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Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

Synonym(s):

Cyanotrimethylsilane, TMSCN

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About This Item

Linear Formula:
(CH3)3SiCN
CAS Number:
7677-24-9
Molecular Weight:
99.21
Beilstein/REAXYS Number:
1737612
EC Number:
231-657-3
MDL number:
MFCD00001765
UNSPSC Code:
12352100
PubChem Substance ID:
57652474
NACRES:
NA.22

grade

technical

Quality Level

100

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.

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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

EUH014,EUH029

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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Certificates of Analysis (COA)

Lot/Batch Number
STBL1606
STBK9203
STBK3856
STBK3489
STBK3412

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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)
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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