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73328

Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

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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

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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1 of 4

This Item
21284938652958825
vibrant-m

73328

Trimethylsilyl cyanide

vibrant-m

212849

Trimethylsilyl cyanide

vibrant-m

386529

Chlorotrimethylsilane

vibrant-m

58825

tert-Butyl isocyanoacetate

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

refractive index

n20/D 1.392 (lit.)

refractive index

n20/D 1.392 (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.422

density

0.793 g/mL at 20 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.97 g/mL at 20 °C (lit.)

form

liquid

form

liquid

form

liquid

form

-

bp

114-117 °C (lit.)

bp

114-117 °C (lit.)

bp

57 °C (lit.)

bp

50 °C/0.1 mmHg (lit.)

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.

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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Customers Also Viewed

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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)
Zhiguo Zhang et al.
The Journal of organic chemistry, 76(23), 9764-9776 (2011-10-21)
We report a new thiourea-Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction.
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

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