ジベンゾ-18-クラウン6-エーテル
ジベンゾ-18-クラウン6-エーテル · 2,2'-[オキシビス(エチレンオキシ)][1,1'-[オキシビス(エチレンオキシ)]ビスベンゼン] · 2,2'-[オキシビス(エチレンオキシ)]-[1,1'-[オキシビス(エチレンオキシ)]ビスベンゼン] · 1,2-[1,2-フェニレンビス(オキシエチレンオキシエチレンオキシ)]ベンゼン · ジベンゾ-18-クラウン-6 · 1,2-[2,1-フェニレンビス(オキシエチレンオキシエチレンオキシ)]ベンゼン · 6,7,9,10,17,18,20,21-オクタヒドロ-5,8,11,16,19,22-ヘキサオキサジベンゾ[a,j]シクロオクタデセン · 3,6,9,12,15,18-ヘキサオキサ-1,2:10,11-ジベンゾ-1,10-シクロオクタデカジエン
識別子と物理属性
| CAS No. | 14187-32-7 |
|---|---|
| 分子式 | C20H24O6 |
| 平均分子量 | 360.4 g/mol |
| 単同位体質量 | 360.15728849 g/mol |
| SMILES | c1ccc2c(c1)OCCOCCOc1ccccc1OCCOCCO2 |
| InChIKey | YSSSPARMOAYJTE-UHFFFAOYSA-N |
| PubChem CID | 26541 |
| ChEMBL | CHEMBL345536 |
| ChEBI | CHEBI:358732 |
| EC No. | 238-041-3 |
| DTXSID | DTXSID6022428 |
| 現地名 | ジベンゾ-18-クラウン6-エーテル |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 極性表面積 | 55.4 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 0 |
| 重原子数 | 26 |
| 形式電荷 | 0 |
| 複雑度 | 300 |
| 物質分類 | Other Classes -> Other Organic Compounds |
| SpringerMaterials Properties | Fusion temperature |
| LogP（分配係数） | 2.2 |
| Physical Description | Light beige fibers or powder[Alfa Aesar MSDS] |
| 融点 | 162-164 °C (lit.) |
| 沸点 | 380-384 °C (679 mmHg) |
| 密度 | 1.1801 (rough estimate) |
| 屈折率 | 1.5200 (estimate) |
| 引火点 | 380-384°C/679mm |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 0.007g/l難溶性 |
| 外観・状態 | ふわふわパウダー |
| 色 | 白～ややベージュ |
| Merck | 14,2602 |
| BRN | 1162153 |
| InChI | 1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2 |
| InChIKey | YSSSPARMOAYJTE-UHFFFAOYSA-N |
| SMILES | C1COc2ccccc2OCCOCCOc3ccccc3OCCO1 |
| CAS データベース | 14187-32-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Dibenzo-18-crown-6(14187-32-7) |
| EPAの化学物質情報 | Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- (14187-32-7) |
化学的特性
white to slightly beige fluffy powder
安全性と法規制
| GHS 分類 | WarningH315 (35.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-Dibenzob,k1,4,7,10,13,16hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A mild skin and moderate eye irritantCauses convulsions, lung changes and other liver changes in oral lethal-dose studies of rats[RTECS] Crown ethers have caused convulsions, liver injury, and dermatitis in experimental animalsA skin and strong eye irritant[Alfa Aesar MSDS] See 18-Crown-6. |
| Hazard Classes and Categories | Skin Irrit. 2 (35.9%) |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | HP5386000 |
| 毒性 | LD50 orally in Rabbit: 2600 mg/kg |
| 税関コード | 29329995 |
| 危険文句（R） | 36-36/37/38-20/21/22 |
| 危険表示 | Xi,Xn |
| hazard_note | Irritant |
| 安全措置（S） | 26-37/39-36 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成、分析用試薬
説明
Dibenzo-18-crown-6 (DB18C6) is the first crown ether synthesized by Pedersen in 1967 and has the strongest binding affinity to a potassium cation (K+) among alkali metal cations. With the similarity of the sizes between K+ and the cavity of crown ether, it had long been believed that the binding selectivity comes from the size relationship between the metal cation and the cavity. However, it was reported that under identical experimental conditions, K+ bound strongly to all crown ethers (12-crown-4 to 24-crown-8) irrespective of the ring size among other cations such as Na+, Ca2+, and NH4+. Moreover, in the gas phase, 18-crown-6 (18C6) and dibenzo18-crown-6 (DB18C6) form preferential complexation in the order Li+ > Na+ > K+ > Rb+ > Cs+, while in the aqueous solution both of them show highest complexion capacity for K+ rather than Li+[1-2].
使用
Dibenzo-18-crown-6, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is an important organic intermediate.
製法・合成法
純化方法
Crystallise it from *benzene, n-heptane or toluene and dry it under vacuum at room temperature for several days. [Szezygiel J Phys Chem 91 1252 1987, V.gtle ed. Top Corr Chem (Host Guest Complex Chemistry) 98 1981.]