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

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

Downstream Products

• 110598-37-3 4-((Z)-1-o-Tolyl-2-trimethylsilanyl-vinyl)-phenol 
• 7517-82-0 methyl 3-(2-methylphenyl)-2-propynoate 
• 5294-03-1 di-o-tolylethyne 
• 1369558-70-2 isobutyl 5-(2-methylphenyl)-4-pentynoate 
• 1369558-69-9 n-butyl 5-(2-methylphenyl)-4-pentynoate 
• 1369558-75-7 5-(2-methylphenyl)-pent-4-ynoic acid 6-(5-(2-methylphenyl)-pent-4-ynoyloxy)-hexyl ester 
• 1369558-68-8 methyl 5-(2-methylphenyl)-4-pentynoate 
• 1369558-64-4 ethyl 5-(2-methylphenyl)-4-pentynoate 
• 1378520-32-1 1-methyl-2-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 1268338-86-8 1-(4-fluorophenyl)-2,5-dimethyl-4-o-tolylethynyl-1H-imidazole 
• 136053-56-0 1,4-di-(o-tolyl)buta-1,3-diyne 
• 503310-09-6 2,6-bis(2-methylphenyl)thiapyran-4-one 
• 503310-00-7 1,5-bis-(2-methylphenyl)-1,4-pentadiyn-3-one 

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.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea