숙신산이미드
석신이미드 · 숙신산이미드 · 숙신이미드 · SI · Pyrrolidine-2,5-dione · 2,5-PYRROLIDINEDIONE · 3,4-Dihydropyrrole-2,5-dione · Lubrizol 2153
식별자 및 물리적 특성
| CAS No. | 123-56-8 |
|---|---|
| 분자식 | C4H5NO2 |
| 평균 분자량 | 99.09 g/mol |
| 단동위원소 질량 | 99.0320284 g/mol |
| SMILES | O=C1CCC(=O)N1 |
| InChIKey | KZNICNPSHKQLFF-UHFFFAOYSA-N |
| PubChem CID | 11439 |
| ChEMBL | CHEMBL275661 |
| ChEBI | CHEBI:9307 |
| EC No. | 204-635-6 |
| DTXSID | DTXSID8051629 |
| 현지명 | 숙신산이미드 |
화학 및 물리적 성질
| XLogP | -1 |
|---|---|
| 극성 표면적 | 46.2 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 7 |
| 형식 전하 | 0 |
| 복잡도 | 105 |
| 물질 분류 | Industrial compound |
| SpringerMaterials Properties | Boiling point |
| 녹는점 | 123-125 °C (lit.) |
| 끓는 점 | 285-290 °C (lit.) |
| 밀도 | 1.41 |
| 증기압 | <1 hPa (50 °C) |
| 굴절률 | 1.4166 (estimate) |
| 인화점 | 201 °C |
| 저장 조건 | Store below +30°C. |
| 용해도 | 330g/L |
| pKa(산도 계수) | 9.6(at 25℃) |
| 물리적 상태 | 분말 또는 플레이크 |
| 색상 | 오프화이트부터 베이지, 라이트 브라운까지 |
| pH | 4-6 (200g/l, H2O) |
| 냄새 | 거의 무취 |
| 용해도 | 물과 에탄올에 용해됩니다. 에테르와 클로로포름에 불용성. |
| Merck | 14,8871 |
| BRN | 108440 |
| InChI | 1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) |
| InChIKey | KZNICNPSHKQLFF-UHFFFAOYSA-N |
| SMILES | O=C1CCC(=O)N1 |
| LogP(분배 계수) | -0.85 at 20℃ |
| NIST | 2,5-Pyrrolidinedione(123-56-8) |
| EPA | Succinimide (123-56-8) |
화학적 성질
white crystalline powder
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 33.2% (120 of 361) of reports.WarningH315 (66.5%): 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 361 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: 2,5-PyrrolidinedioneStatus: Active Update: 18-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/301682,5-Pyrrolidinedione: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (66.5%) |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | WN2200000 |
| 독성 | LD50 orally in rats: 14 g/kg (Melon) |
| 관세 코드 | 29251995 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 22-24/25-36-26-S24/25 |
| 기존화학 물질 | KE-29976 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
Succinimide is used in organic syntheses and in industrial silver plating processes. It is a reagent that is used in the synthesis of Lumiflavin (L473900), which is a toxic photolysis product of vitamin B2 (R415000). Further, it is used to form covalent bonds between proteins, peptides and plastics. In addition to this, it is used as an important raw material for the synthesis of heterocyclic compounds through N-acyliminium cyclizations.
제조 및 합성 방법
제조 방법
To a flask equipped with a dropping funnel, mechanical stirrer, and a 40 cm long side arm of not less than 10 mm inside diameter is added 236 gm (2.0 mole) of succinic acid. The flask is cooled and 270 ml (4.0 moles) of 28% aqueous ammonia is slowly added with stirring. The flask is rapidly heated with an oil bath until 200 ml of water distils. The temperature of the bath is rapidly raised to 275°C. Succinimide starts to distil over the range 275-289°C, to afford 168 gm of crude product which solidifies on cooling. The intermediate fraction, boiling between 102° and 275°C, is redistilled to afford 10.0 gm of crude succinimide, b.p. 275-289°C. The combined product (178 gm) is added to 178 gm of hot ethanol. The solution is cooled, the crystals filtered, washed with 25 ml of cold ethanol, and dried to afford 163-164 gm (82-83%), m.p. 123-125°C. Approximately 4-5 gm of additional product may be obtained by concentrating the mother liquor. Recent Japanese patents suggested inert aprotic solvents such as cyclic amides (e.g., N-methylpyrrolidone, N-acetyl-2-pyrrolidone, DMF, or tet-ramethylurea) and azeotroping solvents (e.g., toluene, 0-xylene, hexane, or pentane) or other high-boiling solvents (e.g., chlorobenzene or chlo-rotoluene) as dehydrating agents for the formation of imides from dibasic acids (e.g., 3- and/or 4) hydroxyphthalic acid with a large variety of diamines including diaminosiloxanes such as bis (3-aminopropyl)-tetra-methylsiloxane.