73328
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
231-657-3
Beilstein/REAXYS Number:
1737612
MDL number:
Assay:
≥95% (GC)
Form:
liquid
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
InChI key
LEIMLDGFXIOXMT-UHFFFAOYSA-N
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
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
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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)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 73328-50ML-F | 04061832867311 |
| 73328-250ML-F | 04061837507786 |