2,3-ナフタレンジカルボン酸無水物
2,3-ナフタレンジカルボン酸無水物 · ナフト[2,3-c]フラン-1,3-ジオン · 1,3-ジヒドロナフト[2,3-c]フラン-1,3-ジオン · ナフタレン-2,3-ジカルボン酸無水物 · 2,3-ナフタレン二カルボン酸無水物 · naphtho[2,3-c]furan-1,3-dione · EA253 · 2,3-NAPHTHALI
識別子と物理属性
| CAS No. | 716-39-2 |
|---|---|
| 分子式 | C12H6O3 |
| 平均分子量 | 198.17 g/mol |
| 単同位体質量 | 198.03169405 g/mol |
| SMILES | O=C1OC(=O)c2cc3ccccc3cc21 |
| InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
| PubChem CID | 69743 |
| EC No. | 211-936-6 |
| DTXSID | DTXSID9061049 |
| 現地名 | 2,3-ナフタレンジカルボン酸無水物 |
化学・物理的性質
| XLogP | 2.5 |
|---|---|
| 極性表面積 | 43.4 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 280 |
| 融点 | 246 °C |
| 沸点 | 275-280 °C(Press: 100 Torr) |
| 密度 | 1.449±0.06 g/cm3(Predicted) |
| 貯蔵条件 | under inert gas (nitrogen or Argon) at 2-8°C |
| 溶解度 | クロロホルム（微量）、酢酸エチル（微量） |
| 外観・状態 | 個体 |
| 色 | ペールベージュ |
| 安定性 | 湿気に敏感 |
| InChI | InChI=1S/C12H6O3/c13-11-9-5-7-3-1-2-4-8(7)6-10(9)12(14)15-11/h1-6H |
| InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
| SMILES | O1C(=O)C2=CC3C(C=C2C1=O)=CC=CC=3 |
| EPAの化学物質情報 | Naphtho[2,3-c]furan-1,3-dione (716-39-2) |
安全性と法規制
| GHS 分類 | WarningH315 (100%): 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 2917.39.7000 |
| 安全措置（S） | 22-24/25 |
用途
説明
A few years ago, the product was still synthesized from the corresponding diacid, but in recent years, it has been difficult to find the shadow of the diacid in the market, and the sales of this product have been repeatedly restricted, resulting in high prices.
使用
2,3-Naphthalic anhydride is used as a reagent to synthesize analogues of Thalidomide (T338850), an inhibitor of tumour necrosis factor that was once abandoned because it caused birth defects, but is currently used as an inhibitor of angiogenesis in patients with multiple myeloma.
製法・合成法
製造方法
Add anhydrous tetrahydrofuran (its mass ratio to maleic anhydride is 1.5:1), cat-1 (0.05 mole), maleic anhydride (1 mole), and o-phthalaldehyde (1.5 mole) to the reactor. After adding triethylamine (5 moles), adjust the temperature below -40°C. Silicon tetrachloride (4 moles) was added dropwise to the reaction system and the reaction was placed at -40 °C for 4 h. The mixture was heated to reflux for 20 h. After the end of the reaction, concentrating the solution to a certain concentration with diatomaceous earth filtration. A light yellow solid, namely 2,3-Naphthalenedicarboxylic Anhydride, is obtained by precipitation, filtration, recrystallization and drying. Its yield reaches 88%.