ナフタセン

Naphthacene

HCID 7080

基本情報

CAS
92-24-0
標準SMILES
c1ccc2cc3cc4ccccc4cc3cc2c1
InChIKey
IFLREYGFSNHWGE-UHFFFAOYSA-N
分子式
C18H12
平均分子量
228.3 g/mol
単同位体質量
228.09390038

名称と識別子

優先名称
Naphthacene
IUPAC
tetracene
現地名
ナフタセン
英語名
NAPHTHACENE
分子式
C18H12
分子量
228.29

名称と別名

NaphthaceneTETRACENE92-24-02,3-BenzanthraceneBenz[b]anthraceneChrysogenRubeneBenz(b)anthracene2,3-BenzanthreneQYJ5Z6712RDTXSID4059045CHEBI:32600
名称をさらに表示
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ナフタセン (昇華精製品)2,3-ベンゾアントラセン (昇華精製品)テトラセン (昇華精製品)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ベンズ[B]アントラセンテトラセン (ナフタセン)ベンゾ[B]アントラセン2,3-ベンズアントラセン, 50 µg/mL in TolueneTetracenMethaceneNAPHTHYCENETetrabenzeneNaphthacene>
RefChem:164592DTXCID6048751202-138-9MFCD00003702EINECS 202-138-9UNII-QYJ5Z6712RNaphthacene (>80%)NAPHTHACENE [MI]

データベース識別子

CAS
92-24-0
PubChem CID
7080
DTXSID
DTXSID4059045
ChEMBL
CHEMBL1797272
ChEBI
CHEBI:32600
UNII
QYJ5Z6712R
EC Number
202-138-9
Nikkaji
J1.536.811J、J4.651E

物性

構造計算による物性

XLogP
5.9
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

Melting Point357 °C. [ChemIDplus]
Physical Description"Orange leaflets from xylene"; melting point = 341 degrees C; [Merck Index] Has slight green fluorescence in daylight; [Hawley]
Kovats Retention Index · 2 件

2395;2425;2436;2386;405.7;403.9;405;403.9

2426;2425;403.5;403.15;402.86;407.3;401.28;403.52;403.51;403.7;403.89;408.3;408.3

物理化学的性質

融点
300 °C · >300 °C(lit.)
沸点
305.1 °C · 305.1°C (rough estimate)
比重(密度)
1.35 · 1.35
屈折率
1.55 · 1.5500 (estimate)
外見
結晶性粉末
色
オレンジ

化学的性質

化学的特性orange powder

安全と法規制

GHS分類

GHS Classification · 5 件

Warning

H302 (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.

危険有害性情報

Regulatory InformationChemical: Naphthacene
Hazards SummaryAn eye, skin, and respiratory tract irritant; May be harmful if swallowed, inhaled or absorbed through the skin; [MSDSonline] May explode if shocked; [Hawley] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesAcute Tox. 4 (20%);Acute Tox. 4 (20%);Acute Tox. 4 (20%);Aquatic Acute 1 (80%);Aquatic Chronic 1 (80%)

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 ClassificationNot listed by IARC. IARC has evaluated related PAHs (L2154).

法規制情報

Regulatory InformationChemical: Naphthacene

安全データ

wgk
3
tsca
TSCA listed
rtecs
QI7605000
ridadr
UN 3077 9/PG 3
hs_code
29029090
risk_code
40-50/53

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 · 2 件

Present in coal tar and contaminates commercial anthracene; [Merck Index] Used in organic synthesis; [Hawley]

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)

General Manufacturing InformationNaphthacene: ACTIVE
応用分野 · 2 件

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.

調製方法 · 1 件

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.]

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補足説明

定義ChEBI: An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.

関連反応

11 件

化合物ノート

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