I'm working on the project in which p-toluenesulfonyl chloride (TsCl) is the main material to synthesis the mono-tosyl substituted. The TsCl in my lab is produce in China and has been opened nearly 8 months, I have purify it by recrystallize in Chloroform/Hexane or CCl4 but the results still not good (poor yield of substitution) so I wonder about it's purity, is it was being degraded?
Is there any analytical method to test the purity of TsCl?
Sandeep Chandrashekharappa all the materials used was dried carefully and the reaction flask was full filled with nitrogen during the reaction time. So I think the problem is the purity of TsCl
As mentioned by others, H NMR and/or C NMR of your TsCl would give you a pretty good idea of the purity of your material. You could do GC/MS if you have access to the instrumentation, but I wouldn't recommend LC/MS as the TsCl could potentially degrade during analysis and give you a false reading on impurities. Another approach, measuring the melting point of your material can tell you if the TsCl is clean or not. Even minor impurities can cause a decrease in the melting point of your material.
Lastly, you could just purchase a new bottle of TsCl and see if that improves your yield.
Hope this all helps, and good luck on your project!
I totally agree with William. However, the proton NMR may not differentiate b/w p-Toluenesulfonic chloride and p-Toluenesulfonic acid that's formed by decomposition, but I think the M.P and GC-MS technique might work best for you.
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