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HomeProduct name listTrimethylsilylacetylene

Trimethylsilylacetylene

Synonym(s):Ethinyltrimethylsilane;Trimethylsilylacetylene

  • CAS NO.:1066-54-2
  • Empirical Formula: C5H10Si
  • Molecular Weight: 98.22
  • MDL number: MFCD00008569
  • EINECS: 213-919-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Trimethylsilylacetylene Structural

What is Trimethylsilylacetylene?

Chemical properties

CLEAR COLORLESS LIQUID

Physical properties

bp 53 °C; d 0.695 g cm?3.

The Uses of Trimethylsilylacetylene

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.

The Uses of Trimethylsilylacetylene

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

The Uses of Trimethylsilylacetylene

(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.

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.]

Properties of Trimethylsilylacetylene

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
color  colorless
Specific Gravity 0.695
Water Solubility  reacts
Hydrolytic Sensitivity 4: no reaction with water under neutral conditions
BRN  906752
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 for Trimethylsilylacetylene

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P241:Use explosion-proof electrical/ventilating/lighting/…/equipment.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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 Trimethylsilylacetylene

InChIKey CWMFRHBXRUITQE-UHFFFAOYSA-N

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