[Enantiomer]

Hello all,

I was planning on using copper cyanide in place of sodium cyanide (due to it being slightly safer) for an Sn2 reaction to displace a 1° bromoalkane, however I'm concerned it may not work as well due to the fact that similiar reactions require the reaction to be heated, and I'm mildly worried that the copper may complex to the newly formed nitrile with the addition of heat, am worried about nothing, or is there something else I should be worried about?

[discodermolide]

Hello all,

I was planning on using copper cyanide in place of sodium cyanide (due to it being slightly safer) for an Sn2 reaction to displace a 1° bromoalkane, however I'm concerned it may not work as well due to the fact that similiar reactions require the reaction to be heated, and I'm mildly worried that the copper may complex to the newly formed nitrile with the addition of heat, am worried about nothing, or is there something else I should be worried about?

What solvent are you going to use?

[Enantiomer]

I have not tested the solubility of CuCN yet, but I was going to attempt DMSO

[discodermolide]

I have not tested the solubility of CuCN yet, but I was going to attempt DMSO

May not that soluble, some will dissolve especially at higher temp. worth giving the reaction a try.

[zoork34]

Why is copper cyanide any safer?  The danger with cyanide salts is forming HCN under acidic conditions, and that would occur regardless of the cation.  I would be EXTREMELY careful with dissolving a cyanide salt in DMSO since DMSO will absorb right through your skin and take anything with it that is dissolved.  Double glove your hands and use a lab coat with complete arm coverage.