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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 217
実験および物理化学的性質
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
- 溶解性
- エタノール、ベンゼン、酢酸、油、クロロホルムに可溶。
- 外見
- 結晶針
- 色
- 白からベージュ
- 水溶解度
- 6.6 ug/L · 6.6ug/L(25.00℃)
- Merck
- 14 · 14,9740
- BRN
- 1342908 · 1342908
- Henry's Law Constant
- 6.4 · 6.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 主な用途
- 環境
- 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 データベース
- 217 · 217-59-4(CAS DataBase Reference)
- NISTの化学物質情報
- Triphenylene(217-59-4)
- EPAの化学物質情報
- Triphenylene (217-59-4)
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
毒性情報
Toxicity Summary
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)
Carcinogen Classification
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
- safety_code
- 22-24/25-61-60-39-26
- hazard_class
- 9
- packing_group
- Ⅲ
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
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
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
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
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.]
上流・下流製品情報
上流原料
補足説明
定義ChEBI: Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.
関連反応
関連ノート
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