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1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE, also known as TES-protected diyne, is a symmetrical diacetylene compound that plays a significant role in organic synthesis for constructing complex molecular frameworks. The trimethylsilyl groups in its structure provide protection for the ethynyl functional groups, which can be removed under mild conditions to reveal reactive alkyne groups. 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE has been instrumental in the preparation of functional materials and the development of novel drug molecules, as well as in the study of molecular structure and reactivity.

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  • 38170-80-8 Structure
  • Basic information

    1. Product Name: 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE
    2. Synonyms: 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE;TIMTEC-BB SBB008996;1,3-Bis(trimethylsilyl)ethynylübenzene, 96%;1,3-bis(2-(trimethylsilyl)ethynyl)benzene
    3. CAS NO:38170-80-8
    4. Molecular Formula: C16H22Si2
    5. Molecular Weight: 270.52
    6. EINECS: N/A
    7. Product Categories: Acetylenes;Acetylenic Hydrocarbons having Benzene Ring;Ethynylsilanes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds
    8. Mol File: 38170-80-8.mol
  • Chemical Properties

    1. Melting Point: 57 °C
    2. Boiling Point: 304.9 °C at 760 mmHg
    3. Flash Point: 120.9 °C
    4. Appearance: /
    5. Density: 0.92 g/cm3
    6. Vapor Pressure: 0.00154mmHg at 25°C
    7. Refractive Index: 1.505
    8. Storage Temp.: Refrigerator
    9. Solubility: soluble in Toluene
    10. BRN: 2845239
    11. CAS DataBase Reference: 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE(38170-80-8)
    13. EPA Substance Registry System: 1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE(38170-80-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany:
    5. RTECS:
    6. TSCA: No
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 38170-80-8(Hazardous Substances Data)

38170-80-8 Usage

Uses

Used in Organic Synthesis:
1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE is used as a building block for constructing complex molecular frameworks due to its symmetrical diacetylene structure and the protective role of trimethylsilyl groups.
Used in the Preparation of Functional Materials:
1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE is used as a key component in the synthesis of functional materials such as liquid crystals, organic semiconductors, and polymers, owing to its reactive alkyne groups that can be exposed by removing the trimethylsilyl protection.
Used in Pharmaceutical Development:
1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE is used as a starting material in the development of novel drug molecules, leveraging its unique structure and reactivity for designing new therapeutic agents.
Used in Molecular Structure and Reactivity Studies:
1,3-BIS[(TRIMETHYLSILYL)ETHYNYL]BENZENE serves as a model compound in the study of molecular structure and reactivity, providing insights into the behavior of symmetrical diacetylene compounds and their potential applications in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 38170-80-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,1,7 and 0 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 38170-80:
(7*3)+(6*8)+(5*1)+(4*7)+(3*0)+(2*8)+(1*0)=118
118 % 10 = 8
So 38170-80-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H22Si2/c1-17(2,3)12-10-15-8-7-9-16(14-15)11-13-18(4,5)6/h7-9,14H,1-6H3

38170-80-8 Well-known Company Product Price

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  • Alfa Aesar

  • (L10640)  1,3-Bis[(trimethylsilyl)ethynyl]benzene, 96%   

  • 38170-80-8

  • 1g

  • 280.0CNY

  • Detail
  • Alfa Aesar

  • (L10640)  1,3-Bis[(trimethylsilyl)ethynyl]benzene, 96%   

  • 38170-80-8

  • 5g

  • 1045.0CNY

  • Detail

38170-80-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-Bis[(trimethylsilyl)ethynyl]benzene

1.2 Other means of identification

Product number -
Other names 1,3-Bis((trimethylsilyl)ethynyl)benzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:38170-80-8 SDS

38170-80-8Relevant articles and documents

Synthesis of a bifunctional boron-Lewis acid and studies on host-guest chemistry using pyridine and TMPD

Mitzel, Norbert W.,Neumann, Beate,Rudlof, Jens,Stammler, Hans-Georg

, (2021/12/27)

Based on the previously described bifunctional Lewis acid with a functional distance of the boron functions of 4.918(2) ?, the development of a further bifunctional, boron-containing Lewis acid with a wider functional distance is demonstrated. Again, a st

Symmetric molecules with 1,4-triazole moieties as potent inhibitors of tumour-associated lactate dehydrogenase-A

Altamimi, Abdul-Malek S.,Abdel-Gawad, Sherif A.,Alafeefy, Ahmed M.,Balode, Agnese,Vozny, Igor,Pustenko, Aleksandrs,?alubovskis, Raivis,El Shikh, Mohey Eldin,Alasmary, Fatmah A. S.

, p. 147 - 150 (2018/01/02)

A series of symmetric molecules incorporating aryl or pyridyl moieties as central core and 1,4-substituted triazoles as a side bridge was synthesised. The new compounds were investigated as lactate dehydro-genase (LDH, EC 1.1.1.27) inhibitors. The cancer associated LDHA isoform was inhibited with IC50 = 117–174?μM. Seven compounds exhibited better LDHA inhibition (IC50 117–136?μM) compared to known LDH inhibitor–galloflavin (IC50 157?μM).

Control of supramolecular nanoassemblies by tuning the interactions of bent-shaped rod-coil molecules

You, Shengnan,Zhong, Keli,Jin, Long Yi

, p. 3334 - 3340 (2017/07/10)

Rod-coil molecules 1a, 1b and 2a, 2b, consisting of biphenyl and phenyl units connected by an acetylene bond as the rod segment and oligo(ethylene glycol) (OEG) as the coil segment, were synthesized and characterized. Molecules 1a and 1b incorporate a but

Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)

Liu, Xu,Han, Zhaobin,Wang, Zheng,Ding, Kuiling

, p. 1073 - 1078 (2014/08/18)

A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed into the corresponding borane-protected chiral PCP-type pincer ligand 7a with high enantiomeric excess, exemplifying a viable synthetic route to optically active chiral PCP pincer ligands.

Aerobic oxynitration of alkynes with tBuONO and TEMPO

Dutta, Uttam,Maity, Soham,Kancherla, Rajesh,Maiti, Debabrata

supporting information, p. 6302 - 6305 (2015/02/19)

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Expedient synthesis of SMAMPs via click chemistry

Fu, Tsung-Hao,Li, Yan,Thaker, Hitesh D.,Scott, Richard W.,Tew, Gregory N.

supporting information, p. 841 - 845 (2013/10/01)

A novel series of synthetic mimics of antimicrobial peptides (SMAMPs) containing triazole linkers were assembled using click chemistry. While only moderately active in buffer alone, an increase in antimicrobial activity against Staphylococcus aureus and Escherichia coli was observed when these SMAMPs were administered in the presence of mouse serum. One compound had minimum inhibitory concentrations (MICs) of 0.39 μg/mL and 6.25 μg/mL, respectively, and an HC50 of 693 μg/mL. These values compared favorably to peptide-based antimicrobials. A correlation between the net positive charge and SMAMP antimicrobial activity was observed. The triazole linker, an amide surrogate, was found to provide better antimicrobial activity against both S. aureus and E. coli when compared to other analogues.

Synthesis and biological evaluation of new bis-indolone-N-oxides

Najahi, Ennaji,Valentin, Alexis,Tene, Nathan,Treilhou, Michel,Nepveu, Francoise

, p. 16 - 21 (2013/07/27)

A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They did not cause any haemolysis (300 μg mL-1). Of the synthesized bis-indolones, compound 1a had the most potent antiplasmodial activity (IC50 = 0.763 μmol L-1 on the FcB1 strain) with a selectivity index (CC50 MCF7/IC 50 FcB1) of 35.6. No potency against the tested microbial strains was observed.

Ph(O) group for protection of terminal acetylenes

Yang, Xin,Matsuo, Daisuke,Suzuma, Yoshinori,Fang, Jing-Kun,Xu, Feng,Orita, Akihiro,Otera, Junzo,Kajiyama, Shingo,Koumura, Nagatoshi,Hara, Kohjiro

supporting information; experimental part, p. 2402 - 2406 (2011/11/05)

A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coup

Intramolecular hydrogen bonds preorganize an aryl-triazole receptor into a crescent for chloride binding

Lee, Semin,Hua, Yuran,Park, Hyunsoo,Flood, Amar H.

supporting information; experimental part, p. 2100 - 2102 (2010/06/20)

Figure presented Aryl-triazole pentads have been preorganized with intramolecular hydrogen bonds to enhance chloride binding. This outcome highlights the dual hydrogen bond donor and acceptor properties of 1,2,3-triazoles.

Counting the monomers in nanometer-sized oligomers by pulsed electron-electron double resonance

Bode, Bela E.,Margraf, Dominik,Plackmeyer, Joern,Duerner, Gerd,Prisner, Thomas F.,Schiemann, Olav

, p. 6736 - 6745 (2008/02/09)

In a lot of cases active biomolecules are complexes of higher order, thus methods capable of counting the number of building blocks and elucidating their geometric arrangement are needed. Therefore, we experimentally validate here spin-counting via 4-puls

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