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
• Article Data: 8

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

General Description

Phenylethynyldimethylsilane is a chemical compound with the molecular formula C10H12Si. It is a colorless liquid that is used as a reagent in organic synthesis, particularly in the formation of carbon-silicon bonds. Phenylethynyldimethylsilane is also used in the production of silicon-based materials and as a precursor for various organosilicon compounds. It is highly reactive and can undergo a variety of reactions, including addition, elimination, and substitution reactions. Due to its versatile reactivity and potential applications, phenylethynyldimethylsilane is an important compound in the field of organic and materials chemistry.

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 
• 6738-06-3 phenylethynylmagnesium bromide 
• 4440-01-1 lithium phenylacetylide 
• 113403-33-1 (1-methoxyethenyl)pentamethyldisilane 

Downstream Products

• 122627-07-0 (dicobalt)(carbonyl)6(dimethyl(phenylethynyl)silane) 
• 918546-09-5 (C₆H₅)(CH₂CHCH₂)CC(SiH(CH₃)2)(B(CH₂CHCH₂)2) 
• 159015-72-2 dimethyl(2-phenylethynyl)silanol 
• 172228-59-0 1,1,3,3-tetramethyl-1,3-bis-phenylethynyl-disiloxane 
• 1367364-02-0 chlorohydrido[dimethyl(phenylethynyl)silyl]bis(triphenylphosphane)rhodium(III) 
• 1333-74-0 hydrogen 

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.).

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

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.