Sciencemadness Discussion Board

Peroxides and HBr

killswitch - 20-2-2013 at 08:05

The standard synthesis for TATP and HMTD call for HCl and H2O2. It occurs to me that using HBr with H2O2 induces the formation of Br. radicals. How would this affect the products?

I'm guessing that brominating any of the hydrogens would result in even weaker peroxide bonds than usual. However, Br is heavy enough that it might keep the product from sublimating.

I don't have any HBr, so I can't test this out. Anyone have any ideas?

P.S. I'm trying to recall the name of the explosive compound that contains nitro, nitric ester, and nitramine groups all on one molecule. Anyone remember the name of that one?

[Edited on 20-2-2013 by killswitch]

Adas - 20-2-2013 at 08:29

HBr and HI might get oxidized, thus the peroxide would be reduced. I would not recommend to use them.

Motherload - 20-2-2013 at 09:19

You will most likely end up with free elemental Br or I
They might react with acetone to form a variety of haloacetone compounds along with haloform.

killswitch - 21-2-2013 at 09:38

This line of thinking came up when I was introduced to anti-Markovnikov bromination via the HBr + H2O2 method.

AndersHoveland - 21-2-2013 at 16:23

Sodium bromide is easily oxidized by hydrogen peroxide to bromine, even when the solution is only slightly acidic.
Sodium bisulfate works well. I have used this reaction many times.

[Edited on 22-2-2013 by AndersHoveland]

Adas - 22-2-2013 at 07:01

Quote: Originally posted by AndersHoveland  
Sodium bromide is easily oxidized by hydrogen peroxide to bromine, even when the solution is only slightly acidic.
Sodium bisulfate works well. I have used this reaction many times.

[Edited on 22-2-2013 by AndersHoveland]


From my experience, sodium bisulfate causes only a very slow reaction and tends to form a separate phase ("salting out"?). I think there are better choices. HCl is the best, IMO.