Can STAB replace NaBh4? cas：56553-60-7

[HerrHaber]

STAB is far more expensive as far as I know and NaBH4 is pretty good for your purpose

 

[UWe9o12jkied91d]

china has it for same price, im not sure who you are talking to but it won't reduce nitro, only ketones.

 

[UWe9o12jkied91d]

Yes, I have updated everybody on the status of this.My findings were that it can't reduce nitro to amino but for the anhydrous imine ways it is good and very mild.
There are reports of it in literature reducing nitro to amino but in the presence of acetic acid, which I have not tried.

 

[ZRG]

I don't know chemistry very well, anyway, the circuit using p2np, STAB and copper hydride is restored without Swiss brain, right?

 

[ZRG]

There might be something wrong with my translation, I mean p2np can't be reduced to amphetamine using STAB, right?

 

[UWe9o12jkied91d]

No, it cannot under normal conditions from my findings.There is literature that says it can in presence of GAA but I haven’t tried.

 

[ZRG]

Well, I still can't find the answer I'm looking for, because no one has tried

 

[UWe9o12jkied91d]

Do you think I’m relating to you from a dream? I have tried and it did not work, probably with acetoc acid will work to some degree but not satisfactory.
Short answer: No.

 

[K-Cyanide]

FYI if anyone needs STAB, it can be prepared quite easily with Toluene (or THF) , NaBH4 and GAA in stoichiometric amounts. Here is a brief write up:

Preparation of Sodium Triacetoxyborohydride (STAB)

To a suspension of 37,83 g (1 mol) Sodium borohydride in 500 ml dry Toluene is added 180,12 g ( 3 mol) GAA dropwise during vigorous stirring. The temperature is held below 30°C with external cooling when needed. When the gas evolution ceases, about 20 minutes, the suspended Sodium Triacetoxyborohydride (STAB) is isolated by vacuum filtration and washed once with dry EtOAc. The filtercake is dried to constant weight under vacuum.

Yield: Close to quantitative, if dry reagents are used and the reagents are measured out accurately.

 

[41Dxflatline]

There's other sources of borane too. Decaborane maybe? Tetrahydroxydiboron? Maybe aminodiboranates which can be synthesized somewhat easily from ammonia borane. See Page 306 https://core.ac.uk/download/4824361.pdf I'm not a chemist so I don't know how well these work on nitro compounds.

STAB / NaBH4 comparisons: https://www.organic-chemistry.org/synthesis/C1N/amines/reductive-amination-guide.pdf
Interesting STAB bits such as ways to significantly shorten reaction times, why GAA is used: https://www.researchgate.net/publication/286303639_Boron_reagents_for_reductive_amination