Trimethylsilylacetylene Chemical Properties

Melting point:

>0°C

Boiling point:

53 °C(lit.)

Density 

0.695 g/mL at 25 °C(lit.)

vapor pressure 

4.18 psi ( 20 °C)

refractive index 

n20/D 1.388(lit.)

Flash point:

<−30 °F

storage temp. 

Store below +30°C.

solubility 

Miscible with organic solvents.

form 

liquid

Specific Gravity

0.695

color 

colorless

Water Solubility 

reacts

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

906752

InChIKey

CWMFRHBXRUITQE-UHFFFAOYSA-N

CAS DataBase Reference

1066-54-2(CAS DataBase Reference)

NIST Chemistry Reference

(Trimethylsilyl)acetylene(1066-54-2)

EPA Substance Registry System

Trimethylsilylacetylene (1066-54-2)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 2

WGK Germany 

-

Hazard Note 

Flammable/Irritant

TSCA 

T

HazardClass 

3

PackingGroup 

II

HS Code 

29310095

MSDS

• Language:English Provider:Trimethylsilylacetylene
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Trimethylsilylacetylene Usage And Synthesis

Silican-protected group

Trimethylsilylacetylene is a silican-protected group, also known as trimethylethynylsilane, trimethylethynyl silicon and ethynyltrimethylsilane. It is a colorless transparent liquid at room temperature. It could be used to synthesize parazole by the addition of 1,3-bipolar ring of acetylene diazide. It is also the substrate of nickel catalyzed reaction and benzonitrile coupling reaction.

Application

• Common intermediate for asymmetric synthesis
• Silica reagent

Chemical Properties

CLEAR COLORLESS LIQUID

Physical properties

bp 53 °C; d 0.695 g cm?3.

Uses

(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone.

Uses

Ethynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes

Uses

Trimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.

General Description

Laser-induced polymerization of gaseous ethynyltrimethylsilane was used for efficient chemical vapour deposition of polycarbosilane films. Ethynyltrimethylsilane acts as substrate for nickel-catalyzed cross-coupling with benzonitriles.

Purification Methods

Distil it through an efficient column. The IR has bands at max 2041 (CC) and 3289 (C-H) cm-1. [Kr.hnke & Goss Chem Ber 92 30 1959, Beilstein 4 IV 3937.]

Trimethylsilylacetylene(1066-54-2)Related Product Information

• Methanesiliconic acid sodium salt
• hydroxytrimethylsilane
• N-(Trimethylsilyl)imidazole
• Azidotrimethylsilane
• Lithium bis(trimethylsilyl)amide
• Bis(trimethylsilyl)acetylene
• Hexamethyldisilazane
• Trimethylsilyl cyanide
• TRIMETHYLSILANE
• Triethylene glycol
• Methyltrioctylammonium hydrogen sulfate
• Trichloroacetyl isocyanate
• trimethyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane
• Trimethylammonium cyanoborohydride - Resin
• Trimethylammonium carbonate - Resin
• PHENYLTRIMETHYLSILANE
• Trimethoxypropylsilane
• (Trifluoromethyl)trimethylsilane
• Tms Acetylene