73328

Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

Synonym(s):
Cyanotrimethylsilane, TMSCN
Linear Formula:
(CH3)3SiCN
CAS Number:
Molecular Weight:
99.21
Beilstein/REAXYS Number:
1737612
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

technical

assay

≥95% (GC)

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.

Packaging

50, 250 mL in glass bottle

Signal Word

Danger

hazcat

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

Supp Hazards

EUH029

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 3

Flash Point(F)

33.8 °F

Flash Point(C)

1 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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)
Mikhail D Kosobokov et al.
The Journal of organic chemistry, 77(13), 5850-5855 (2012-06-20)
A new silicon reagent, difluoro(trimethylsilyl)acetonitrile, was prepared by insertion of difluorocarbene into silyl cyanide. The obtained silane served as a good cyanodifluoromethylating reagent toward aldehydes, N-tosylimines, N-alkylimines, and enamines under basic or acidic conditions.
Enantioselective synthesis of tertiary α-hydroxy phosphonates catalyzed by carbohydrate/cinchona alkaloid thiourea organocatalysts.
Shasha Kong et al.
Angewandte Chemie (International ed. in English), 51(35), 8864-8867 (2012-08-01)

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