# Copper Cyanide

## Copper(I) cyanide is an inorganic compound with the formula CuCN. This off-white solid occurs in two polymorphs; impure samples can be green due to the presence of Cu(II) impurities.

### Organic Synthesis

CuCN is a prominent reagent in organocopper chemistry. It reacts with organolithium reagents to form "mixed cuprates" with the formulas Li[RCuCN] and Li2[R2CuCN].

The use of CuCN revolutionized the deployment of simpler organocopper reagents of the type CuR and LiCuR2, the Gilman reagents. In the presence of cyanide, these mixed cuprates are more readily purified and more stable.

The mixed cuprates Li[RCuCN] and Li2[R2CuCN] function as sources of the carbanions R−, but with diminished reactivity compared to the parent organolithium reagent. Thus they are useful for conjugate additions and some displacement reactions. Addition of CuCN to[clarification needed]

CuCN also forms silyl and stannyl reagents, which are used as sources of R3Si− and R3Sn−.

CuCN is used in the conversion of aryl halides to nitriles.

### Industrial uses for Copper Cyanide

The compound is useful as a catalyst, in electroplating copper, and as a reagent in the preparation of nitriles.

Cuprous cyanide is used for electroplating copper.

CuCN is a prominent reagent in organocopper chemistry. It reacts with organolithium reagents to form "mixed cuprates" with the formulas Li[RCuCN] and Li2[R2CuCN]. The use of CuCN revolutionized the deployment of simpler organocopper reagents of the type CuR and LiCuR2, the Gilman reagents. In the presence of cyanide, these mixed cuprates are more readily purified and more stable.

The mixed cuprates Li[RCuCN] and Li2[R2CuCN] function as sources of the carbanions R−, but with diminished reactivity compared to the parent organolithium reagent. Thus they are useful for conjugate additions and some displacement reactions. Addition of CuCN to[clarification needed] [11]

CuCN also forms silyl and stannyl reagents, which are used as sources of R3Si− and R3Sn−.[12]

CuCN is used in the conversion of aryl halides to nitriles.

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