17938-13-5

Basic information

• Product Name: 1,4-Bis[(trimethylsilyl)ethynyl]benzene
• Synonyms: TIMTEC-BB SBB009009;1,4-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE;1,4-BIS((TRIMETHYLSILYL)ETHYNYL)BENZENE 98%;1,4-Bis(trimethylsilyl)ethynylübenzene, 98%;1,4-Bis[(trimethylsilyl)ethynyl]benzene,98%;1,4-Bis(trimethylsilyl)ethynylubenzene;1,4-bis[2-(trimethylsilyl)ethynyl]Benzene
• CAS NO: 17938-13-5
• Molecular Formula: C₁₆H₂₂Si₂
• Molecular Weight: 270.52
• EINECS: -0
• Product Categories: Alkynes;Internal;Organic Building Blocks
• Mol File: 17938-13-5.mol
• Article Data: 58

Chemical Properties

• Melting Point: 119 °C
• Boiling Point: 292.1°C at 760mmHg
• Flash Point: 112.2°C
• Appearance: White crystalline powder
• Density: 0.92g/cm³
• Vapor Pressure: 0.00327mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: Refrigerator (+4°C)
• BRN: 2840618
• CAS DataBase Reference: 1,4-Bis[(trimethylsilyl)ethynyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis[(trimethylsilyl)ethynyl]benzene(17938-13-5)
• EPA Substance Registry System: 1,4-Bis[(trimethylsilyl)ethynyl]benzene(17938-13-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 17938-13-5(Hazardous Substances Data)

Usage

Description

1,4-Bis[(trimethylsilyl)ethynyl]benzene is a diyne compound characterized by its white crystalline powder appearance. It can be synthesized through the reduction of 1,4-bis[(trimethylsilyl)ethynyl]-2,5-cyclohexadiene-1,4-diol using stannous chloride. 1,4-Bis[(trimethylsilyl)ethynyl]benzene is notable for its reactivity, as it readily undergoes hydroalumination with di(tert-butyl)aluminium hydride, resulting in the addition of one Al-H bond to each C-C triple bond.

Uses

Used in Chemical Synthesis:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is used as a key intermediate in the synthesis of various organic compounds. Its unique reactivity allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Material Science:
In the field of material science, 1,4-Bis[(trimethylsilyl)ethynyl]benzene is utilized as a precursor for the development of advanced materials with specific properties. Its ability to form stable bonds with other elements makes it a valuable component in the design of new materials with tailored characteristics.
Used in Pharmaceutical Research:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is employed as a building block in the design and synthesis of novel pharmaceutical compounds. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Electronics Industry:
In the electronics industry, 1,4-Bis[(trimethylsilyl)ethynyl]benzene is used as a component in the development of advanced electronic materials, such as semiconductors and conductive polymers. Its electronic properties make it a promising candidate for enhancing the performance of electronic devices.
Used in Nanotechnology:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is utilized in nanotechnology for the fabrication of nanoscale structures and devices. Its ability to form stable bonds with other elements allows for the precise manipulation of materials at the nanoscale, leading to the development of innovative applications in various fields.

InChI:InChI=1/C16H22Si2/c1-17(2,3)13-11-15-7-9-16(10-8-15)12-14-18(4,5)6/h7-10H,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 624-38-4 para-diiodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 935-14-8 1,4-diethynylbenzene 
• 106-37-6 1.4-dibromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 544706-67-4 cis-1,4-diacetoxy-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 862801-08-9 1,4-bis[(trimethylsilyl)ethynyl]-2,5-cyclohexadiene-1,4-diol 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 935-14-8 1,4-diethynylbenzene 
• 168762-34-3 1,4-bis(4',4'-dichloro-2'-trimethylsilyl-3'-oxo-1'cyclobutenyl)benzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 147492-76-0 1-(phenylethynyl)-4-[(trimethylsilyl)ethynyl]benzene 
• 475094-86-1 1,4-bis-[(dimethoxy-methyl-silanyl)-ethynyl]-benzene 
• 79109-90-3 1,4-bis-1,3-butadiyne 
• 66228-76-0 4-(trimethylsilylethynyl)phenylacetylene 
• 866825-55-0 4-[2-(4-ethynylphenyl)ethynyl]benzoic acid 
• 596093-52-6 [benzene-1,4-bis(2,1-ethynedyil)]bis[3-(4-ethynylpyridine)] 
• 596093-50-4 [benzene-1,4-bis(2,1-ethynedyil)]bis[3-(4-trimethylsilylethynylpyridine)] 
• 885065-48-5 1,4-bis(4-isocyanatophenylethynyl)benzene 
• 546112-60-1 N-{4-[4-(4-formylaminophenylethynyl)phenylethynyl]phenyl}formamide 
• 421554-44-1 1,4-bis(2-(4-iodophenyl)ethyl)benzene 

Relevant articles and documents

Pyrazine-based donor tectons: Synthesis, self-assembly and characterization

Two new supramolecular building blocks derived from pyrazine are introduced. These molecules, having pendant pyridine units covalently linked to central pyrazine ring, are structurally rigid with pre-defined bite angles. Therefore they can act as donor tectons in design of supramolecular hexagons using coordination driven self-assembly protocol. Multinuclear NMR (including 1H DOSY) and mass spectrometry have been utilized to confirm the purity and stoichiometry of these self assembled hexagonal ensembles. PM6 molecular modeling studies corroborate their hexagonal shape and nanoscalar dimensions.

A Triazine-Based Analogue of Graphyne: Scalable Synthesis and Applications in Photocatalytic Dye Degradation and Bacterial Inactivation

Graphyne, a theorized carbon allotrope possessing only sp- and sp2-hybridized carbon atoms, holds great potentials in many fields, especially in catalysis and energy-transfer/storage devices. Using a bottom-up strategy, we synthesized a new N-doped graphyne analogue, triazine- and 1,4-diethynylbenzene-based graphyne TA-BGY, in solution in gram-scale. The unique sp/sp2 carbon-conjugated TA-BGY possesses an extended porous network structure with a BET surface area of approximately 300 m2 g?1. Owing to its low optical band gap (1.44 eV), TA-BGY was expected to have many applications, which were exemplified by the photodegradation of methyl orange and photocatalytic bacterial inactivation.

Structurally-Defined, Sulfo-Phenylated, Oligophenylenes and Polyphenylenes

We report the synthesis and molecular characterization of structurally defined, sulfo-phenylated, oligo- and polyphenylenes that incorporate a novel tetra-sulfonic acid bistetracyclone monomer. The utility of this monomer in the [4 + 2] Diels-Alder cycloaddition to produce well-defined, sulfonated oligophenylenes and pre-functionalized polyphenylene homopolymers is demonstrated. Characterization of the oligophenylenes indicates formation of the meta-meta and para-para adducts in a ～ 1:1 ratio. These functionalized monomers and their subsequent coupling provide a route to prepare novel, sterically encumbered, sulfonated polyphenylenes possessing unprecedented structural control.

C-Au Covalently Bonded Molecular Junctions Using Nonprotected Alkynyl Anchoring Groups

We report on an approach to realize carbon-gold (C-Au) bonded molecular junctions without the need for an additive to deprotect the alkynyl carbon as endstanding anchor group. Using the mechanically controlled break junction (MCBJ) technique, we determine the most probable conductance value of a family of alkynyl terminated oligophenylenes (OPA(n)) connected to gold electrodes through such an akynyl moiety in ambient conditions. The molecules bind to the gold leads through an sp-hybridized carbon atom at each side. Comparing our results with other families of molecules that present organometallic C-Au bonds, we conclude that the conductance of molecules contacted via an sp-hybridized carbon atom is lower than the ones using sp3 hybridization due to strong differences in the coupling of the conducting orbitals with the gold leads.

Synthesis of Rigid Rod, Trigonal, and Tetrahedral Nucleobase-Terminated Molecules

An efficient fragment splicing method for the construction of multiple nucleobase-terminated monomers has been developed. Conformationally fixed rod, trigonal planar and tetrahedral thymine and adenine structures were generated in moderate to good yields,

Catalytic Decarboxylation of Silyl Alkynoates to Alkynylsilanes

Herein, we describe a decarboxylative approach to the preparation of alkynylsilanes. Treatment of a silyl alkynoate in N,N-dimethylformamide (DMF) at 80 °C in the presence of catalytic amounts of CuCl and PCy3 produced the corresponding alkynylsilane in excellent yield. The copper-catalyzed decarboxylation proceeded smoothly with low catalyst loadings (0.5 mol % of CuCl and 1.0 mol % of PCy3) under mild reaction conditions and is easily scalable to gram quantities.