(TRIMETHYLSILYL)ACETONITRILE Property

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

InChIKey

WJKMUGYQMMXILX-UHFFFAOYSA-N

Safety

Hazard Codes 

T

Risk Statements 

10-23/24/25-36/37/38

Safety Statements 

26-36/37/39-45

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

21

TSCA 

No

HazardClass 

3.2

PackingGroup 

III

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P311Call a POISON CENTER or doctor/physician.

(TRIMETHYLSILYL)ACETONITRILE Chemical Properties,Usage,Production

Physical properties

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

Uses

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.

Uses

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

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.]