I found OTC sources for taurine (NH2CH3CH2SO2OH) and MSM (dimethylsulfone, (CH3)2SO2 a.k.a. methylsulfonylmethane). Both are said to be beneficial
food supplements. I do not want to discuss whether that is true or not, but what I do want to discuss is whether these chemicals can be interesting
for home chemistry purposes. Both have a simple structure and are available at (nearly) 100% purity OTC.
Does anyone have any experience with these, or know of any synthesis of other interesting chemicals. I have been looking around on sciencemadness and
internet in general, but only very little information can be found. Wikipedia also concentrates on the health effects of these chemicals and hardly
discusses other aspects of their chemistry.watson.fawkes - 4-7-2013 at 10:52
As for MSM, the Wikipedia page does mention its ligand chemistry. Also, you likely don't need it yourself, but a process for converting it to DMSO
might be useful for others.bfesser - 4-7-2013 at 11:24
<a href="http://en.wikipedia.org/wiki/Methylsulfonylmethane" target="_blank">Methylsulfonylmethane</a> <img src="../scipics/_wiki.png"
/> also mentions it's use as a high temperature solvent for organic reactions (mpt 109°C, bp 238°C).
Several interesting titles appear in the first few pages of a Google Scholar search for <a
href="http://scholar.google.com/scholar?q=dimethylsulfone" target="_blank">"dimethylsulfone"</a>:<ul><li><a
href="http://dx.doi.org/10.1016/S1352-2310(99)00407-0" target="_blank"><strong>Atmospheric gas-phase reactions of dimethylsulphoxide and
dimethylsulphone with OH and NO<sub>3</sub> radicals, Cl atoms and ozone</strong></a></li><li><a
href="http://dx.doi.org/10.1007/s00894-008-0279-y" target="_blank"><strong>Why are dimethyl sulfoxide and dimethyl sulfone such good
solvents?</strong></a></li><li><a href="http://dx.doi.org/10.1021/ja00267a006" target="_blank"><strong>Theoretical
study of carbanions and lithium salts derived from dimethyl sulfone</strong></a></li><li><a
href="http://dx.doi.org/10.1149/1.1354616" target="_blank"><strong>Electrolytic Codeposition of Silica Particles with Aluminum from
AlCl<sub>3</sub>-Dimethylsulfone Electrolytes</strong></a></li></ul>Variations of spelling and naming may aid in
further searching.
As for <a href="http://en.wikipedia.org/wiki/Taurine" target="_blank">taurine</a> <img src="../scipics/_wiki.png" />, nothing
springs to mind.
[Edited on 7/9/13 by bfesser]sonogashira - 4-7-2013 at 12:26
This is probably the best source of information online: http://redironhosting.com/~gaylordc/uploads/images/pdfs/lite...
They have good information on their website for DMSO chemistry too: http://www.gaylordchemical.com/index.php?page=msds-specifica...
I have some papers on using the dimethyl sulphone analog of the dimsyl anion in organic synthesis, if it's of interest to you (probably not). It's a
very nice material to work with. I've used it in some high temperature experiments as an inert, stable polar aprotic solvent. It's very good for
introducing fluorine into organic compounds, through displacement of the chlorine etc. It's very cleanly removed post-reaction by (entrainer [air])
sublimation at it's melting point, or higher. It will dissolve in water easily also. It forms massive crystals from almost anything. It smells
slightly of cabbage at boiling point! It can be used to remove trace aromatic compounds from aliphatic ones, due to affinity for aromatic rings. If
you are looking for information on it's uses you can look up sulfolane, which is very similar and used interchangeably in most reactions. Sulfolane is
fluid at room temperature, so it tends to be used more often than DMSO2.
[Edited on 4-7-2013 by sonogashira]
[Edited on 4-7-2013 by sonogashira]bbartlog - 4-7-2013 at 12:31
- once to try decarboxylation of salicylic acid (but I heated it too high here, more or less to reflux)
- once as a 'solvent' for the reaction of sodium acetate and ammonium chloride. Watching the reaction I don't know that a lot of solvation actually
took place, but it may still have mechanically slowed the escape of some of the volatile components.
- once just to see what would happen if I heated sulfur and TCCA together to over 200C
None of the results were terribly interesting, though I did succeed in producing acetamide in the second case. But a any rate it does work as a stable
high-boiling solvent; though it is not easy to find information on what substances you can expect to dissolve in it.Nicodem - 4-7-2013 at 14:05
Taurine can be used to make numerous coordination compounds. There are plenty examples in the literature, for example a cobalt compound (DOI:
10.1107/S1600536811039390).
It can be used to prepare imines from salicaldehyde which can again act as ligands for various metals or be reduced to the N-(2-hydroxybenzyl)-taurine
with NaBH4 (European Journal of Inorganic Chemistry 2005, 4635-4645). It also forms stable imines or their salts or coordination compounds with plenty
of other aromatic aldehydes.
It can be functionalized at the amino group, for example to the corresponding urea using KOCN (Synthesis 1988, 810-813).
Of course, there are thousands of other possible uses of taurine in synthesis.
As for dimethylsulfone, there is a review of its applications in synthesis in e-EROS. That should be a good start. Most of its chemistry requires
strong bases for its deprotonation (hydroxides can be used in some cases, but otherwise stronger bases are most commonly applied). The carboanion then
reacts with all kinds of electrophiles (for example, with aldehydes and ketones as described in DOI: 10.1021/jo051947s).Crowfjord - 8-7-2013 at 18:05
Wow, thanks for that last reference, Nicodem! I shall have to download the entire article later to make sure, but that looks like it could be a good
means to synthesize dienes for use in Diels-Alder reactions. sargent1015 - 8-7-2013 at 18:59
Taurine can be used to make numerous coordination compounds. There are plenty examples in the literature, for example a cobalt compound (DOI:
10.1107/S1600536811039390).
Well, now I need to add that to my list of compounds to coordinate with. If it's not a big secret, who is your supplier Woelen? solo - 8-7-2013 at 19:11
Reference Information
Studies of the Condensation of Sulfones with Ketones and Aldehydes
Michael E. Garst,† Lloyd J. Dolby J. Org. Chem.
2006, 71, 553-556
DOI:10.1021/jo051947s
Copper(II) Complexes of Schiff-Base and Reduced Schiff-Base Ligands: Influence of Weakly Coordinating Sulfonate Groups on the Structure and
Oxidation of 3,5-DTBC
Bellam Sreenivasulu,[a] Muthalagu Vetrichelvan Eur. J. Inorg. Chem.
2005, 4635–4645
DOI: 10.1002/ejic.200500638
Attachment: php6Ye5Xs (1018kB) This file has been downloaded 457 times
Fantasma4500 - 9-7-2013 at 02:02
call me closeminded or whatever, but wouldnt it be possible to nitrate taurine?
dont know what the actual rules are for a nitration to take place
in cellulose it replaces OH atoms, and the taurine has OH atoms available, it also has nitrogen as NH2
would be exotic for sure if possible
NO3 is a stronger ion than SO2, if im not mistakenbfesser - 9-7-2013 at 06:30
<strong>R-OH</strong> is not an <a href="http://en.wikipedia.org/wiki/Atom" target="_blank">atom</a> <img
src="../scipics/_wiki.png" />; it's the <a href="http://en.wikipedia.org/wiki/Hydroxyl" target="_blank">hydroxyl</a> <img
src="../scipics/_wiki.png" /> <a href="http://en.wikipedia.org/wiki/Functional_group" target="_blank">functional group</a> <img
src="../scipics/_wiki.png" />:
An <a href="http://en.wikipedia.org/wiki/Alcohol" target="_blank">alcohol</a> <img src="../scipics/_wiki.png" />:
<strong>CH<sub>3</sub>CH<sub>2</sub>-OH</strong> (ethanol)
A <a href="http://en.wikipedia.org/wiki/Carboxylic_acid" target="_blank">carboxylic acid</a> <img src="../scipics/_wiki.png" />:
<strong>CH<sub>3</sub>CO-OH</strong> (ethanoic acid)
A <a href="http://en.wikipedia.org/wiki/Phenols" target="_blank">phenol</a> <img src="../scipics/_wiki.png" />:
<strong>C<sub>6</sub>H<sub>5</sub>-OH</strong> (phenol)
<strong>R-NH<sub>2</sub></strong> is a primary <a href="http://en.wikipedia.org/wiki/Amine"
target="_blank">amine</a> <img src="../scipics/_wiki.png" />.
[Edited on 7/9/13 by bfesser]Acidum - 9-7-2013 at 12:39
Also, taurin doesn't have OH groups either. It has SO3H, CH2 and NH2 groups. N nitration is not easily accomplished.
You should definitely learn more about nitrations and organic syntheses...
