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73328

Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

Synonym(s):

Cyanotrimethylsilane, TMSCN

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About This Item

Linear Formula:
(CH3)3SiCN
CAS Number:
Molecular Weight:
99.21
Beilstein:
1737612
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

Assay

≥95% (GC)

form

liquid

refractive index

n20/D 1.392 (lit.)

bp

114-117 °C (lit.)

mp

8-11 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

SMILES string

C[Si](C)(C)C#N

InChI

1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3

InChI key

LEIMLDGFXIOXMT-UHFFFAOYSA-N

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Application

Trimethylsilyl cyanide (TMSCN) can be used as a reagent in the:
  • Cyanosilylation of carbonyl compounds using various catalysts.
  • Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.
  • Cyanation of aryl halides using palladium-complex as a catalyst.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Liq. 2

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F - closed cup

Flash Point(C)

1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al (salen)/triphenylphosphine oxide
Kim SS and Kwak Ju M
Tetrahedron, 62(1), 49-53 (2006)
Indium tribromide: a highly effective catalyst for the addition of trimethylsilyl cyanide to ?-hetero-substituted ketones
Bandini M, et al.
Tetrahedron Letters, 42(16), 3041-3043 (2001)
A convenient and efficient procedure for the palladium-catalyzed cyanation of aryl halides using trimethylsilylcyanide
Sundermeier M, et al.
Journal of Organometallic Chemistry, 684(1-2), 50-55 (2003)
Dinuclear {(salen)Al} complexes display expanded scope in the conjugate cyanation of alpha,beta-unsaturated imides.
Clément Mazet et al.
Angewandte Chemie (International ed. in English), 47(9), 1762-1765 (2008-01-26)
Alessandro Sacchetti et al.
Organic & biomolecular chemistry, 9(15), 5515-5522 (2011-06-21)
We investigated the Strecker-type reaction of isatin derived chiral ketimines with TMSCN in the presence of a Lewis acid. The desired α-amino nitriles have been obtained in good yields with moderate diastereoselectivity. Further elaboration of the cyanide group allowed the

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