87290-97-9

Basic information

• Product Name: PHENYLETHYNYLDIMETHYLSILANE
• Synonyms: DIMETHYL(PHENYLETHYNYL)SILANE;1-(DIMETHYLSILYL)-2-PHENYLACETYLENE;PHENYLETHYNYLDIMETHYLSILANE;Ethynyldimethylphenylsilane;Ethynylphenyldimethylsilane;Phenyldimethyl(ethynyl)silane;[(Dimethylsilyl)ethynyl]benzene
• CAS NO: 87290-97-9
• Molecular Formula: C₁₀H₁₂Si
• Molecular Weight: 160.29
• Mol File: 87290-97-9.mol

Chemical Properties

• Melting Point: <20°C
• Boiling Point: 33-34 °C0.33 mm Hg(lit.)
• Flash Point: 170 °F
• Appearance: /
• Density: 0.906 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.444mmHg at 25°C
• Refractive Index: n20/D 1.544(lit.)
• CAS DataBase Reference: PHENYLETHYNYLDIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLETHYNYLDIMETHYLSILANE(87290-97-9)
• EPA Substance Registry System: PHENYLETHYNYLDIMETHYLSILANE(87290-97-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 / PGIII
• WGK Germany: 3
• F: 10-21
• TSCA: No
• Hazardous Substances Data: 87290-97-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenylethynyldimethylsilane is utilized as a reagent in organic synthesis, specifically for the formation of carbon-silicon bonds. Its ability to engage in various reactions makes it a valuable component in creating complex organic structures.
Used in Silicon-based Material Production:
Phenylethynyldimethylsilane is also employed in the production of silicon-based materials, where its reactivity and bonding capabilities are crucial for developing new materials with unique properties.
Used as a Precursor for Organosilicon Compounds:
Phenylethynyldimethylsilane serves as a precursor for the synthesis of various organosilicon compounds, which have a wide range of applications in different industries due to their distinct chemical and physical properties.
Used in Chemical Research:
Due to its unique reactivity and potential applications, Phenylethynyldimethylsilane is an important compound in chemical research, where it can be used to explore new reaction pathways and develop innovative synthetic methods.

InChI:InChI=1/C10H12Si/c1-11(2)9-8-10-6-4-3-5-7-10/h3-7,11H,1-2H3

Upstream product

• 1066-35-9 dimethylmonochlorosilane 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 6738-06-3 phenylethynylmagnesium bromide 
• 113403-33-1 (1-methoxyethenyl)pentamethyldisilane 

Downstream Products

• 159015-72-2 dimethyl(2-phenylethynyl)silanol 
• 172228-59-0 1,1,3,3-tetramethyl-1,3-bis-phenylethynyl-disiloxane 
• 1219791-22-6 (C₅H₅)2Hf((CH₃)2HSiCCC₆H₅CC₆H₅CSi(CH₃)2H) 
• 1219791-23-7 (C₅H₅)2Hf((CH₃)2HSiCCC₆H₅CSi(CH₃)2HCC₆H₅) 
• 1234615-06-5 [μ-dimethyl[(1,2-η:1,2-η)-phenylethynyl]silane]bis[dicarbonyl(η5-cyclopentadienyl)molybdenum(I)] 
• 1333-74-0 hydrogen 
• 87710-79-0 methoxy-dimethyl(phenylethynyl)silane 

Relevant articles and documents

Catalytic Enantioselective Conjugate Addition of Stereodefined Di- and Trisubstituted Alkenylaluminum Compounds to Acyclic Enones

Catalytic enantioselective conjugate addition (ECA) reactions with readily accessible and stereochemically defined E-, Z-, di- and trisubstituted alkenyl aluminum compounds are disclosed. Transformations are promoted by various NHC-copper catalysts (NHC=N-heterocyclic carbene), which are derived from enantiomerically pure sulfonate imidazolinium salts. The desired products were obtained in up to 89% yield and >99:1 e.r.; the alkenyl moiety was transferred with complete retention of its stereochemical identity in all instances. The scope and limitations of the approach, key mechanistic attributes, and representative functionalization are presented as well. (Figure presented.).

Selective Manganese-Catalyzed Oxidation of Hydrosilanes to Silanols under Neutral Reaction Conditions

The first manganese-catalyzed oxidation of organosilanes to silanols with H2O2 under neutral reaction conditions has been accomplished. A variety of organosilanes with alkyl, aryl, alknyl, and heterocyclic substituents were tolerated, as well as sterically hindered organosilanes. The oxidation appears to proceed by a concerted process involving a manganese hydroperoxide species. Featuring mild reaction conditions, fast oxidation, and no waste byproducts, the protocol allows a low-cost, eco-benign synthesis of both silanols and silanediols.

METHOD FOR PRODUCING ORGANOSILICON COMPOUND USING HALOSILANE AS RAW MATERIAL

PROBLEM TO BE SOLVED: To provide a novel method for producing an organosilicon compound. SOLUTION: The method for producing an organosilicon compound includes a reaction step (I) of reacting a halosilane represented by formula (a) with a compound containing a hydrocarbon group represented by formula (b) in the presence of an organic base to generate an organosilicon compound represented by formula (c). (In the formula (I), n is an integer of 0-3; each R1 independently represents a hydrogen atom or a C1-20 hydrocarbon group which may contain a heteroatom; X represents a bromo group (-Br) or a chloro group (-Cl); and R2 represents a compound containing a hydrocarbon group.) SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

Sterically directed iridium-catalyzed hydrosilylation of alkenes in the presence of alkynes

A selective iridium catalyzed hydrosilylation of alkenes in the presence of more reactive alkynes is described. By utilizing [IrCl(COD)]2 in the presence of excess COD, hydrosilylation of alkenes and alkynes with ethynylsilanes is achieved with

Selective synthesis of functional alkynylmono- and -trisilanes

The selective synthesis of functional alkynylsllanes RC=C(SiMe 2)m,-X (m = 1, 3) was investigated. Monofunctionalization with or without protecting groups gave moderate to good yields of alkynyldimethylmonosilanes RC=CMe2SiX [R = Ph, X = Cl. (1), NEt 2 (2), OMe (3), H (4), Br (5), I (6), Cp (8), C5H 4Li (10), Ph (11); R = Pr, X = Ph (12)]. Compounds 4 and 8 were converted into the (alkyne)transition-metal complexes 4-Cp2Mo 2(CO)4 (13) and 8-Co2(CO)6 (14), respectively, which were characterized by X-ray diffraction. Stepwise extension and functionalization of the silane chain starting from 1chloro-2-(diethylamino) tetramethyldisilane (Et2NMe2Si-SiMe2Cl) yielded the trisilanes Ph-(SiMe2J3-X [X = NEt2 (18), OMe (19), Cl (20), H (21), C=CPh (22), C=CPr (23)]. The synthesized compounds were characterized by NMR and IR spectroscopy, 4, 11, 13, and 14 also by UV/Vis spectroscopy.

Preparation of novel photoluminescent oligocarbosilanes by hydrosilylation [4]

The preparation of the photoluminescent oligocarbosilanes by hydrosilylation was discussed. Karstedt-catalyzed oligomerization of photoluminescent oligocarbosilanes was carried out in an argon atmosphere in a sealed pressure tube. The initially colorless monomer became dark brown within one minute after addition of catalysts. The photoluminescent polymers offer flexibilities in molecular design and good processability. Their luminescent properties could be tuned at the molecular level. The photoluminescent oligocarbosilanes are unique because they contain both conjugated and cross conjugated segments.

Synthesis of some mono- and diethynylsilanes

Alkynylsilanes of the general formula MenSiH(C≡CR)3-n (R = SiMe3, Ph; n = 1, 2) have been synthesized by reaction of chlorodimethylsilane and dichloromethylsilane with Iotsitch reagents derived from phenylacetylene and eth