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

Chemical Properties

White crystalline powder

General Description

1,4-Bis[(trimethylsilyl)ethynyl]benzene is a diyne that can be prepared by the reduction of 1,4-bis[(trimethylsilyl)ethynyl]-2,5-cyclohexadiene-1,4-diol with stannous chloride. It reacts with di(tert-butyl)aluminium hydride by hydroalumination and undergoes addition of one Al-H bond to each C-C triple bond.

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

Downstream Products

• 168762-34-3 1,4-bis(4',4'-dichloro-2'-trimethylsilyl-3'-oxo-1'cyclobutenyl)benzene 
• 475094-86-1 1,4-bis-[(dimethoxy-methyl-silanyl)-ethynyl]-benzene 
• 935-14-8 1,4-diethynylbenzene 
• 1004265-66-0 α,α'-diiodo-1,4-divinylbenzene 
• 130778-59-5 1,4-bis(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 113509-26-5 1,4-bis<2-(trimethylsilyl)ethenyl>benzene 
• 7608-33-5 1,4-bis[(diphenylphosphino)ethynyl]benzene 
• 1431043-06-9 1,4-bis((5-methylthiophen-2-yl)ethynyl)benzene 
• 308103-23-3 s-trans-[E,E]-1,4-bis(2-di(tert-butyl)aluminium-2-trimethylsilyl-ethenyl)benzene 
• 1318759-19-1 [Ru(CCC₆H₄CCSi(CH₃)3)(1,2-bis(diphenylphosphino)ethane)(C₅(CH₃)5)] 

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,

Microwave-assisted unprotected Sonogashira reaction in water for the synthesis of polysubstituted aromatic acetylene compounds

A microwave-assisted, efficient and rapid Sonogashira reaction was developed for the synthesis of polysubstituted aromatic alkynes. The reaction was made environmentally friendly and easy to perform by replacing the traditional amine solvents with water.