| Identification | More | [Name]
Triphenylene | [CAS]
217-59-4 | [Synonyms]
1,2:3,4-DIBENZNAPHTHALENE
9,10-BENZOPHENANTHRENE
BENZO(L)PHENANTHRENE
ISOCHRYSENE
TRIPHENYLENE
9,10-Benzphenanthrene
benzo(1)phenanthrene
Triphenylene (purity)
TRIPHENYLENE, FOR FLUORESCENCE
52687, Triphenylene (purity)
TRIPHENYLENE, 100MG, NEAT
TRIPHENYLENE OEKANAL, 100 MG
benzo(l)phenathrene
benzo[e]phenanthrene | [EINECS(EC#)]
205-922-9 | [Molecular Formula]
C18H12 | [MDL Number]
MFCD00001108 | [Molecular Weight]
228.29 | [MOL File]
217-59-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige crystalline needles | [Melting point ]
195-198 °C(lit.)
| [Boiling point ]
438 °C(lit.)
| [density ]
1.302 | [refractive index ]
1.5500 (estimate) | [Fp ]
438°C | [storage temp. ]
2-8°C | [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) | [IARC]
3 (Vol. Sup 7, 92) 2010 | [NIST Chemistry Reference]
Triphenylene(217-59-4) | [EPA Substance Registry System]
217-59-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H318-H410 | [Precautionary statements ]
P273-P280-P305+P351+P338-P391-P501 | [Hazard Codes ]
Xi,N | [Risk Statements ]
R41:Risk of serious damage to eyes. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S60:This material and/or its container must be disposed of as hazardous waste .
S39:Wear eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3077 9/PG 3 | [WGK Germany ]
3
| [RTECS ]
YK2925000
| [HazardClass ]
9 | [PackingGroup ]
Ⅲ | [HS Code ]
29029090 |
| Hazard Information | Back Directory | [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. | [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. | [Definition]
ChEBI: An ortho-fused polycyclic arene consisting of four fused benzene rings. | [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.
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