(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: 2026-01-13 11:18:30
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 | n |
| 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. |
Computed Descriptors for (TRIMETHYLSILYL)ACETONITRILE
| InChIKey | WJKMUGYQMMXILX-UHFFFAOYSA-N |
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