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Author: Subject: the hunt for the reducing agent
CuReUS
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[*] posted on 17-10-2014 at 08:25


i know that silver diazonium compounds can explode ,but complexes themselves,that is news
i feel it is counter-intuitive ,as we are taught that complexes are very stable compounds(Fe(CN)64- is not toxic although it has cyanide ion
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zed
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[*] posted on 20-10-2014 at 15:53


Ummm. Don't let 'em dry out. Some of these complex ions, like to "simplify" themselves into materials that are very unstable.

As for Ferri-cyanides....they are sometimes utilized as components, in some impressive explosives.

Alas, we have gone way off topic. And, I'm not really an explosives guy. My interest is in avoiding explosions.

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CuReUS
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[*] posted on 23-10-2014 at 01:34


yesterday i saw nurdrage synthesis of luminol
http://www.youtube.com/watch?v=58Ve69s0qD0

he uses Na2S2O5 and Al to reduce the nitro to the amino to get luminol .:o

so can we use Na2S2O3 with Al to get the same result with 2,4 DAMP
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CuReUS
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[*] posted on 15-11-2014 at 21:44


in the hope of reviving this thread ,i ask a question that is bothering me for quite sometime now

how powerful a reducing agent is HI

can it reduce COOH to methyl directly (until recently i thought it couldn't but recently i read that it could.:o )

http://chemistry.tutorvista.com/organic-chemistry/carboxylic...
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CuReUS
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[*] posted on 28-12-2014 at 23:54


Quote: Originally posted by Nicodem  

Do you have a reference for a non-CTH or non-catalyzed reduction of nitroaromatics with H3PO2? I have only seen CTH reductions with this reagents


maybe you already know this reaction,but i am posting it anyway
read this article,they use H3PO2 along with HI to reduce aromatic nitro group

Attachment: molecules-19-08039-v2.pdf (403kB)
This file has been downloaded 575 times

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Nicodem
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[*] posted on 29-12-2014 at 05:24


Quote: Originally posted by CuReUS  
maybe you already know this reaction,but i am posting it anyway
read this article,they use H3PO2 along with HI to reduce aromatic nitro group

The article in Molecules 2014, 19, 8039-8050 mentions the reductions of some nitrophenols with hydriodic acid. The hypophosphorous acid appears to be there only to quench the iodine which is the side product of the reduction (while it also recycles the iodine back to HI). This example does not indicate that the hypophosphorous acid can reduce nitro groups. If anything, it might indicate the opposite.

Quote:
The nitrophenol compounds 8b–13b were then heated under reflux with 57% HI (10 mL) in the presence of 30% H3PO2 (1.0 mL).




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Dr.Bob
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[*] posted on 29-12-2014 at 12:47


There are much gentler ways to reduce nitro groups than "reflux with 57% HI (10 mL) in the presence of 30% H3PO2 (1.0 mL). " Sodium dithionate (Na2S2O5) works fine, even without Al (which I had not seen added before), Raney Nickel and many reductants, Sn, Fe, H2, etc. While it is always interesting to read about another essoteric method, I don't think 57% HI is any easier to find or use than other methods. I can't think of many things more common and iron and HCl, although I will admit that they form a mess and are not the ideal reducing agent, but a nitro group is pretty easy to reduce.
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CuReUS
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[*] posted on 29-1-2015 at 23:43


could someone explain why sometimes formic acid can be used as a reducing agent and sometimes Al/hg and acid is used to reduce imines.Both can reduce imimes,formic acid in eschenweiler-clarke and Al/hg +acid for reductive amination.so can they be used interchangebly ?
also,Zn/HCl can reduce C-C double bonds,but I think the yield will be small
https://books.google.co.in/books?id=AcpPyv0HWRsC&pg=SL1-...
go to the next page(A-98) and read the example of the clemmeson reduction of cyclic 1,3-diketone
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[*] posted on 30-1-2015 at 02:30


Quote: Originally posted by CuReUS  
in the hope of reviving this thread ,i ask a question that is bothering me for quite sometime now

how powerful a reducing agent is HI

can it reduce COOH to methyl directly (until recently i thought it couldn't but recently i read that it could.:o )

http://chemistry.tutorvista.com/organic-chemistry/carboxylic...


Apparently so. According to this (see pages 44 and 45 of the .pdf), at high enough temperatures, HI will completely reduce carboxylic acids and even polyaromatic hydrocarbons.

[Edited on 30-1-2015 by Darkstar]
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CuReUS
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[*] posted on 1-4-2015 at 02:03


can Drano be used as a reducing agent to reduce nitro to amine ?
I know that Metal/HCl and Metal/NaOH reductions on aromatic nitro compounds give different products,but has anyone ever tried it ?
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morganbw
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[*] posted on 1-4-2015 at 16:01


I have not. I generally run away from a chemical product that has additives.
That being said, perhaps it is worth a try????

[Edited on 2-4-2015 by morganbw]
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Chemosynthesis
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[*] posted on 1-4-2015 at 16:41


Drano is a company, not a single product.
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morganbw
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[*] posted on 1-4-2015 at 16:48


In a normal world Drano, clears drains, it it composed of not just NaOH.
Would you use a company to do a synth, or a product of said company?
I am confused by your post?

CuReUS ask a question, was it about a corporation or about a product?

[Edited on 2-4-2015 by morganbw]
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CuReUS
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[*] posted on 2-4-2015 at 04:53


sorry ,sorry everyone for the confusion .Of course I asked about the product -the drain cleaner. recently my house drain got blocked and I used drano(the powder form) to unblock it.I was impressed how vigorously the reaction was happening (the powder and the water) and it became hot very fast-like 25'c to 100'c in just 5 seconds :o
being an OTC minded guy,I immediately wondered whether it could be used for a nitro reduction, its dirt cheap.
but drano wiki says that they put NaNO3 in it to react with the H2 gas formed to covert from NO3- to NH3 to reduce an explosion risk
http://en.wikipedia.org/wiki/Drano#Crystal_Drano
I guess that washes all hopes down the drain :(

[Edited on 2-4-2015 by CuReUS]
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