(TRIMETHYLSILYL)ACETONITRILE Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich

(TRIMETHYLSILYL)ACETONITRILE Usage And Synthesis

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.]

(TRIMETHYLSILYL)ACETONITRILE(18293-53-3)Related Product Information

• Trimethylsilyl cyanide
• TRIMETHYLSILANE
• ETHANE
• Chlorine dioxide
• Clotrimazole
• FERROUS SULFATE
• Bromotrimethylsilane
• ETHYLTRIMETHYLSILANE
• Tetramethylsilane
• ETHYLDIMETHYLSILANE
• (TRIMETHYLSILYL)ACETONITRILE
• 2-Pyrrolizino-2-(trimethylsilyl)acetonitrile
• 2-(N-Benzyl-N-methylamino)-2-(trimethylsilyl)acetonitrile
• 2-(Dimethylamino)-2-(trimethylsilyl)acetonitrile
• 2-(Diethylamino)-2-(trimethylsilyl)acetonitrile
• 2-Piperidino-2-(trimethylsilyl)acetonitrile
• 2-(N-Benzyl-N-ethylamino)-2-(trimethylsilyl)acetonitrile
• 2-[N-(4-Methoxybenzyl)-N-methyl-amino]-2-(trimethylsilyl)acetonitrile