1,3,5-TRIETHYNYLBENZENE

Base Information

• Chemical Name: 1,3,5-TRIETHYNYLBENZENE
• CAS No.: 7567-63-7
• Molecular Formula: C12H6
• Molecular Weight: 150.18
• Hs Code.: 29029090
• Mol file: 7567-63-7.mol

Synonyms:1,3,5-Triethynylbenzene;benzene, 1,3,5-triethynyl-;

Chemical Property of 1,3,5-TRIETHYNYLBENZENE

Chemical Property:

• Vapor Pressure: 0.0102mmHg at 25°C
• Melting Point: 105-107°C
• Refractive Index: 1.587
• Boiling Point: 272.258 °C at 760 mmHg
• Flash Point: 107.62 °C
• PSA: 0.00000
• Density: 1.054 g/cm³
• LogP: 1.63050
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Soluble in methanol. Insoluble in water.

Purity/Quality:

97% ^*data from raw suppliers

1,3,5-Triethynylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-20/21-36/37/38-65-36
• Safety Statements: 16-26-36/37/39-60-43-37-33-7

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1,3,5-Triethynylbenzene is a benzene derivative with three ethynyl groups attached at the 1, 3, and 5 positions, serving as a versatile core unit in the synthesis of dendrimers and discotic liquid crystals. Its rigid, star-shaped structure facilitates the construction of shape-persistent polyyne dendrimers through Sonogashira coupling, as well as the formation of discotic nematic phases when combined with oxadiazole-based arms, demonstrating its utility in materials science for applications in electronics, photonics, and advanced liquid crystal systems.

Technology Process of 1,3,5-TRIETHYNYLBENZENE

There total 15 articles about 1,3,5-TRIETHYNYLBENZENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

1,3,5-tris-(1-trimethylsilylethynyl)benzene (18772-58-2) → 1,3,5-Triethynylbenzene (7567-63-7)

Guidance literature:

With water; potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1039/b715550f

Reference yield: 92.0%

2,2',2-(benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(propan-2-ol) (105405-52-5) → 1,3,5-Triethynylbenzene (7567-63-7)

Guidance literature:

With potassium hydroxide; In toluene; at 110 ℃; for 8h;

DOI:10.1016/j.saa.2013.01.047

Reference yield: 91.0%

3,5-[bis(3-hydroxy-3-methyl-1-butynyl)]-1-ethynylbenzene → 1,3,5-Triethynylbenzene (7567-63-7)

Guidance literature:

With methanol; tetra(n-butyl)ammonium hydroxide; In toluene; at 75 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.3762/bjoc.7.55

upstream raw materials:

1,3,5-Tris(1,2-dibromaethyl)benzol

1,3,5-Tris-(1-chlor-vinyl)-benzol

1,3,5-tris((trimethylsilyl)ethynyl)-2,4,6-tris(trimethylsilyl)benzene

1,3,5-tris-(1-trimethylsilylethynyl)benzene

Downstream raw materials:

1,3,5-Tris-(4-nitro-phenylethynyl)-benzene

1,3,5-Tris-(2-methoxy-phenylethynyl)-benzene

1,3,5-tris(4-methoxyphenylethynyl)-benzene

1,3,5-tris([1,1'-biphenyl]-4-ylethynyl)benzene

Refernces

Synthesis of shape-persistent polyal dendrimers - Facile entry to polyene and polyyne dendrimers

10.1002/ejoc.200500055

The research focuses on the synthesis of shape-persistent polyaldehyde (polyal) dendrimers, which are further transformed into polyene and polyyne dendrimers. These dendrimers are constructed using a divergent iterative method, with 1,3,5-triethynylbenzene as the core unit and 2-bromo-5-tert-butyl-1,3-benzenedicarbaldehyde as the building block. The study involves the use of Sonogashira coupling and Corey-Fuchs reaction as key synthetic strategies. Various reactants, including 1,3,5-triethynylbenzene, 2-bromo-5-tert-butyl-1,3-benzenedicarbaldehyde, iodobenzene, and phosphorus-based reagents, are utilized in the synthesis process. The synthesized dendrimers are analyzed using techniques such as NMR spectroscopy, mass spectrometry, and UV/Vis spectroscopy to confirm their structures and properties. The research also explores the thermal stability and fluorescence emission of the synthesized dendrimers, providing insights into their potential applications in electronics, photonics, and materials science.

Star-shaped discotic nematic liquid crystal containing 1,3,5-triethynylbenzene and oxadiazole-based rigid arms

10.1016/S0040-4039(01)00245-3

The research focuses on the synthesis and characterization of a novel three-armed discotic liquid crystal (LC), which is the first star-shaped molecule to exhibit a discotic nematic phase. The purpose of the study was to create a molecule with reduced inter-core interaction, which is necessary for the formation of a nematic phase rather than the more common columnar phase in discotic LCs. The researchers synthesized a molecule based on 1,3,5-triethynylbenzene as the core and 2,5-diphenyloxadiazole as rigid arms. The conclusions drawn from the research were that the unique molecular shape of compound 5, with its long rigid arms and small nonpolar core, contributed to the formation of a discotic nematic assembly rather than a columnar stacking, marking a significant advancement in the field of discotic liquid crystals.