477-75-8

Basic information

• Product Name: TRIPTYCENE
• Synonyms: RARECHEM AQ BC 8A30;TRIPTYCENE;9,10-O-BENZENO-9,10-DIHYDROANTHRACENE;9,10-o-Benzenoanthracene, 9,10-dihydro-;Anthracene, 9,10-dihydro-9,10-O-benzeno-;Tribenzobicyclo[2.2.2]octatriene;Tryptycene;TRIPTYCENE 99%
• CAS NO: 477-75-8
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.33
• EINECS: 207-519-3
• Product Categories: Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 477-75-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 252-254 °C(lit.)
• Boiling Point: 332.54°C (rough estimate)
• Flash Point: 171.7°C
• Appearance: /
• Density: 1.1180 (estimate)
• Vapor Pressure: 2.15E-05mmHg at 25°C
• Refractive Index: 1.7040 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• Merck: 14,9749
• CAS DataBase Reference: TRIPTYCENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPTYCENE(477-75-8)
• EPA Substance Registry System: TRIPTYCENE(477-75-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 477-75-8(Hazardous Substances Data)

Usage

Description

TRIPTYCENE is a rigid, fused-ring skeleton with three-fold symmetry, serving as a structural building block for triptycene-based polymers of intrinsic microporosity. It is characterized by its yellowish-beige to greyish needle-like crystals and has been utilized in various applications due to its unique chemical properties.

Uses

Used in Chemical Analysis:
TRIPTYCENE is used as a reference compound for determining the diffusion coefficients of radical ions, such as those of hexafluorobenzene, diphenylacetylene, triptycene, and tetraphenylnapthalene, in liquid n-hexane and n-hexadecane. This application is crucial for understanding the behavior of these ions in different solvent environments.
Used in Polymer Synthesis:
In the field of polymer chemistry, TRIPTYCENE is used as a structural building block for the synthesis of triptycene-based polymers of intrinsic microporosity (PIMs). These polymers have potential applications in gas separation, storage, and catalysis due to their unique porous structure and high surface area.
Used in Host-Guest Chemistry:
TRIPTYCENE is used as a key component in the synthesis of cylindrical macrotricyclic polyethers containing dibenzo[24]crown-8 cavities. These structures have been proven to be highly efficient hosts for the complexation with paraquat derivatives, which can be useful in various chemical and biological applications, such as sensing and drug delivery.

InChI:InChI=1/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H

Upstream product

• 120-12-7 anthracene 
• 164594-13-2 Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate 
• 1026360-69-9 (Phenyl) iodonium triflate 
• 50-00-0 formaldehyd 
• 59239-90-6 9-triptycyl lithium 
• 229-87-8 phenanthridine 
• 4423-49-8 9,10-[1,2]benzenoanthracen-9(10H)-ylmethanol 
• 33188-82-8 1-chlorotriptycene 
• 462-06-6 fluorobenzene 
• 1072-85-1 o-fluorobromobenzene 
• 109-99-9 tetrahydrofuran 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 1608-42-0 benzenedizolium-2-carboxylate 

Downstream Products

• 20712-00-9 (9r,10r)-2-bromo-9,10-dihydro-9,10-[1,2]benzenoanthracene 

Relevant articles and documents

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Facile Net Loss of a Carbon Atom from a Constrained Intermediate

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Synthesis, Structure, and Complexation Properties of a C3-Symmetrical Triptycene-Based Anion Receptor: Selectivity for Dihydrogen Phosphate

A new anion binding motif based on triptycene core has been synthesized from 2,7,14-trinitrotriptycene. Its well-defined binding pocket allowed for the selective recognition and sensing of dihydrogen phosphate in DMSO-d6 + 0.5% H2O.

Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions

A non-conventional modification of exfoliated few-layer graphene (FLG) with different arynes under microwave (MW) irradiation and solvent-free conditions is reported. The described approach allows reaching fast, efficient and mild covalent functionalization of FLG.

Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature

New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 ? between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields.