ChemicalBook Product Catalog Chemical Reagents Organic reagents Polycyclic compound Triphenylene

Triphenylene

Product NameTriphenylene
CAS217-59-4
MFC18H12
MW228.29
EINECS205-922-9
MOL File217-59-4.mol

Chemical Properties

Melting point	195-198 °C(lit.)
Boiling point	438 °C(lit.)
Density	1.302
refractive index	1.5500 (estimate)
Flash point	438°C
storage temp.	Sealed in dry,Room Temperature
solubility	Soluble in ethanol, benzene, acetic acid, oils and chloroform.
form	Crystalline Needles
color	White to beige
Water Solubility	6.6ug/L(25.00 ºC)
λmax	335nm(Hexane)(lit.)
Merck	14,9740
BRN	1342908
Henry's Law Constant	6.4×10¹ mol/(m³Pa) at 25℃, Duchowicz et al. (2020)
Major Application	environmental
InChI	1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
InChIKey	SLGBZMMZGDRARJ-UHFFFAOYSA-N
SMILES	c1ccc2c(c1)c3ccccc3c4ccccc24
CAS DataBase Reference	217-59-4(CAS DataBase Reference)
IARC	3 (Vol. Sup 7, 92) 2010
NIST Chemistry Reference	Triphenylene(217-59-4)
EPA Substance Registry System	Triphenylene (217-59-4)

Safety Information

Hazard Codes	Xi,N
Risk Statements	41-50/53
Safety Statements	22-24/25-61-60-39-26
RIDADR	UN 3077 9/PG 3
WGK Germany	3
RTECS	YK2925000
HazardClass	9
PackingGroup	Ⅲ
HS Code	29029090
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1

MSDS

Provider	Language
9,10-Benzophenanthrene	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to beige crystalline needles

Uses

Triphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar. Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.

Definition

ChEBI: Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.

Application

Triphenylene is an important basic skeleton monomer of polycyclic aromatic hydrocarbons. It can be used to synthesize macromolecular compounds with multi-conjugated structure, and is widely used in the research of organic supramolecular materials.Triphenylene is used in optics and electronics. It is also used as a discotic mesogen in liquid crystalline materials. Further, it is a compound that fluoresces in the ultraviolet region. In addition to this, it is used in the preparation of triphenylene-2-carbaldehyde.

Preparation

Triphenylene synthesis: 2-Chlorobenzoic acid(78mg, 0.5mmol), iodonium salt (236mg, 0.55mmol), palladium acetate (2.8mg, 0.0125mmol), potassium carbonate (152mg, 1.1mmol) were dissolved in 3mL of NMP solvent was heated to 110 °C and stirred for 17 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to column chromatography to obtain 92 mg of triphenylene as a white solid, The yield was 80%.

Synthesis Reference(s)

Synthesis, p. 756, 1992 DOI: 10.1055/s-1992-26218

General Description

Triphenylene belongs to the class of polycyclic aromatic hydrocarbons, which is commonly employed as a substrate for use as a precursor for the synthesis of graphenes, carbon nanotubes, buckminsterfullerenes as well as polycyclic heteroaromatics.

Synthesis

Triphenylene can be synthesized by a novel ligand-free Pd-catalyzed cascade reaction between o-chlorobenzoic acids and cyclic diaryliodonium salts.^[1]

Purification Methods

Purify triphenylene by zone refining or crystallisation from EtOH or CHCl3 and sublime. [Beilstein 5 IV 2556.]

References

[1] Shuai Yang.“Synthesis of Functionalized Triphenylenes via a Traceless Directing Group Strategy.” Organic Letters 20 6 (2018): 1491–1495.