トリフェニレン

Triphenylene

HCID 9170CAS 217-59-4

基本情報

標準SMILES
c1ccc2c(c1)c1ccccc1c1ccccc21
InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N
分子式
C18H12
平均分子量
228.3 g/mol
単同位体質量
228.09390038

概要

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

名称と識別子

優先名称
Triphenylene
IUPAC
triphenylene
現地名
トリフェニレン
英語名
Triphenylene
分子式
C18H12
分子量
228.29

名称と別名

TRIPHENYLENE217-59-49,10-BenzophenanthreneIsochrysene9,10-BenzphenanthreneBenzo(l)phenanthreneBenzo[l]phenanthrene1,2,3,4-DibenznaphthaleneDTXSID9059757NSC-5745518WX3373I0CHEBI:33080
名称をさらに表示
トリフェニレンイソクリセン1,2:3,4-ジベンゾナフタレン9,10-ベンゾフェナントレントリフェニレン (昇華精製品)1,2:3,4-ジベンゾナフタレン (昇華精製品)9,10-ベンゾフェナントレン (昇華精製品)イソクリセン (昇華精製品)トリフェニレン標準品トリフェニレン, IN TOLUENE (200ΜG/ML)トリフェニレン, 50 µg/mL in Tolueneトリフェニレン, 98%ベンゾ[l]フェナントレンTriphenylene,98%benzo(1)phenanthreneriphenyleneTriphenylene 98%Triphenylene >benzo(l)phenathrene
RefChem:191904DTXCID7036537205-922-9MFCD00001108triphenylene (purity)1,2:3,4-Dibenznaphthalene53814-75-8triphenylen

データベース識別子

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

物性

構造計算による物性

XLogP
4.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
18

実験および物理化学的性質

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*]+

物理化学的性質

融点
195 · 195-198 °C(lit.)
沸点
438 °C · 438 °C(lit.)
比重(密度)
1.302 · 1.302
屈折率
1.55 · 1.5500 (estimate)
闪点
438 °C · 438°C
貯蔵温度
Sealed in dry,Room Temperature

化学的性質

化学的特性white to beige crystalline needles

安全と法規制

危険有害性情報

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

毒性情報

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 件

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 件

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)

安全データ

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

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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)

用途と製造

Uses · 1 件

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)

応用分野 · 4 件

解説9,10-benzophenanthrene.C18H12(228.29).トリフェニレンは,石炭タール中に少量存在する炭化水素.o-ブロモヨードベンゼンと金リチウムから合成する.針状結晶.融点198 ℃,沸点425 ℃(昇華).密度1.302 g cm-3.λmax 230,272,281,303,325,353,372 nm(log ε 4.36,4.76,4.30,4.07,3.65,2.64,2.38).エタノール,酢酸,ベンゼンなどに可溶.昇華性があり,ベンゼン溶液は青い蛍光を発する.酸化すればメリト酸を生じる.森北出版「化学辞典(第2版)

用途無色の針状結晶で、紫外線を照射すると青紫色の蛍光を放つ。この性質を利用し、光学、電子デバイスの材料として使われる。

使用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.

一般的な説明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.

調製方法 · 2 件

製造方法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%.

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

補足説明

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

関連反応

10 件

関連ノート

読み込み中…