1,3-アダマンタンジカルボン酸
1,3-アダマンタンジカルボン酸 · アダマンタン-1,3-ジカルボン酸 · トリシクロ[3.3.1.13,7]デカン-1,3-ジカルボン酸 · 1,3-ジカルボキシアダマンタン · 1,3‐アダマンタンジカルボン酸 · アダマンタン-1,3-ジカルボン酸, 98% · アダマンタン-3,5-ジカルボン酸 · アダマンタン-1,5-ジカルボン酸
識別子と物理属性
| CAS No. | 39269-10-8 |
|---|---|
| 分子式 | C12H16O4 |
| 平均分子量 | 224.25 g/mol |
| 単同位体質量 | 224.10485899 g/mol |
| SMILES | O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 |
| InChIKey | PAVQGHWQOQZQEH-UHFFFAOYSA-N |
| PubChem CID | 64339 |
| EC No. | 254-395-1 |
| DTXSID | DTXSID40192519 |
| 現地名 | 1,3-アダマンタンジカルボン酸 |
化学・物理的性質
| XLogP | 1.1 |
|---|---|
| 極性表面積 | 74.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 2 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 327 |
| 融点 | 276-278 °C (lit.) |
| 沸点 | 380.6±15.0 °C(Predicted) |
| 密度 | 1.461±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | DMSO（少量）、メタノール（微量、加温） |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 4.24±0.40(Predicted) |
| 色 | ホワイトからオフホワイト |
| InChI | InChI=1S/C12H16O4/c13-9(14)11-2-7-1-8(4-11)5-12(3-7,6-11)10(15)16/h7-8H,1-6H2,(H,13,14)(H,15,16) |
| InChIKey | PAVQGHWQOQZQEH-UHFFFAOYSA-N |
| SMILES | C12(C(O)=O)CC3CC(CC(C(O)=O)(C3)C1)C2 |
| CAS データベース | 39269-10-8(CAS DataBase Reference) |
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract 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 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).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. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (66.7%)Eye Irrit. 2A (66.7%)STOT SE 3 (33.3%) |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | YD1994000 |
| 税関コード | 29172090 |
| 危険文句（R） | 36/37/38 |
| 安全措置（S） | 26-36/37/39 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
使用
1,3-Adamantanedicarboxylic acid is a carboxylic acid derivative of adamantane. It is widely used in drug industry, polymer synthesis and fine chemicals as key intermediates. It is also used as antidepressants or antiparkinsonic drugs in clinical practice.
製法・合成法
製造方法
1,3-Adamantanedicarboxylic acid was synthesized from 1-adamantane carboxylic acid by one-pot method. In this process, the ratio of mixed acid (nitric acid and sulfuric acid) have important effect on the yield, the role of sulfuric acid not only is solvent, but also can improve the oxidate ability of nitric acid.Efficient Synthesis of 1,3-Adamantanedicarboxylic Acid and 1,3-DiaminoadamantaneReaction: 1-Adamantane carboxylic acid (20 g), nitric acid (65 %, 20 mL) and sulfuric acid (98 %, 160 mL) were placed in a three-necked roundbottom flask fitted with an efficient magnetic stirrer and a thermometer. Cooled to 0 oC and held at 0 oC, anhydrous formic acid (80 %, 70 mL) was added dropwise in 5 h and reacted for 1 h. poured to crushed ice, filtered and then washed the precipitate several times with water to give a white solid. Then the white solid was dissolved in aqueous NaOH solution and the upper clear solution was separated and acidified by HCl to pH = 3. Filtered, washed with water, dried in vacuum, recrystallized from ethanol. White solid, yield 22.9 g (92 %). m.p.: 275- 276 oC1H NMR (DMSO-d6, 400 MHz) δ: 1.616 (m, 2H), 1.691-1.727 (m, 4H), 1.759-1.791 (m, 4H), 1.850-1.882 (m, 2H), 2.059 (m, 1H), 12.062 (br, s, 2H, COOH); 13C NMR (100 MHz, DMSO-d6) δ 27.37 (C-5, C-7), 34.98 (C-6), 37.66 (C-4, C-8, C-9, C-10), 39.78 (C-2), 39.89 (C-2, C-3), 177.76 (COOH). IR (KBr, νmax, cm-1) : 2913, 2851, 2636, 1691, 1451, 1410, 1344, 1249, 1103, 1084, 952, 743, 670, 528; Anal. calcd for C12H16O4: C 64.29, H 7.14; found C 64.55, H 7.22.
純化方法
Dissolve the acid in aqueous NaOH, treat with charcoal, filter and acidify with dilute HCl. It crystallises from MeOH. [Stetter & Wulff Chem Ber 93 1366 1960, Beilstein 9 III 4066, 9 IV 2997.]