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Hexakis-[(trimethylsilyl)ethynyl]benzene, with the chemical formula C36H30Si6, is a sixfold silylated derivative of hexaethynylbenzene. In this compound, each of the six hydrogen atoms in the benzene ring is substituted by a trimethylsilyl group. It exists as a crystalline solid with a high melting point and is known for its unique electronic and optical properties. These characteristics make it a promising candidate for applications in materials science and organic electronics.

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  • Silane, (1,2,3,4,5,6-benzenehexaylhexa-2,1-ethynediyl)hexakis[trimethyl-

    Cas No: 100516-62-9

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  • 100516-62-9 Structure
  • Basic information

    1. Product Name: hexakis-[(trimethylsilyl)ethynyl]benzene
    2. Synonyms: hexakis-[(trimethylsilyl)ethynyl]benzene;hexakis-[(trimethylsilyl)ethynyl]ben
    3. CAS NO:100516-62-9
    4. Molecular Formula: C36H54Si6
    5. Molecular Weight: 655.32696
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 100516-62-9.mol
  • Chemical Properties

    1. Melting Point: 224.7 °C
    2. Boiling Point: 583.7±50.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 0.95±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: hexakis-[(trimethylsilyl)ethynyl]benzene(CAS DataBase Reference)
    10. NIST Chemistry Reference: hexakis-[(trimethylsilyl)ethynyl]benzene(100516-62-9)
    11. EPA Substance Registry System: hexakis-[(trimethylsilyl)ethynyl]benzene(100516-62-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 100516-62-9(Hazardous Substances Data)

100516-62-9 Usage

Uses

Used in Materials Science:
Hexakis-[(trimethylsilyl)ethynyl]benzene is utilized as a building block in the synthesis of functional organic materials. Its unique properties contribute to the development of advanced materials for various technological applications.
Used in Organic Electronics:
Due to its electronic and optical properties, hexakis-[(trimethylsilyl)ethynyl]benzene is employed in the creation of organic electronic devices, where it can enhance performance and contribute to the advancement of the field.

Check Digit Verification of cas no

The CAS Registry Mumber 100516-62-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,5,1 and 6 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100516-62:
(8*1)+(7*0)+(6*0)+(5*5)+(4*1)+(3*6)+(2*6)+(1*2)=69
69 % 10 = 9
So 100516-62-9 is a valid CAS Registry Number.

100516-62-9Relevant articles and documents

Deuteration effects on the vibronic structure of the fluorescence spectra and the internal conversion rates of triangular [4]phenylene

Dosche,Kumke,Loehmannsroeben,Ariese,Bader,Gooijer,Miljanic,Iwamoto,Vollhardt,Puchta,Van Eikema Hommes

, p. 5476 - 5483 (2004)

Deuteration effects on the vibronic structure of the emission and excitation spectra of triangular [4]phenylene (D3h [4]phenylene) were studied using laser-excited Shpol'skii spectroscopy (LESS) in an octane matrix at 4.2 K. For correct assignm

Intermolecular On-Surface σ-Bond Metathesis

Gao, Hong-Ying,Held, Philipp Alexander,Amirjalayer, Saeed,Liu, Lacheng,Timmer, Alexander,Schirmer, Birgitta,Díaz Arado, Oscar,M?nig, Harry,Mück-Lichtenfeld, Christian,Neugebauer, Johannes,Studer, Armido,Fuchs, Harald

, p. 7012 - 7019 (2017)

Silylation and desilylation are important functional group manipulations in solution-phase organic chemistry that are heavily used to protect/deprotect different functionalities. Herein, we disclose the first examples of the σ-bond metathesis of silylated alkynes with aromatic carboxylic acids on the Ag(111) and Au(111) surfaces to give the corresponding terminal alkynes and silyl esters, which is supported by density functional theory calculations and further confirmed by X-ray photoelectron spectroscopy analysis. Such a protecting group strategy applied to on-surface chemistry allows self-assembly structures to be generated from molecules that are inherently unstable in solution and in the solid state. This is shown by the successful formation of self-assembled hexaethynylbenzene at Ag(111). Furthermore, it is also shown that on the Au(111) surface this σ-bond metathesis can be combined with Glaser coupling to fabricate covalent polymers via a cascade process.

Hierarchical Co3(PO4)2/CuI/g-CnH2n–2 S-Scheme Heterojunction for Efficient Photocatalytic Hydrogen Evolution

Su, Peng,Liu, Hai,Jin, Zhiliang

, p. 19402 - 19413 (2021/12/17)

Graphdiyne (GD), a new type of carbon allotrope formed by sp and sp2 hybrid carbon atoms, has attracted wide attention due to its high π-conjugation degree, special band structure, and uniformly distributed pores. In traditional synthesis metho

Graphite diyne film and preparation method and application thereof

-

Paragraph 0042, (2021/09/04)

The invention relates to a graphite diyne film as well as a preparation method and application thereof. A precursor of the graphite diyne film is hexa(bromo-ethynyl) benzene. The method comprises the following steps: (1) injecting a solvent into a reactor filled with hexa(bromo-ethynyl) benzene and a copper-containing substrate; (2) dropwise adding an alkali solution into the reactor, stirring under the protection of an inert atmosphere, and carrying out a debromination coupling reaction; and (3) after the reaction is finished, generating a layer of black semitransparent film on the surface of the substrate, washing the surface of the substrate with acetone and N,N-dimethylformamide to obtain a black graphite diyne film which is applied to a catalytic material, an energy material or an electrode material. Compared with the prior art, the preparation method has the advantages that monomer molecules are more stable in air and higher in reaction activity, a coupling reaction can be stably and efficiently carried out, the reaction time is greatly shortened, the reaction can be carried out at room temperature, additional heating is not needed, energy can be greatly saved, and the problem of organic solvent volatilization caused by heating is solved.

Distinctive Improved Synthesis and Application Extensions Graphdiyne for Efficient Photocatalytic Hydrogen Evolution

Li, Yanbing,Yang, Hao,Wang, Guorong,Ma, Bingzhen,Jin, Zhiliang

, p. 1985 - 1995 (2020/02/13)

Graphdiyne (GD), a novel two-dimension carbon hybrid material, due to its unique and excellent properties, has been widely concerned since this innovative material was successfully synthesized by Prof. Yuliang Li in 2010. Traditionally, its synthesis method is growing graphdiyne on copper foils or foam copper as a base catalytic material to deliver copper ions (Cu2+) under pyridine conditions. Here, an innovative progress for graphdiyne preparation approach of using Cu+ ion as a catalytic material is reported and its application in extending to the photocatalytic water-splitting to produce hydrogen in situ as well. In detail, by means of cuprous iodide used as a catalyst-carrier to grow a graphdiyne in a pyridine solution of monomeric hexynylbenzene and such CuI-graphdiyne composite catalyst is directly applied to photocatalytic hydrogen production in situ. Meanwhile, the hydrogen production of GD and CuI are 29.42 μmol/5 h and 156.49 μmol/5 h, respectively. In particular, the composite catalyst GD-CuI exhibits an optimum photo-catalytic hydrogen production activity (465.95 μmol/5 h) which is 15.8 times and 3.0 times that of pure GD and CuI respectively. This rational design, one-step construction of GD-CuI, successfully enhances photo-catalytic hydrogen evolution activity. The deeper characterization study results such as TEM, SEM, XPS, XRD, UV-vis DRS, Transient photocurrent and FT-IR etc. have been well researched and the results of which are in good agreement with each other.

Engineering the Coordination Environment of Single-Atom Platinum Anchored on Graphdiyne for Optimizing Electrocatalytic Hydrogen Evolution

Yin, Xue-Peng,Wang, Hong-Juan,Tang, Shang-Feng,Lu, Xiu-Li,Shu, Miao,Si, Rui,Lu, Tong-Bu

supporting information, p. 9382 - 9386 (2018/07/29)

Two Pt single-atom catalysts (SACs) of Pt-GDY1 and Pt-GDY2 were prepared on graphdiyne (GDY)supports. The isolated Pt atoms are dispersed on GDY through the coordination interactions between Pt atoms and alkynyl C atoms in GDY, with the formation of five-

PROCESSES FOR PRODUCING POLY-ETHYNYL-SUBSTITUTED AROMATIC COMPOUND

-

Page column 8, (2010/02/05)

A process for preparing a poly-ethynyl-substituted aromatic compound characterized by reacting a halogenated benzene with an ethynylzinc halide; a process for preparing a poly-ethynyl-substituted aromatic compound characterized by using a halogenated benzene having at least two kinds of halogen atoms as a halogenated benzene, and (A) reacting one kind of the halogen atoms existing in the halogenated benzene with an ethynyl group-containing compound; and (B) reacting the other kind of halogen atoms remaining in the formed compound with an ethynylzinc halide. The poly-ethynyl-substituted aromatic compound is used as liquid crystals, nonlinear optical materials, electroconductive materials and the like

Synthesis of differentially substituted hexaethynylbenzenes based on tandem sonogashira and Negishi cross-coupling reactions

Sonoda, Motohiro,Inaba, Akiko,Itahashi, Kayo,Tobe, Yoshito

, p. 2419 - 2421 (2007/10/03)

(matrix presented) Synthesis of polyethynyl-substituted aromatic compounds was achieved efficiently by the use of the Negishi cross-coupling reaction, and this method, coupled with the Sonogashira reaction, was applied to the synthesis of differentially s

Synthesis of High Carbon Materials from Acetylenic Precursors. Preparation of Aromatic Monomers Bearing Multiple Ethynyl Groups

Neenan, Thomas X.,Whitesides, George M.

, p. 2489 - 2496 (2007/10/02)

The synthesis of polyethynyl aromatics as starting materials for the preparation of highly cross-linked organic solids containing high atom fractions of carbon is described.Treatment of bromo- and iodoaromatic compounds with (trimethylsilyl)acetylene (TMSA) in the presence of palladium(O) and copper(I) in amine solvents yields (trimethylsilyl)ethynyl-substituted aromatics.The TMS protecting groups can be removed by hydrolysis with mild base.Compounds prepared by using this technique include 1,3-diethynylbenzene, 2,5-diethynylthiophene, 1,3-diethynyltetrafluorobenzene, 1,4-diethynyltetrafluorobenzene, 2-ethynylthiazole, 2,4-diethynylthiazole, 2,7-diethynylnaphthalene, hexakis((trimethylsilyl)ethynyl)benzene, tetraethynylthiophene, 2,5-bis((trimethylsilyl)ethynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-diethynyl-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-bis(4-(2-thienyl)butadiynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, and 2,5-bis-(4-(2-thienyl)butadiynyl)-3,4-diethynylthiophene.

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