Trimethylsilyl cyanide
Synonym(s):Cyanotrimethylsilane;TMSCN
- CAS NO.:7677-24-9
- Empirical Formula: C4H9NSi
- Molecular Weight: 99.21
- MDL number: MFCD00001765
- EINECS: 231-657-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-07 12:04:01
What is Trimethylsilyl cyanide?
The Uses of Trimethylsilyl cyanide
Reacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.
Trimethylsilyl cyanide (TMSCN) participates in carbonyl aminomethylation via α-silyloxy nitriles.
TMSCN can be used as a reagent in the:
Trimethylsilyl cyanide was used in the second step of an oxidative Michael addition of cyanide anion to Baylis–Hillman adducts. The importance of the addition of cyanide to α,β-unsaturated carbonyl derivatives is that the products can be converted into a variety of compounds including γ-aminobutyric acids. The reaction took place in a liquid ionic medium ([bmim]Br), which was reused several times without losing its activity. The β-cyano carbonyl compounds were obtained with high regioselectivity and yields (>79%).
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.
The Uses of Trimethylsilyl cyanide
A solution of the SM (80.0 g, 286 mmol) and TMSCN (28.2 g, 286 mmol) in ACN (600 mL) was stirred at RT for 30 min. The mixture was cooled to 0 C and treated with TBAF (74.6 g, 286 mmol). The reaction mixture was stirred for 12 h, after which time it was diluted with H2O and extracted with EtOAc. The org layer was separated, dried (Na2SO4), and concentrated. The residue was purified by silica gel flash chromatography to provide the product. [39 g, 60%]
Properties of Trimethylsilyl cyanide
Melting point: | 8-11 °C(lit.) |
Boiling point: | 114-117 °C(lit.) |
Density | 0.793 g/mL at 20 °C(lit.) |
Flash point: | 34 °F |
storage temp. | Inert atmosphere,2-8°C |
solubility | Miscible with organic solvents. |
form | liquid |
color | Yellow |
Water Solubility | reacts |
Sensitive | Moisture Sensitive |
Safety information for Trimethylsilyl cyanide
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06 Environment GHS09 |
GHS Hazard Statements |
H225:Flammable liquids H410:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
Computed Descriptors for Trimethylsilyl cyanide
InChIKey | LEIMLDGFXIOXMT-UHFFFAOYSA-N |
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