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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)