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212849

Sigma-Aldrich

Trimethylsilyl cyanide

98%

Sinónimos:

Cyanotrimethylsilane, TMSCN

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About This Item

Fórmula lineal:
(CH3)3SiCN
Número de CAS:
7677-24-9
Peso molecular:
99.21
Beilstein/REAXYS Number:
1737612
EC Number:
231-657-3
MDL number:
MFCD00001765
UNSPSC Code:
12352100
PubChem Substance ID:
24852746
NACRES:
NA.22

Quality Level

200

assay

98%

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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General description

Trimethylsilyl cyanide participates in carbonyl aminomethylation via α-silyloxy nitriles.

Application

Trimethylsilyl cyanide was used:
  • for derivatization of complex metabolite mixtures by GC-MS
  • as cyanide source in enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones
  • as reagent for the cyanosilylation of aldehydes in near quantitative yield via catalysis by silylene-bridged rare earth oxide complexes
  • in asymmetric cyanosilylation with chiral dinuclear Ti(IV) complexes

Packaging

Packaging material contains granular sodium carbonate as a desiccant.

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

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Bekzod Khakimov et al.
Analytical and bioanalytical chemistry, 405(28), 9193-9205 (2013-10-05)
Reproducible and quantitative gas chromatography-mass spectrometry (GC-MS)-based metabolomics analysis of complex biological mixtures requires robust and broad-spectrum derivatization. We have evaluated derivatization of complex metabolite mixtures using trimethylsilyl cyanide (TMSCN) and the most commonly used silylation reagent N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA). For
Aurora Martínez-Muñoz et al.
Organic & biomolecular chemistry, 11(47), 8247-8255 (2013-10-30)
The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields
Synthetic applications of trimethylsilyl cyanide. Efficient synthesis of. beta.-aminomethyl alcohols.
Evans DA, et al.
The Journal of Organic Chemistry, 39(7), 914-917 (1974)
Tetrahedron Asymmetry, 17, 2328-2328 (2006)
Synthetic Communications, 36, 2483-2483 (2006)
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Reagents for C–C Bond Formation

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