Sciencemadness Discussion Board

Kaiser ninhydrin test: what's the point of the cyanide?

Metacelsus - 21-10-2016 at 17:20

The Kaiser ninhydrin test is used to detect primary amines. The test is based on the reaction of ninhydrin to form a purple-colored product. However, the test also requires two other reagents besides ninhydrin: a solution of phenol and ethanol, and a solution of KCN in pyridine. The test procedure goes like this:

1) Put sample in test tube.
2) Add ninhydrin solution, phenol solution, and KCN/pyridine solution.
3) Heat in boiling water bath for 5 minutes.
4) Check for color change.

It seems like ninhydrin alone would be enough to produce the color. What's the point of the other reagents (especially the KCN)?

CuReUS - 21-10-2016 at 19:50

Quote:
In the search for a more stable and soluble reducing agent we observed that potassium cyanide led to the formation of hydrindantin when added to a solution of ninhydrin

http://www.jbc.org/content/200/2/803.full.pdf+html
the reason for the choice of solvents is also given in that paper

Metacelsus - 21-10-2016 at 19:55

Thanks; that paper was very informative.