pyrrole

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Preparation of something really pure. This compound (a highly substituted dihydroxy pyrrole) was made by me at least tenth time, but since a slight contamination (1-5%) was always present in the final product, it always had a green fluorescence.

Now, finally I found an easy was to purify the product and I was able to make it in a +99,5% purity.

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Crystals of sublimed 2-(trifluoroacetyl)pyrrole.

The raw reaction product what was an off-white crystalline compound with a melting point 50 °C was loaded in a test tube and left there for a few months. For now, these crystals formed at the wall what are perfectly pure 2-(trifluoroacetyl)pyrrole.

If this compound is left on a Petri dish for a day, most of it will sublime away.

5

Yesterday I have made something really new and really pure, a highly substituted pyrrole what crystallized on standing during the night to give these nice round crystals at the bottom of the flask.  

The best pictures from the blog, what are tagged as my portfolio, including these pictures, could be purchased at Society6 as a high quality great looking print: http://society6.com/labphoto now with a free worldwide shipping promotion till October 12, 2014, for every art print.

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These crystals are the first results of a several month long work, they are a quite special substituted pyrrole what could be polymerized quite easily and it will give a conductive polymer.

Even through the crystals have a slight brownish coloration, they are perfectly pure, according to the NMR analysis.

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I am doing pyrrole chemistry for a while now and there is a quite interesting reaction with this. When I synthesize freshly a pyrrole (with free N-H) and add sodium-hydride, during the formation of the N-Na salt of the pyrrole an intense blue color appears as seen on the picture, but it fades to give a yellowish solution as the gas evolution stops. And it only works if the pyrrole is freshly prepared and it is in a pure form.

The color reminds me to the classic experiment, the solvated electron, what could be done by dissolving a piece of alkali metal in liquid ammonia.

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From the previously prepared sodium methoxide solution (first pics) a heterocyclic compound was prepared by a base catalyzed condensation.

This is one of the worst reactions what I usually perform during the preparation of a substituted pyrrole. When the sodium salt of the heterocycle precipitates (that yellow thing on the third pics) I have to remove most of the solvent before the workup. The only problem is, that the yellow compound with the methanol behaves like butter, so it’s impossible to remove all of the solvent with vacuum and I can’t use heat, since the compound readily decomposes. 

After adding acids and water to neutralize the solution during the workup (last pics) the product should precipitate as a white crystalline solid. As seen this step in this case failed to give white crystals, but I obtained a lot off-white/brown solid floating in the solution):

“Darth Maul” 9x12 watercolor painting. 🎨


I used a lot of “hematite genuine in this piece to give it the dark tones. Maybe 4 or 5 layers of it. Then pyrrol red for his face.

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