tert-Butylsulfinamide, (R)-(+)-
(R)-2-METHYLPROPANE-2-SULFINAMIDE · (R)-TERT-BUTANESULFINAMIDE · (R)-N-tert-Butanesulfinamide · (R)-2-METHYL-2-PROPANESULFINAMIDE · (R)-(+)-TERT-BUTYLSULFINAMIDE · Trityl glycidyl ether · (R)-(+)-TERT-BUTANESULFINAMIDE · DASO-002
식별자 및 물리적 특성
| CAS No. | 196929-78-9 |
|---|---|
| 분자식 | C4H11NOS |
| 평균 분자량 | 121.2 g/mol |
| 단동위원소 질량 | 121.05613497 g/mol |
| SMILES | CC(C)(C)[S@](N)=O |
| InChIKey | CESUXLKAADQNTB-SSDOTTSWSA-N |
| PubChem CID | 10964479 |
| EC No. | 676-338-3 |
| DTXSID | DTXSID40449939 |
화학 및 물리적 성질
| XLogP | 0 |
|---|---|
| 극성 표면적 | 62.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 7 |
| 형식 전하 | 0 |
| 복잡도 | 84.2 |
| 녹는점 | 103-107 °C(lit.) |
| 끓는 점 | 220.0±23.0 °C(Predicted) |
| 밀도 | 0.903 g/mL at 25 °C |
| 굴절률 | 4 ° (C=1, CHCl3) |
| 인화점 | -17℃ |
| 저장 조건 | 2-8°C |
| 용해도 | 클로로포름, 메탄올, 테트라하이드로푸란, 디클로로메탄, 디메틸 설폭사이드 및 대부분의 유기 용매에 용해됩니다. |
| pKa(산도 계수) | 10.11±0.50(Predicted) |
| 물리적 상태 | 가루 |
| 색상 | 흰색, 밝은 분홍색, 밝은 노란색에서 갈색까지 |
| 안정성 | 냉각 |
| InChI | 1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1 |
| InChIKey | CESUXLKAADQNTB-SSDOTTSWSA-N |
| SMILES | CC(C)(C)S(N)=O |
화학적 성질
(R)-(+)-2-Methyl-2-propanesulfinamide is white to light yellow crystal powde
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 33.3% (4 of 12) of reports.WarningH315 (66.7%): 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 12 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Status: Active Update: 04-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30159 |
| Hazard Classes and Categories | Skin Irrit. 2 (66.7%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | No |
| 운송 번호(UN) | UN 2056 3 / PGII |
| 관세 코드 | 29309090 |
| 위험 문구(R) | 11-19-36/37-40-36/37/38 |
| 위험 표시 | Xi,Xn,F |
| 안전 문구(S) | 22-24/25-36/37-26-16-36/37/39 |
| 위험 참고 사항 | Irritant/Keep Cold |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral ligand, which is used in pharmaceutical compositions. Further, it is used in the preparation of beta-chloro sulfinamides in the synthesis of chiral azridines. It is involved in the preparation of organocatalyst for enantioselective reduction of imines. It serves as a reagent for synthesizing chiral amines. In addition to this, it is converted into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones which undergoes iridium-catalyzed asymmetric hydrogenation of olefins.
제조 및 합성 방법
제조 방법
Acetic acid (70 g), R-tert-butylsulfinylhydrazine (42 g), zinc powder (60.5 g) and dichloromethane (150 mL) were added to the reaction flask. The temperature was slowly heated to 35-42 °C . After 16 hours, the filtrate was poured into 70 mL water. Dichloromethane (75 g×5) was added for extraction. Collected the organic phase, added 48% NaOH to adjust ρΗ (7-8). Then added NaCl, the layers were separated and the organic phase was washed with 15 g saturated aqueous solution of sodium chloride. The solution was dried over magnesium sulfate. After filterED, filtrate was concentrated under reduced pressure at 25-30 °C until no slipping. N-heptane was replaced, 28 g mixed solvent of N-heptane and toluene (N-heptane: toluene = 6:1) were added to perform beating at low temperature, filtered to obtain (R)-(+)-2-Methyl-2-propanesulfinamide. Yield=83%