199787-69-4

Usage

Physical form

white crystalline solid

Uses

various pharmaceutical and chemical synthesis applications, intermediate in the preparation of pharmaceuticals (antifungal agents, antiviral drugs), catalyst and reagent in organic synthesis processes

Stability

relatively stable under normal conditions

Safety precautions

potential to cause skin irritation and other harmful effects if not properly used and stored.

Upstream product

• 892-20-6 triphenylstannane 
• 151515-23-0 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene 

Downstream Products

• 1287239-95-5 B(O)N₂C₃H(CH₃)(CH₂)(C₆H₃(CH(CH₃)2)2)2^(1-)*N₂C₃H(CH₃)2(CH(CH₃)2)2⁽¹⁺⁾=BO(C₄₀H₆₁N₄) 

Relevant academic research and scientific papers

To Rearrange or not to Rearrange: Reactivity of NHCs towards Chloro- and Hydrostannanes R2SnCl2(R = Me, Ph) and Ph3SnH

The reaction of 1,3-diisopropylimidazolin-2-ylidene (iPr2Im) with diphenyldichlorostannane and dimethyldichlorostannane, respectively, leads to the formation of the adducts (iPr2Im)·SnPh2Cl2(1) and (iPr2Im)·SnMe2Cl2(2). These compounds are stable in solution to temperatures up to 80 °C for several days and rearrangement to backbone-tethered bis(imidazolium) salts or ring expansion reaction to six membered heterocyclic rings was not observed. The reaction of iPr2Im with triphenylstannane Ph3SnH leads to reductive dehydrocoupling of the stannane to yield distannane Sn2Ph6and iPr2ImH2. Thus, the reactivity of these tin compounds is completely different compared to those of the lighter congener silicon, for which rearrangement (chlorides) and NHC ring expansion (hydrides) was reported earlier.