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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

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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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)
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)
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)
Gang Chen et al.
Organic letters, 10(20), 4573-4576 (2008-09-24)
A convenient and efficient synthesis of alpha-aryl nitriles was developed by direct cyanation of alcohols with TMSCN under the catalysis of Lewis acid. Using 5-10 mol % of InBr3 as the catalyst, a variety of benzylic alcohols can be converted
Siddhartha R Shenoy et al.
Journal of the American Chemical Society, 128(26), 8671-8677 (2006-06-29)
The limitations of stereoelectronic models in assessing the stereoselective nucleophilic substitution reactions of cyclic oxocarbenium ions at high reaction rates are discussed. Evidence is provided suggesting that the diastereoselectivity of nucleophilic substitution reactions is attenuated at the limits of diffusion

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