(TRIMETHYLSILYL)ACETONITRILE

Synonym(s):(Cyanomethyl)trimethylsilane;TMSAN

CAS NO.：18293-53-3
Empirical Formula: C5H11NSi
Molecular Weight: 113.23
MDL number: MFCD00001882
EINECS: 242-169-5
SAFETY DATA SHEET (SDS)
Update Date: 2026-05-28 00:24:57

What is (TRIMETHYLSILYL)ACETONITRILE?

Physical properties

bp 84–85 °C/54 mmHg, 66 °C/35 mmHg, 65–70 °C/20 mmHg;3 d 0.827 g cm?3.

The Uses of (TRIMETHYLSILYL)ACETONITRILE

(Trimethylsilyl)acetonitrile has been used in catalytic cyanomethylation of various carbonyl compounds in the presence of Lewis bases.

The Uses of (TRIMETHYLSILYL)ACETONITRILE

α-carbanion is a useful alternative to LiCH2CN for nucleophilic cyanomethylation; (Z)-selective Peterson alkenation). Trimethylsilylacetonitrile participates in the following synthesis reactions: Metalation, Peterson Alkenation (Cyanomethylenation), Michael Addition, Reactions with Other Electrophiles, Cyanomethylation, Metal-Catalyzed Reactions etc.

Preparation

From chlorotrimethylsilane, zinc, and XCH2CN, (X = Cl, 61% yield; X = Br, 81% yield).

Purification Methods

Check if NMR and IR spectra show impurities; if present dissolve it in *C6H6 (10volumes), wash it with buffer (AcOH/AcONa pH ca 7) several times, dry (CaCl2) it, evaporate and distil it. IR: (CCl4) 2215 (CN) cm-1, NMR (CCl4): 0.23 (s, 9H, SiMe3), and 1.53 (s, 2H, CH2CN). [Matsuda et al. J Chem Soc, Perkin Trans 1 26 1979, Beilstein 4 IV 3974.]

Properties of (TRIMETHYLSILYL)ACETONITRILE

Boiling point:	65-70 °C20 mm Hg(lit.)
Density	0.827 g/mL at 25 °C(lit.)
refractive index	n20/D 1.420(lit.)
Flash point:	122 °F
storage temp.	Sealed in dry,Room Temperature
solubility	Sol most common organic solvents.
form	Liquid
color	Clear colorless to straw
Specific Gravity	0.829
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
BRN	1738845

Safety information for (TRIMETHYLSILYL)ACETONITRILE

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H226:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P311:Call a POISON CENTER or doctor/physician. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.