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shanmugapriya
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[*] posted on 11-9-2013 at 15:56
sodiumdithionate


Can anyone of you tell me procedure for reduction of nitro to amine by sodiumdithionate. plz
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[*] posted on 11-9-2013 at 22:47


Dithionate, S2O6(2-), is not a reductor, it is nearly as inert as sulfate. Only strong oxidizers are capable of oxidizing the dithionate ion to sulfate ion.




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[*] posted on 12-9-2013 at 00:36


I would be curious if you know any reactions that can be done with dithionate.
Perhaps with acetone? (reaction might be slow)

Elemental iodine spontaneously reacts with acetone. And sulfur will oxidize anhydrous hydrogen iodide.

[-]O-SO2-S-CH2-CO-CH3



[Edited on 12-9-2013 by AndersHoveland]
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[*] posted on 12-9-2013 at 02:30


I once purchased 100 grams of potassium dithionate, but I have to conclude that this chemical is not very interesting. It does react with anything, I have not found any interesting redox chemistry, nor any formation of precipitates or complexes. It is remarkably inert.



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Dr.Bob
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[*] posted on 12-9-2013 at 10:13


It is used to reduce aromatic nitro compounds to anilines in some cases. But it requires heat, time and the right solvent. There are some cases in which that works without affecting double bonds, benzyl esters and other easily reduced functional groups. It is also used in the synthesis of luminol from 3-nitrophthalic hydrazide in one of the older Fieser organic texts. But it does go bad over time, I believe, due to air oxidation.

If you want procedures, just Google "sodium dithionite reduction of nitro compounds"or look in SciFinder.
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[*] posted on 12-9-2013 at 10:26


Quote: Originally posted by Dr.Bob  
It is used to reduce aromatic nitro compounds to anilines in some cases.

I think I would have read about it, if sodium dithionate would be able to reduce anything organic. Do you have any reference at all?
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It is also used in the synthesis of luminol from 3-nitrophthalic hydrazide in one of the older Fieser organic texts.

No. Sodium dithionite is used in that synthesis.
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If you want procedures, just Google "sodium dithionite reduction of nitro compounds"or look in SciFinder.

That wont help much as the question is about procedures using sodium dithionate. If the original poster was interested in the dithionite, he would not be asking for examples here. Already a google search gives tons of examples.




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[*] posted on 12-9-2013 at 11:10


Maybe the OP made a typo or does not know the difference between dithionite and dithionate. Dithionite is the ion S2O4(2-), which is a strong and fast acting reductor, which is very unstable in acidic solutions (gives rise to very nasty and smelly sulfurous compounds). Dithionate is the ion S2O6(2-) and this is a rather tame and inert ion, both at high pH and at low pH. I have not found any interesting reactions with this ion and the stuff now is sitting on the shelve, waiting for a nice application or demonstration. Even a strong oxidizer like KMnO4 has difficulty oxidizing dithionate, it requires heating and the reaction is slow.

If you use dithionite, then be careful. The sodium salt of this is quite dangerous. It gives off very pungent fumes and especially if it is damp it may become pyrophoric and inflame spontaneously when brought in contact with air! I have some of this salt and it must be stored in a very tightly stoppered bottle!




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[*] posted on 12-9-2013 at 16:44


Thank you for the kind replies. sodiumdithionate is not workable one. Can i make use of sodiumdithionite for reduction of nitro group. My friend suggest me to use sodiumdithionite with sodiumbicarbonate in THF/Water system. I have done but no reaction carried out. Kindly propose the method to improve the reduction.

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[*] posted on 12-9-2013 at 22:51


Please tell the precise compound to be reduced. Not all nitro-compounds can be treated in the same way, more background information is needed for a useful and detailed answer.



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[*] posted on 13-9-2013 at 06:43


Sorry, I missed the spelling being dithionate. I have never even heard of that ion (S2O6)-2, and given the spelling on here, I would have chalked it to being a typo if I had noticed it. That would be a very weak reducing agent indeed. I was referring to dithionite, which works great for some reductions. Sorry again for replying when tired, I did not catch the spelling.
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