Trimethylsilyl Cyanide

Other Names:

Cyanotrimethylsilane

Trimethylsilylnitrile

TMS cyanide

TMSCN

General Information:

Structure:

CAS Number: 7677-24-9

Molecular Weight: 99.21 g/mol

Common Uses:

Reagent that acts as a source of cyanide for substitution reactions

Procedure excerpt:

. . . the SM (80.0 g, 286 mmol) and TMSCN (28.2 g, 286 mmol) in ACN (600 mL) was stirred at RT for 30 min. The mixture was cooled to 0 C and treated with TBAF . . .

[full procedure]

Reagent that acts as a source of cyanide for SNAr reactions

Procedure excerpt:

A mixture of the SM (150 mg, 0.36 mmol), TBAF (281 mg, 1.08 mmol), and TMSCN (107 mg, 1.08 mmol) in DMF (3 mL) was stirred at 100 C for 1 h. After cooling . . .

[full procedure]

References:

1) Patent Reference: WO2016014463, page 101, (6.7 MB)

2) Patent Reference: WO2016011390, page 151, (20.2 MB)

3) Wikipedia: Trimethylsilyl cyanide (link)

4) www.sigmaaldrich.com: Trimethylsilyl cyanide (link)