2,3,6,7,10,11-Hexabromotriphenylene

• CAS: 82632-80-2
• Catalog Number: ACM82632802-2
• Category: Main Products
• Molecular Weight: 701.66
• Molecular Formula: C18H6Br6
• Synonyms: Triphenylene, 2,3,6,7,10,11-hexabromo-
• IUPAC Name: 2,3,6,7,10,11-hexabromotriphenylene
• SMILES: C1=C2C3=CC(=C(C=C3C4=CC(=C(C=C4C2=CC(=C1Br)Br)Br)Br)Br)Br
• InChI: InChI=1S/C18H6Br6/c19-13-1-7-8(2-14(13)20)10-4-17(23)18(24)6-12(10)11-5-16(22)15(21)3-9(7)11/h1-6H
• InChI Key: GLHQUXLCQLQNPZ-UHFFFAOYSA-N
• Boiling Point: 689.8 ± 50.0 °C(predicted)
• Density: 2.428 ± 0.06 g/mL (predicted)
• Appearance: Grey solid powder
• Complexity: 364
• Covalently-Bonded Unit Count: 1
• Exact Mass: 701.55083g/mol
• Formal Charge: 0
• Hazard Statements: H315 : Causes skin irritation.H319 : Causes serious eye irritation.
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Heavy Atom Count: 24
• Monoisotopic Mass: 695.55698g/mol
• Precautionary Statements: P264 : Wash skin thoroughly after handling.P280 : Wear protective gloves/ eye protection/ face protection.P337 + P313 : If eye irritation persists: Get medical advice/ attention.P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.P332 + P313 : If skin irritation occurs: Get medical advice/ attention.P362 : Take off contaminated clothing and wash before reuse.
• Rotatable Bond Count: 0
• Signal Word: Warning
• Solubility In Water: Insoluble
• XLogP3: 9

Case Study

2,3,6,7,10,11-Hexabromotriphenylene as a Key Intermediate for Advanced Discotic Liquid Crystal Semiconductors

Hoang, Mai Ha, et al. Chemistry letters 39.4 (2010): 396-397.

Discotic liquid crystalline materials, particularly those based on a triphenylene core, show great promise for optoelectronic applications. 2,3,6,7,10,11-hexabromotriphenylene (hexabromo-TP) was employed as the reactive core in a modular Sonogashira coupling sequence to attach six ethynyl-linked, π-extended side groups (4-(5-dodecylthiophen-2-yl)phenyl acetylene units), producing a hexakis-substituted triphenylene discotic semiconductor. As a multifunctional electrophile, the hexabrominated core enabled high substitution density and rapid access to a fully conjugated, planar disc.
Synthesis Strategy: Sequential cross-couplings were used to prepare the sidearm (via Suzuki and Sonogashira steps) and to convert it into the terminal alkyne partner. The terminal alkyne sidearm was then coupled to 2,3,6,7,10,11-hexabromotriphenylene by Sonogashira chemistry to give the target hexakis-ethynylated triphenylene derivative (HDTPT, compound 6). The reported isolated yield for this final coupling was ≈60%.
Material Properties: The synthesized LC material demonstrated good solubility and self-organized into long fiber structures with supramolecular columnar stacks. It also showed a relatively low band gap energy of 2.53 eV, making it more suitable for electronic and optoelectronic applications compared to many previously reported triphenylene derivatives.

2,3,6,7,10,11-Hexabromotriphenylene as a Critical Building Block for Advanced Covalent Organic Frameworks

Du, Changsheng, et al. Chemistry of Materials 35.3 (2023): 1395-1403.

Two-dimensional covalent organic frameworks (2D-COFs) combine crystallinity and permanent porosity, making them attractive as nanocarriers. Here, 2,3,6,7,10,11-hexabromotriphenylene (hexabromo-TP) served as the reactive triphenylene core used to install six peripheral aryl substituents by cross-coupling, enabling synthesis of the hexafunctional monomer 2,3,6,7,10,11-hexakis(4-aminophenyl)triphenylene (HAPTP). The dense, symmetric bromination on the triphenylene scaffold makes it an effective platform for convergent assembly of multifunctional monomers that polymerize into ordered 2D COF sheets.
Synthetic Route: The hexabromo core was coupled with a boronic ester under Suzuki conditions (PdCl2(PPh3)2 catalyst, aqueous K2CO3, 1,4-dioxane) under inert atmosphere and reflux (90 °C, overnight). After aqueous workup and chromatographic purification (ethyl acetate:methanol, 95:5), the hexaaniline triphenylene monomer (HAPTP) was obtained in a yield of ~35%. HAPTP was then polymerized into 2D COFs that self-templated hollow spherical particles via an Ostwald-ripening transformation from solid spheres to hollow shells.
Key Results
The COFs assembled from the hexabromo-derived monomer formed uniform hollow spheres composed of highly crystalline nanosheets and even hexagonal single crystals (TEM evidence). The self-templated pathway eliminated the need for sacrificial templates while delivering uniform particle populations.
The controlled morphology and crystallinity produced COF particles with very high pore volume (up to 1.947 cm3/g), enhancing their capacity as nanocarriers for controlled drug delivery.

Custom Q&A

What is the molecular formula of 2,3,6,7,10,11-Hexabromotriphenylene?

The molecular formula of 2,3,6,7,10,11-Hexabromotriphenylene is C18H6Br6.

When was the structure of 2,3,6,7,10,11-Hexabromotriphenylene created and last modified?

The structure was created on October 26, 2006, and last modified on December 30, 2023.

What is the IUPAC Name of 2,3,6,7,10,11-Hexabromotriphenylene?

The IUPAC Name of 2,3,6,7,10,11-Hexabromotriphenylene is 2,3,6,7,10,11-hexabromotriphenylene.

What is the InChIKey of 2,3,6,7,10,11-Hexabromotriphenylene?

The InChIKey of 2,3,6,7,10,11-Hexabromotriphenylene is GLHQUXLCQLQNPZ-UHFFFAOYSA-N.

How many hydrogen bond donor counts are there in 2,3,6,7,10,11-Hexabromotriphenylene?

There are 0 hydrogen bond donor counts in 2,3,6,7,10,11-Hexabromotriphenylene.

What is the topological polar surface area of 2,3,6,7,10,11-Hexabromotriphenylene?

The topological polar surface area of 2,3,6,7,10,11-Hexabromotriphenylene is 0.2.

How many heavy atoms are present in 2,3,6,7,10,11-Hexabromotriphenylene?

There are 24 heavy atoms present in 2,3,6,7,10,11-Hexabromotriphenylene.

Is 2,3,6,7,10,11-Hexabromotriphenylene a canonicalized compound?

Yes, 2,3,6,7,10,11-Hexabromotriphenylene is a canonicalized compound.

What is the molecular weight of 2,3,6,7,10,11-Hexabromotriphenylene?

The molecular weight of 2,3,6,7,10,11-Hexabromotriphenylene is 701.7 g/mol.

What is the CAS number of 2,3,6,7,10,11-Hexabromotriphenylene?

The CAS number of 2,3,6,7,10,11-Hexabromotriphenylene is 82632-80-2.