Triphenylene 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

InChIKey

SLGBZMMZGDRARJ-UHFFFAOYSA-N

CAS DataBase Reference

217-59-4(CAS DataBase Reference)

NIST Chemistry Reference

Triphenylene(217-59-4)

IARC

3 (Vol. Sup 7, 92) 2010

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

MSDS

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

Triphenylene 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.

Purification Methods

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

Triphenylene(217-59-4)Related Product Information

• 1,12-BENZOPERYLENE
• Benzothiazole
• Benzimidazole
• Benzo[a]pyrene
• 2-Mercaptobenzothiazole
• 1H-Benzotriazole
• Benzofuran
• Hexafluoroacetone trihydrate
• Boron tribromide
• Trimethylolpropane tris(2-methyl-1-aziridinepropionate)
• Tri-tert-butylphosphine
• BENZO[E]PYRENE
• 1.12,2.3,4.5,6.7,8.9,10.11-HEXABENZOCORONENE
• (12aS,13S)-3,7-Dimethoxy-6,13-dihydroxy-9,10,11,12,12a,13-hexahydro-9a-aza-9aH-cyclopenta[b]triphenylene
• triphenylene,1,2,3,4,5,6,7,8,9,10,11,12-dodecahydro
• 2,7-Dihydroxy-3,6,10,11-tetrakis(pentyloxy)triphenylene,3,6,10,11-Tetrakis(pentyloxy)triphenylene-2,7-diol
• Phenanthrene
• BENZO[B]TRIPHENYLENE