디-터어트-뷰틸실릴 비스(트리플루오로메탄설포네이트)
디-터어트-뷰틸실릴비스(트리플루오로메탄설포네이트) · 디-터어트-뷰틸실릴비스(트리플루오로메탄설포네이트)(DI-tert-BUTYLSILYLBIS(TRIFLUOR... · 1,1,1-트리플루오로메탄술폰산 비스(1,1-디메틸에틸)[[(트리플루오로메틸) 술포닐]옥시]실릴 · Di-tert-butylsilanediyl bis(trifluoroMethanesulfonate) · BIS(TRIFLUOROMETHANESULFONATE) · DI-TERT-BUTYLBIS(TRIFLUOROMETHANESULFONYLOXY)SILANE · DI-T-BUTYLSILYLBIS(TRIFLUOROMETHANESULFONATE) · DI-TERT-BUTYLSILYL DITRIFLATE
식별자 및 물리적 특성
| CAS No. | 85272-31-7 |
|---|---|
| 분자식 | C10H18F6O6S2Si |
| 평균 분자량 | 440.456 g/mol |
| 단동위원소 질량 | 440.02182615 g/mol |
| SMILES | CC(C)(C)[Si](OS(=O)(=O)C(F)(F)F)(OS(=O)(=O)C(F)(F)F)C(C)(C)C |
| InChIKey | HUHKPYLEVGCJTG-UHFFFAOYSA-N |
| PubChem CID | 545813 |
| EC No. | 680-172-7 |
| DTXSID | DTXSID50337994 |
| 현지명 | 디-터어트-뷰틸실릴 비스(트리플루오로메탄설포네이트) |
화학 및 물리적 성질
| 끓는 점 | 73-75 °C/0.35 mmHg (lit.) |
|---|---|
| 밀도 | 1.352 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.398(lit.) |
| 인화점 | 195 °F |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 용해도 | 가장 일반적인 유기 용매인 Sol입니다. |
| 물리적 상태 | 기름 |
| 색상 | 맑은 연한 노란색 |
| 비중 | 1.358 |
| BRN | 3569211 |
| 안정성 | 수분에 민감한 |
| InChI | InChI=1S/C10H18F6O6S2Si/c1-7(2,3)25(8(4,5)6,21-23(17,18)9(11,12)13)22-24(19,20)10(14,15)16/h1-6H3 |
| InChIKey | HUHKPYLEVGCJTG-UHFFFAOYSA-N |
| SMILES | C(F)(F)(F)S(O[Si](C(C)(C)C)(C(C)(C)C)OS(C(F)(F)F)(=O)=O)(=O)=O |
화학적 성질
Colorless to yellow liquid
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | No |
| 운송 번호(UN) | UN 3265 8/PG 2 |
| 관세 코드 | 29319090 |
| 위험 문구(R) | 34 |
| 위험 표시 | C |
| 안전 문구(S) | 26-36/37/39-45 |
| 포장분류 | III |
| 위험 등급 | 8Skin Corr. 1B |
| F 고인화성물질 | 10-21 |
| 위험 참고 사항 | Corrosive |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
| 함량 및 규제정보 | 물질구분: 유독물질혼합물(제품)함량정보: 1,1,1-트리플루오로메탄술폰산 비스(1,1-디메틸에틸)[[(트리플루오로메틸) 술포닐]옥시]실릴 및 이를 5% 이상 함유한 혼합물 |
| 유해화학물질 필터링 | 2018-1-876(신규화학물질) |
용도
용도
Di-t-butylsilyl bis(trifluoromethanesulfonate) is a reagent for the selective protection of polyhydroxy compounds. This reagent reacts with 1,2-, 1,3-, and 1,4-diols under mild conditions to give the corresponding dialkylsilylene derivatives in high yield (0–50°C, 79–96%). Deprotection is conveniently achieved by using aqueous hydrofluoric acid in acetonitrile (eq 1).Unlike di-t-butyldichlorosilane, this reagent reacts with hindered alcohols. Even pinacol reacts to give the silylene derivative (100°C, 24 h, 70%). Di-t-butylsilylene derivatives of 1,2-diols are more reactive than those of 1,3- and 1,4-diols and undergo rapid hydrolysis (5 min) in THF/H2O at pH 10, while the 1,3- and 1,4- derivatives are unaffected at pH 4–10 (22°C) for several hours. This protecting group is stable under the conditions of PDC oxidation of alcohols (CH2Cl2, 25C, 27 h) and tosylation of alcohols (pyridine, 25°C, 27 h).The reagent has seen limited use for the protection of alcohols but has been used to protect nucleosides (eq 2).The procedure consists of sequential addition of the ditriflate and triethylamine to the nucleoside in DMF. The choice of solvent is critical.
제조 및 합성 방법
제조 방법
by the treatment of di-t-butylchlorosilane with trifluoromethanesulfonic acid, followed by distillation (71% yield).