212849

Sigma-Aldrich

Trimethylsilyl cyanide

98%

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

Quality Level

assay

98%

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

25 g in Sure/Seal™
5 g in glass bottle

Signal Word

Danger

Supp Hazards

EUH029

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3384 3(6.1) / PGI

WGK Germany

WGK 3

Flash Point(F)

33.8 °F

Flash Point(C)

1 °C

Synthetic Communications, 36, 2483-2483 (2006)
Tetrahedron Asymmetry, 17, 2328-2328 (2006)
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)
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...

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