나프톨[2,3-c]퓨란-1,3-다이온
나프톨[2,3-c]퓨란-1,3-다이온 · 2,3-나프탈렌디카복실산무수물 · naphtho[2,3-c]furan-1,3-dione · EA253 · 2,3-NAPHTHALI · 2,3-NAPHTHALIC ANHYDRIDE · benzo[f][2]benzofuran-1,3-dione · 2,3-Napthalenedicarboxycanhydride
![나프톨[2,3-c]퓨란-1,3-다이온 분자 구조식](/img/chemical/69743.png)
식별자 및 물리적 특성
| CAS No. | 716-39-2 |
|---|---|
| 분자식 | C12H6O3 |
| 평균 분자량 | 198.17 g/mol |
| 단동위원소 질량 | 198.03169405 g/mol |
| SMILES | O=C1OC(=O)c2cc3ccccc3cc21 |
| InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
| PubChem CID | 69743 |
| EC No. | 211-936-6 |
| DTXSID | DTXSID9061049 |
| 현지명 | 나프톨[2,3-c]퓨란-1,3-다이온 |
화학 및 물리적 성질
| XLogP | 2.5 |
|---|---|
| 극성 표면적 | 43.4 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 15 |
| 형식 전하 | 0 |
| 복잡도 | 280 |
| 녹는점 | 246 °C |
| 끓는 점 | 275-280 °C(Press: 100 Torr) |
| 밀도 | 1.449±0.06 g/cm3(Predicted) |
| 저장 조건 | under inert gas (nitrogen or Argon) at 2-8°C |
| 용해도 | 클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨) |
| 물리적 상태 | 고체 |
| 색상 | 페일베이지 |
| 안정성 | 수분에 민감한 |
| 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 | Naphtho[2,3-c]furan-1,3-dione (716-39-2) |
안전 및 규제
| GHS 분류 | 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 등재 상태 | TSCA listed |
| 관세 코드 | 2917.39.7000 |
| 안전 문구(S) | 22-24/25 |
| 기존화학 물질 | 2003-3-2439 |
용도
개요
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.
용도
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.
제조 및 합성 방법
제조 방법
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%.