]diazenyl-naphthalene-1-sulfonate
Identifiers
573-58-0 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL429694 YesY
ChemSpider 10838 YesY
ECHA InfoCard 100.008.509
MeSH Congo+red
PubChem 11313
UNII 3U05FHG59S YesY
Properties
C32H22N6Na2O6S2
Molar mass 696.665
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Congo red is the sodium salt of 3,3′-([1,1′-biphenyl]-4,4′-diyl)bis(4-aminonaphthalene-1-sulfonic acid) (formula: C32H22N6Na2O6S2; molecular weight: 696.66 g/mol). It is a secondary diazo dye. Congo red is water-soluble, yielding a red colloidal solution; its solubility is better in organic solvents such as ethanol.

It has a strong, though apparently noncovalent, affinity to cellulose fibers. However, the use of Congo red in the cellulose industries (cotton textile, wood pulp, and paper) has long been abandoned, primarily because of its toxicity and tendency to run and change color when touched by sweaty fingers.

Congo red was first synthesized in 1883 by Paul Böttiger, who was working then for the Friedrich Bayer Company in Elberfeld, Germany. He was looking for textile dyes that did not require a mordant step. The company was not interested in this bright red color, so he filed the patent under his name and sold it to the AGFA company of Berlin. AGFA marketed the dye under the name "Congo red", a catchy name in Germany at the time of the 1884 Berlin West Africa Conference, an important event in the Colonisation of Africa. The dye was a major commercial success for AGFA. In the following years, for the same reasons, other dyes were marketed using the "Congo" name: Congo rubine, Congo corinth, brilliant Congo, Congo orange, Congo brown, and Congo blue.

Due to a color change from blue to red at pH 3.0–5.2, Congo red can be used as a pH indicator. Since this color change is an approximate inverse of that of litmus, it can be used with litmus paper in a simple parlor trick: add a drop or two of Congo red to both an acid solution and a base solution. Dipping red litmus paper in the red solution will turn it blue, while dipping blue litmus paper in the blue solution will turn it red. This property gives Congo red a metachromatic property as a dye, both in strongly acidic solutions and with strongly acidophilic tissue.


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