2170-06-1

Basic information

• Product Name: 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE
• Synonyms: 1-Phenyl-2-trimethylsilylacetylene,1-(Trimethylsilyl)-2-phenylacetylene, Phenylethynyl-trimethylsilane, Trimethyl(phenylethynyl)silane;1-PHENYL-2-TRIMETHYLSILYLACETYLENE 99%;2-Phenyl-1-(trimethylsilyl)acetylene;2-Phenyl-1-ethynyltrimethylsilane;Phenyl(trimethylsilyl)ethyne;Benzene, [2-(trimethylsilyl)ethynyl]-;Silane, trimethyl(phenylethynyl);[2-(Trimethylsilyl)ethynyl]benzene
• CAS NO: 2170-06-1
• Molecular Formula: C₁₁H₁₄Si
• Molecular Weight: 174.31
• Product Categories: Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds
• Mol File: 2170-06-1.mol

Chemical Properties

• Boiling Point: 87-88 °C9 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: Colorless/Liquid
• Density: 0.886 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: 2-8°C
• Solubility: Sparingly Soluble (6.1E-3 g/L) (25°C)
• BRN: 3088678
• CAS DataBase Reference: 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE(2170-06-1)
• EPA Substance Registry System: 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE(2170-06-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• F: 8
• TSCA: No
• Hazardous Substances Data: 2170-06-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Phenyl-2-(trimethylsilyl)acetylene is used as a key building block in the synthesis of various complex organic molecules. Its unique reactivity allows for the formation of new carbon-carbon and carbon-silicon bonds, which are essential in the creation of a wide range of compounds.
Used in the Preparation of Donor-Stabilized Pt-η2-alkyne Complexes:
1-Phenyl-2-(trimethylsilyl)acetylene is used as a precursor in the preparation of donor-stabilized Pt-η2-alkyne complexes. These complexes have potential applications in homogeneous catalysis, where they can act as catalysts for various chemical reactions, including olefin polymerization and cross-coupling reactions.
Used in Polymer Science:
In the field of polymer science, 1-Phenyl-2-(trimethylsilyl)acetylene is used as a monomer for the synthesis of novel polymers with unique properties. The polymerization process, facilitated by transition metal catalysts, allows for the creation of polymers with tailored characteristics, such as improved thermal stability, mechanical strength, and chemical resistance.
Used in the Electronics Industry:
1-Phenyl-2-(trimethylsilyl)acetylene and its derivatives can be used in the development of advanced materials for the electronics industry. These materials may find applications in the fabrication of semiconductors, optoelectronic devices, and sensors, due to their unique electronic and optical properties.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1-Phenyl-2-(trimethylsilyl)acetylene and its derivatives may also have potential applications in the pharmaceutical industry. The unique structural features of this compound can be exploited for the design and synthesis of new drugs with improved pharmacological properties, such as enhanced bioavailability, selectivity, and reduced side effects.

InChI:InChI=1/C11H14Si/c1-12(2,3)10-9-11-7-5-4-6-8-11/h4-8H,1-3H3

Upstream product

• 109-72-8 n-butyllithium 
• 536-74-3 phenylacetylene 
• 925-90-6 ethylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 18163-47-8 iodoethynyltrimethylsilane 
• 3220-49-3 phenyl copper 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 6738-06-3 phenylethynylmagnesium bromide 
• 67-56-1 methanol 
• 81142-36-1 1-phenylethynyl-1-phenyltetramethyldisilane 
• 81142-37-2 1-phenylethynyl-1,1-diphenyltrimethyldisilane 
• 1122-79-8 potassium phenylacetylide 
• 591-50-4 iodobenzene 

Downstream Products

• 1817-57-8 4-phenyl-3-butyne-2-one 
• 6181-26-6 1-trichloromethyl-3-phenyl-2-propyn-1-ol 
• 52137-73-2 Trimethyl-(3-phenyl-1-trichloromethyl-prop-2-ynyloxy)-silane 
• 176648-09-2 1-chloro-4-phenyl-3-butyn-2-one 
• 18052-61-4 1,4-Dichlor-2-trimethylsilyl-1-phenyl-buten-⁽¹⁾-on-⁽³⁾ 
• 16124-02-0 7-Trimethylsilyl-8-phenyl-bicyclo<4.4.2>deca-2,4,7,9-tetraen 
• 70639-92-8 1-(1-methylcyclopentyl)-3-phenylprop-2-yn-1-one 
• 18754-65-9 3,5-Diphenyl-2,4-bis-trimethylsilyl-cyclopentadienon 
• 18754-38-6 3,4-diphenyl-2,5-bis-trimethylsilanyl-cyclopenta-2,4-dienone 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 19319-11-0 (Z)-1-phenyl-2-(trimethylsilyl)ethylene 
• 78133-25-2 (Z)-β-Deuterio-β-styryl(trimethyl)silan 
• 109-09-1 2-chloropyridine 
• 13141-42-9 2-(2-phenylethynyl)pyridine 

Relevant articles and documents

Reactions of in situ generated (η2-phenyltrimethylsilylacetylene)zirconocene

The five-membered metallacycle (1, R1 = SiMe3, R2 = Ph) is a suitable starting material for the in situ generation of the reactive (η2-phenyltrimethylsilylethyne)zirconocene (3).Thus, thermolysis of 1 (70 deg C) with trimethylphosphane gives Cp2Zr(Me3SiCCPh)(PMe3) (8) and free Me3SiCCPh (4).Subsequent reaction of 8 with acetophenone produces (9, R1 = SiMe3, R2 = Ph).Thermolysis of 1 in the presence of CpW(CO)3H also results in the liberation of one equivalent of 4.The reactive intermediate 3 is protonated to giveCp2Zr(CR1=CHR2)(μ-OC)W(CO)2Cp (12, R1 = SiMe3, R2 = Ph).Treatment of 1 with in acetonitrile gives the cationic (13a: R1 = SiMe3, R2 = Ph) and its regioisomer 13b (R1 and R2 exchanged).There is evidence that the complexes 13 are formed by acetonitrile addition to thermally-generated 3 to give , which is then subsequently protonated at the basic ring nitrogen.These reactions show that a readily available metallacyclopentadiene system can be used as a convenient synthetic equivalent of a very reactive (η2-alkyne)metallocene complex by thermally induced equilibration in the presence of suitable trapping reagents.

Effect of the Grignard reagent on the X→Csp, migration of the MR3 group in HC ≡ CCH2XMR3 compounds

The effect of the Grignard compounds (EtMgBr, PhMgBr, t-BuMgCl, cyclo-C6H11MgBr, and PhC≡CMgBr) on the isomerization of HC≡CCH2XMR3 into R3MC≡CCH2XH (M = Si, Ge; X = O, S) was studied. The efficiency of the 1,4-(X→Csp)-migration of the R3M group was shown to depend on the nucleophilicity of the Grignard compound and nature of the M-X bond.

Dimetallation of Phenylacetylene. Selective ortho-Substitution

Reaction of lithium phenylacetylide with the complex BuLi-ButOK in a mixture of tetrahydrofuran and hexane leads to the ortho-metallated phenylacetylide; subsequent addition of methyl iodide, dimethyl disulphide, trimethylchlorosilane, and sele

Bimetallic nano-Pd/PdO/Cu system as a highly effective catalyst for the Sonogashira reaction

A copper-supported nanopalladium catalyst obtained by an innovative method of nanoparticle transfer from the intermediate carrier SiO2 to the target Cu carrier was a highly efficient and selective catalyst, giving as much as quantitative conver

Decarboxylative Alkynyl Termination of Palladium-Catalyzed Catellani Reaction: A Facile Synthesis of α-Alkynyl Anilines via Ortho C - H Amination and Alkynylation

A palladium-catalyzed synthesis of α-alkynyl anilines is reported. The reaction proceeds via Catellani ortho C-H amination followed by decarboxylative alkynylative amination. Different terminal alkyne precursors were screened, and it was found that alkyny

A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.

Thermolysis of 1,1-dimesityl-3-phenyl-2-trimethylsilyl-1-silacyclopropene: Silylene transfer reactions to 1,4-bis(silyl)butadiynes

The cothermolysis of 1,1-dimesityl-3-phenyl-2-trimethylsilyl-1-silacyclopropene (1) with 1,4-bis(triethylsilyl)- and 1,4-bis(triethylsilyl)butadiyne at 250°C for 24 h afforded 1,1-dimesityl-3-silyl-2-silylethynyl-1-silacyclopropenes (3 and 5) and dimesitylbis(silylethynyl)silanes (4 and 6), respectively. The thermolysis of silacyclopropene 3 under the same conditions cleanly produced an isomerization product 4.

Formation and ligand-based reductive chemistry of bridged bis-alkylidene scandium(III) complexes

The chemistry of rare-earth carbene and alkylidene complexes including their synthesis, structure and reaction is a challenging issue because of their high reactivity (or instability) and the lack of synthetic methods. In this work, we report the first synthesis of the bridged bis-alkylidene complexes which feature a 2-butene-1,1,4,4-tetraanion and four Sc-C(sp3) bonds by the reaction of 1,4-dilithio-1,3-butadienes with ScCl3. This reaction proceeds via two key intermediates: an isolable scandacyclopentadiene and a proposed scandacyclopropene. The scandacyclopentadiene undergoes β,β′-C-C bond cleavage to generate the scandacyclopropene, which then dimerizes to afford the bridged bis-alkylidene complex via a cooperative double metathesis reaction. Reaction chemistry study of the bridged bis-alkylidene complex reveals their ligand-based reduction reactivity towards different oxidants such as hexachloroethane, disulfide and cyclooctatetraene.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

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.