3989-15-9

Basic information

• Product Name: 2-TRIMETHYLSILYLETHYNYLTOLUENE
• Synonyms: 2-TRIMETHYLSILYLETHYNYLTOLUENE;trimethyl(o-tolylethynyl)silane;2-[(Trimethylsilyl)ethynyl]toluene 97%;Trimethyl-[2-(2-Methylphenyl)Ethynyl]Silane
• CAS NO: 3989-15-9
• Molecular Formula: C₁₂H₁₆Si
• Molecular Weight: 188.34
• Product Categories: Alkynes;Internal;Organic Building Blocks
• Mol File: 3989-15-9.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 50-60 °C0.5 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 0.880 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: n20/D 1.5320(lit.)
• Storage Temp.: below 5° C
• CAS DataBase Reference: 2-TRIMETHYLSILYLETHYNYLTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-TRIMETHYLSILYLETHYNYLTOLUENE(3989-15-9)
• EPA Substance Registry System: 2-TRIMETHYLSILYLETHYNYLTOLUENE(3989-15-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 3989-15-9(Hazardous Substances Data)

Usage

General Description

2-Trimethylsilylethynyltoluene is a chemical compound with the molecular formula C13H18Si. It is a derivative of toluene and contains a trimethylsilyl group and an ethynyl group. 2-TRIMETHYLSILYLETHYNYLTOLUENE is commonly used as a building block in organic synthesis and is known for its ability to undergo Sonogashira cross-coupling reactions to form new carbon-carbon bonds. Additionally, 2-trimethylsilylethynyltoluene has been investigated for its potential use in semiconductor applications due to its electron-donating properties and its ability to form stable films on various substrates. Overall, this compound is versatile and has a range of potential applications in organic synthesis and materials science.

InChI:InChI=1/C12H16Si/c1-11-7-5-6-8-12(11)9-10-13(2,3)4/h5-8H,1-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 766-47-2 1-ethynyl-2-methylbenzene 
• 1066-54-2 trimethylsilylacetylene 
• 95-46-5 2-methylphenyl bromide 
• 615-37-2 ortho-methylphenyl iodide 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 

Downstream Products

• 14309-60-5 1-phenylethynyltoluene 
• 1378520-32-1 1-methyl-2-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 503310-09-6 2,6-bis(2-methylphenyl)thiapyran-4-one 
• 503310-00-7 1,5-bis-(2-methylphenyl)-1,4-pentadiyn-3-one 
• 503309-91-9 bis-1,5-(2-methylphenyl)-1,4-pentadiyn-3-ol 
• 503309-96-4 1-(1,1-dimethylethyl)-5-(2-methylphenyl)-1,4-pentadiyn-3-one 
• 503309-89-5 1-(1,1-dimethylethyl)-5-(2-methylphenyl)-1,4-pentadiyn-3-ol 
• 503309-97-5 2-(1,1-dimethylethyl)-6-(2-methylphenyl)thiapyran-4-one 
• 521305-63-5 3-(ortho-tolyl)propiolaldehyde 
• 259090-89-6 (Z)-2,2‘-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) 

Relevant articles and documents

Naturally occurring 5-[2-thienyl)ethynyl]thiophene-2-carbaldehyde through a short synthesis of diarylacetylenes

Title compound and related diarylacetylenes were synthesized via a one-pot procedure starting from aryliodide and trimethylsilylacetylene.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes

Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.