1-アダマンタノール
1-アダマンタノール · 1-ヒドロキシアダマンタン · トリシクロ[3.3.1.13,7]デカン-1-オール · アダマンタン-3-オール · ヒドロキシアダマンタン · 1-アダマンチルアルコール · アダマンタン-1-オール · (1-アダマンチル)アルコール
識別子と物理属性
| CAS No. | 768-95-6 |
|---|---|
| 分子式 | C10H16O |
| 平均分子量 | 152.23 g/mol |
| 単同位体質量 | 152.12011513 g/mol |
| SMILES | OC12CC3CC(CC(C3)C1)C2 |
| InChIKey | VLLNJDMHDJRNFK-UHFFFAOYSA-N |
| PubChem CID | 64152 |
| ChEMBL | CHEMBL2041310 |
| EC No. | 212-202-8 |
| DTXSID | DTXSID10227620 |
| 現地名 | 1-アダマンタノール |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 20.2 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 144 |
| SpringerMaterials Properties | Coriolis coupling |
| 融点 | 247 °C (subl.) (lit.) |
| 沸点 | 214.73°C (rough estimate) |
| 密度 | 0.8544 (rough estimate) |
| 屈折率 | 1.4880 (estimate) |
| 引火点 | 240°C |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | クロロホルム（少量）、メタノール（少量）エタノール、メタノール、ジエチルエーテルに可溶。水に部分的に混和する。 |
| 外観・状態 | 結晶性粉末または針 |
| pKa（酸解離定数） | 15.38±0.20(Predicted) |
| 色 | ホワイトからオフホワイト |
| BRN | 1903952 |
| ヘンリー定数 | 6.0×100 mol/(m3Pa) at 25℃, Roon et al. (2005) |
| InChI | 1S/C10H16O/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2/t7-,8+,9-,10- |
| InChIKey | VLLNJDMHDJRNFK-UHFFFAOYSA-N |
| SMILES | OC12C[C@H]3C[C@H](C[C@H](C3)C1)C2 |
| CAS データベース | 768-95-6(CAS DataBase Reference) |
| NISTの化学物質情報 | 1-Adamantanol(768-95-6) |
化学的特性
white to off-white crystalline powder or needles
安全性と法規制
| GHS 分類 | DangerH228 (33.3%): Flammable solid [Danger Flammable solids]P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Flam. Sol. 2 (33.3%) |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | AU4980000 |
| 税関コード | 29061900 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (4)-1945 |
| 危険表示 | Xi |
| hazard_note | Irritant |
| 安全措置（S） | 22-24/25-36-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
1-Adamantanol is a cyclic molecule with a hydroxyl group. It is produced by the oxidation of 2-methyl-2-adamantanol. 1-Adamantanol has been shown to be an effective substrate for bioremediation in wastewater treatment plants and can be used as a precursor to produce trifluoroacetic acid.
使用
1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.
製法・合成法
純化方法
If 2-adamantanol is a suspected impurity, then dissolve the substance (10g) in acetone (100mL) and add Jones's reagent [CrO3 (10.3g) in H2O (30mL)], then conc H2SO4 (8.7mL) is added dropwise (turns green in colour) until excess reagent is present (slight red colour). Stir overnight, decant the acetone solution from the Cr salts and adamantan-2-one, dry (Na2SO4) and evaporate to dryness. The residue (ca 7g) is chromatographed through Al2O3 (250g) and washed with 50% *benzene/pet ether (b 40-60o), then 100% Et2O (to remove any adamantan-2-one present) and the 1-adamantanol is then eluted with 5% MeOH in Et2O. The eluate is evaporated, and the residue is recrystallised from pet ether (b 30-60o) at -70o, m 287.2-288.5o. It also crystallises from MeOH and can be sublimed in vacuo. It has characteristic IR, max 3640, 1114, 1086, 982 and 930cm-1. [Schleyer & Nicholas J Am Chem Soc 83 182 1961.] [Beilstein 6 IV 391.] Alternatively, if free from the 2-isomer, dissolve it in tetrahydrofuran, dilute with H2O to precipitate the alcohol. Collect, dry and sublime it in a vacuum at 130o. [Stetter et al. Chem Ber 92 1629 1959.]