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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: reflux on April 28, 2008, 03:53:03 PM

Title: tertiary amine test
Post by: reflux on April 28, 2008, 03:53:03 PM

Does anyone know of a positive test that will tell you whether you have a secondary versus a tertiary amine?  I have ~1mg of a compound which is very difficult to purify and the nmr is hard to interpret due to its complexity.  Also, the IR is not that useful since there are a fair amount of persistant impurities.

I know of the Hindberg test, but that is only a positive test for secondary and teriary amines (the absence of a ppt suggests a tertiary amine).  Same thing with using various stains, etc.

Any helpful suggestions would be greatly appreciated.

Title: Re: tertiary amine test
Post by: sjb on April 28, 2008, 04:05:50 PM

What are your impurities - do you have any idea?

I'm not sure if 1mg would be enough or if the sensors reported are easy to make in their own right, as I can't access the original paper, but how about the concepts at http://www.ncbi.nlm.nih.gov/pubmed/17200935 ?

Title: Re: tertiary amine test
Post by: reflux on April 28, 2008, 04:13:32 PM

Thank you.  I actually have come upon that paper, but again it would be a "negative" result for a tertiary amine.  I will eventually scale this reaction up but it takes me 2 months to make the material and I want to make sure it is my desired product or I will be wasting alot of time!

I'm afraid one of the impurities is a sulfonamide and a secondary amide which is why I can't trust the IR data.

Also I realize know it is the "Hinsberg" test.  Thanks anyway!