PROPARGYLTRIMETHYLSILANE Property

Melting point:

148-151 °C(Solv: ethyl ether (60-29-7))

Boiling point:

91-93 °C (lit.)

Density 

0.753 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.413(lit.)

Flash point:

13 °F

storage temp. 

-20°C

solubility 

sol ether, THF, CH2Cl2.

form 

Liquid

color 

Clear yellow

BRN 

2036316

CAS DataBase Reference

13361-64-3

EPA Substance Registry System

Silane, trimethyl-2-propynyl- (13361-64-3)

Safety

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

HazardClass 

3.1

PackingGroup 

II

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

PROPARGYLTRIMETHYLSILANE Chemical Properties,Usage,Production

Chemical Properties

Clear yellow liquid

Physical properties

bp 91–93 °C/760 mmHg; 40 °C/140 mmHg; d 0.753 g mL?1; nD 20 1.4140.

Uses

3-Trimethylsilyl-1-propyne is used as propargylation agent; allenylation agent; can give addition reactions on the triple bond. It takes part in the following reactions: Propargylation Reactions, Alkylation Reactions, Reactions with Epoxides,Reactions with Aldehydes and Ketones, Reactions with Chloroformates, Reactions with Polyoxymethylene and Amines, Allenylation Reactions, Substitution Reactions, Reactions with Acetals and Hemiacetals, Reactions with Aldehydes and Ketones, Reactions with in situ Generated Iminium and α-Acyl Iminium Ions, Reactions with Acid Chlorides, Reactions with Conjugated Heteroatomic Systems, Reactions of the Triple Bond etc.

Uses

Trimethyl(propargyl)silane is suitable for use in the synthesis of diverse end-functionalized (ω-carboxyl, ω-hydroxy, ω-methyl-vinyl, ω-trimethylsilane, and ω-glycidyl-ether) via ′′click′′ reaction. It may be used in the synthesis of γ-allenyl-GABA (γ-aminobutyric acid), via Lewis acid mediated reaction with ω-ethoxy lactams.

Preparation

The main method of preparation is shown in eq 1. The title reagent can be obtained by other methods, but in poor yields.

General Description

Trimethyl(propargyl)silane (2-Propynyl-trimethylsilane) is a clear colorless liquid and contains 500ppm of butylated hydroxytoluene (BHT) as stabilizer. It undergoes GaCl₃-catalyzed dehydrogenation reaction with aldimines to afford 4-methylquinoline.

Purification Methods

Fractionally distil it and add 2,6-di-tert-butyl-p-cresol (~0.5%) to stabilise it. [Petrov et al. Doklady Acad Nauk USSR 93 293 1953, cf Chem Abstr 48 13616 1954, Beilstein 4 IV 3938.]