ナフタセン
ナフタセン · 2,3-ベンゾアントラセン · クリソゲン · テトラセン【炭化水素】 · ルベン · テトラセン · 2,3-ベンズアントラセン · 2,3-ベンズアントラセン標準品
識別子と物理属性
| CAS No. | 92-24-0 |
|---|---|
| 分子式 | C18H12 |
| 平均分子量 | 228.3 g/mol |
| 単同位体質量 | 228.09390038 g/mol |
| SMILES | c1ccc2cc3cc4ccccc4cc3cc2c1 |
| InChIKey | IFLREYGFSNHWGE-UHFFFAOYSA-N |
| PubChem CID | 7080 |
| ChEMBL | CHEMBL1797272 |
| ChEBI | CHEBI:32600 |
| EC No. | 202-138-9 |
| DTXSID | DTXSID4059045 |
| 現地名 | ナフタセン |
化学・物理的性質
| XLogP | 5.9 |
|---|---|
| 極性表面積 | 0 |
| 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 | 236 |
| 融点 | 357 °C. [ChemIDplus]>300 °C(lit.) |
| Physical Description | "Orange leaflets from xylene"melting point = 341 degrees C[Merck Index] Has slight green fluorescence in daylight[Hawley] |
| Kovats Retention Index | 2395242524362386405.7403.92426403.5403.15402.86407.3401.28403.52403.51403.7403.89408.3 |
| 沸点 | 305.1°C (rough estimate) |
| 密度 | 1.35 |
| 屈折率 | 1.5500 (estimate) |
| 外観・状態 | 結晶性粉末 |
| 色 | オレンジ |
| 溶解度 | 1.507ug/L(25℃) |
| Merck | 14,6369 |
| BRN | 1909299 |
| ヘンリー定数 | 2.0×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | InChI=1S/C18H12/c1-2-6-14-10-18-12-16-8-4-3-7-15(16)11-17(18)9-13(14)5-1/h1-12H |
| InChIKey | IFLREYGFSNHWGE-UHFFFAOYSA-N |
| SMILES | C1=C2C(C=C3C(=C2)C=C2C(C=CC=C2)=C3)=CC=C1 |
| CAS データベース | 92-24-0(CAS DataBase Reference) |
| EPAの化学物質情報 | Naphthacene (92-24-0) |
化学的特性
orange powder
安全性と法規制
| GHS 分類 | WarningH302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]H400 (80%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (80%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: Naphthacene |
| 有害性の概要 | An eye, skin, and respiratory tract irritantMay be harmful if swallowed, inhaled or absorbed through the skin[MSDSonline] May explode if shocked[Hawley] See POLYCYCLIC AROMATIC HYDROCARBONS. |
| Hazard Classes and Categories | Acute Tox. 4 (20%)Aquatic Acute 1 (80%)Aquatic Chronic 1 (80%) |
| Treatment | There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10) |
| 健康影響 | PAHs 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) |
| 暴露経路 | Oral (L10)inhalation (L10) |
| 毒性の概要 | 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) |
用途
解説
benzo[b]anthracene．C18H12(228.29)．ナフタセンは，テトラセンともいう．コールタールのアントラセン留分中に少量含まれる．ナフタレンに無水フタル酸をフリーデル-クラフツ反応させて2-(2-アントリルカルボニル)安息香酸にし，ついで閉環，さらに水素化脱水すると得られる．橙黄色の結晶．融点357 ℃．濃硫酸に溶けて緑色を呈する．UV(エタノール)λmax 280，420，450，475 nm(log ε 5.4，3.7，4.0，4.1)．アントラセンよりも反応性に富み，光伝導性や常磁性を示す．森北出版「化学辞典（第2版）
一般的な説明
Benz[b]anthracene is an ethylnylated acene that is a conducting polymer, which can be used as a donor material. It has a high photoluminescence and quantum yield that makes it a promising candidate in the development of single crystal electronic material.
製法・合成法
純化方法
Naphthacene crystallises in orange needles from EtOH, *C6H6 or toluene. Dissolve it in sodium-dried *benzene and pass it through a column of alumina. The eluent is evaporated under vacuum, and the chromatography is repeated using fresh *benzene. Finally, the naphthacene is sublimed in vacuo at 186o. [Martin & Ubblehode J Chem Soc 4948 1961, UV: Clar Chem Ber 65 517 1932, Clar Chem Ber 69 607 1936, IR: Cannon & Sutherland Spectrochim Acta 4 373 1951, Beilstein 5 H 718, 5 IV 2545.]