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HomeProduct name list(TRIMETHYLSILYL)ACETONITRILE

(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: 2023-11-17 18:01:30
(TRIMETHYLSILYL)ACETONITRILE Structural

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)
ghs
Flame
Flammables
GHS02
ghs
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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