Triphenylen

Triphenylene

HCID 9170CAS 217-59-4

Grundinformationen

Standard-SMILES
c1ccc2c(c1)c1ccccc1c1ccccc21
InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N
Summenformel
C18H12
Durchschnittliche Molmasse
228,3 g/mol
Monoisotopische Masse
228,09390038

Überblick

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

Namen und Bezeichner

Bevorzugter Name
Triphenylene
IUPAC
triphenylene
Lokaler Name
Triphenylen
Englischer Name
Triphenylene
Summenformel
C18H12
Molmasse
228.29

Namen und Synonyme

TRIPHENYLENE217-59-49,10-BenzophenanthreneIsochrysene9,10-BenzphenanthreneBenzo(l)phenanthreneBenzo[l]phenanthrene1,2,3,4-DibenznaphthaleneDTXSID9059757NSC-5745518WX3373I0CHEBI:33080
Weitere Namen anzeigen
Triphenylene,98%benzo(1)phenanthreneriphenyleneTriphenylene 98%Triphenylene >benzo(l)phenathrene
RefChem:191904DTXCID7036537205-922-9MFCD00001108triphenylene (purity)1,2:3,4-Dibenznaphthalene53814-75-8triphenylen

Datenbank-Bezeichner

CAS
217-59-4
PubChem CID
9170
DTXSID
DTXSID9059757
ChEMBL
CHEMBL1797416
ChEBI
CHEBI:33080
UNII
18WX3373I0
EC Number
205-922-9
Nikkaji
J6.134D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,9
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
18

Experimentelle und physikochemische Eigenschaften

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.84
Physical DescriptionLight yellow powder, insoluble in water; [MSDSonline]
Collision Cross Section143.6 Ų [M*]+

Physikochemische Eigenschaften

Schmelzpunkt
195 · 195-198 °C(lit.)
Siedepunkt
438 °C · 438 °C(lit.)
Dichte
1.302 · 1.302
Brechungsindex
1.55 · 1.5500 (estimate)
Flammpunkt
438 °C · 438°C
storage temp.
Sealed in dry,Room Temperature

Sicherheit und Regulatorisches

Gefahrenhinweise

Hazards SummaryAn irritant; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

Toxikologische Informationen

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1 Eintrag

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen Classification · 6 Einträge

Triphenylene

Group 3: Not classifiable as to its carcinogenicity to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2010

2005

3, not classifiable as to its carcinogenicity to humans. (L135)

Sicherheitsdaten

wgk
3
ridadr
UN 3077 9/PG 3
hs_code
29029090
RTECS-Nr.
YK2925000
risk_code
41-50/53
hazard_code
Xi,N

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

Verwendung und Herstellung

Uses · 1 Eintrag

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

Anwendungen

VerwendenTriphenylene 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.

Darstellung · 1 Eintrag

synthetischeTriphenylene 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%.

Ergänzende Hinweise

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

Zugehörige Reaktionen

10

Verknüpfte Notizen

Wird geladen…