Copper(I) Cyanide

Other Names:

Cuprous cyanide

General Information:

Structure:

CAS Number: 544-92-3

Molecular Wieght: 89.563 g/mol

Appearance: Off-white to pale yellow powder

Chemical Formula: CuCN

Melting Point: 474 C

Common Uses:

Reagent for SNAr reactions where nitrile products are desired

Procedure excerpt:

To a solution of the SM (3.5 g, 7.14 mmol) in pyridine (10 mL) was added CuCN (636 mg, 7.14 mmol) at RT. The reaction mixture was stirred at 100 C for 16 h. After concentration . . .

[full procedure]

Reagent for Sandmeyer reactions where nitrile products are desired

Procedure excerpt:

To a suspension of CuCN (13.6 g, 152 mmol) in ACN (500 mL) was added isoamyl nitrite (25.4 mL, 190 mmol). A solution of the SM (20.0 g, 127 mmol) in ACN (100 mL) was . . .

[full procedure]

Safety:

Copper(I) cyanide is highly toxic. Contact with acids liberates a highly toxic gas.

References:

1) Patent Reference: WO2016011390, page 133, (20.2 MB)

2) Patent Reference: WO2014201173, page 239, (19.7 MB)

3) Wikipedia: Copper(I) cyanide (link)

4) www.sigmaaldrich.com: Copper(I) cyanide (link)