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73328

Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

Synonym(s):

Cyanotrimethylsilane, TMSCN

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10 MG
$161.00

$161.00


Estimated to ship onMarch 23, 2025


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10 MG
$161.00

About This Item

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

$161.00


Estimated to ship onMarch 23, 2025


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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

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1 of 4

This Item
597475568979302
form

crystals, powder

form

powder

form

lyophilized powder

form

crystalline, crystals, powder or flakes

recombinant

expressed in E. coli

recombinant

expressed in E. coli

recombinant

expressed in E. coli

recombinant

expressed in E. coli

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

Trimethylsilyl cyanide (TMSCN) can be used as a reagent in the:
  • Cyanosilylation of carbonyl compounds using various catalysts.[1][2]
  • Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.[3]
  • Cyanation of aryl halides using palladium-complex as a catalyst.[4]

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

33.8 °F - closed cup

flash_point_c

1 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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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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