부틸디페닐클로로실란
부틸디페닐클로로실란 · 실란,클로로(1,1-디메틸에틸)디페닐- · TERT-뷰틸클로로다이페닐실레인 · TBDPSCl · TBDPS · TBDPSCI · TBDPCL · TBDP
식별자 및 물리적 특성
| CAS No. | 58479-61-1 |
|---|---|
| 분자식 | C16H19ClSi |
| 평균 분자량 | 274.86 g/mol |
| 단동위원소 질량 | 274.09445482 g/mol |
| SMILES | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1 |
| InChIKey | MHYGQXWCZAYSLJ-UHFFFAOYSA-N |
| PubChem CID | 94078 |
| EC No. | 261-282-0 |
| DTXSID | DTXSID5069259 |
| 현지명 | 부틸디페닐클로로실란 |
화학 및 물리적 성질
| 극성 표면적 | 0 |
|---|---|
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 18 |
| 형식 전하 | 0 |
| 복잡도 | 239 |
| 끓는 점 | 90 °C0.01 mm Hg(lit.) |
| 밀도 | 1.057 g/mL at 25 °C(lit.) |
| 굴절률 | n20/D 1.568(lit.) |
| 인화점 | >230 °F |
| 저장 조건 | Inert atmosphere,2-8°C |
| 용해도 | 대부분의 유기용매에 섞인다. |
| 물리적 상태 | 액체 |
| 비중 | 1.074 |
| 색상 | 투명한 무색~노란색 또는 약간 갈색 |
| 용해도 | 물과 반응 |
| BRN | 644023 |
| InChI | 1S/C16H19ClSi/c1-16(2,3)18(17,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13H,1-3H3 |
| InChIKey | MHYGQXWCZAYSLJ-UHFFFAOYSA-N |
| SMILES | CC(C)(C)[Si](Cl)(c1ccccc1)c2ccccc2 |
| NIST | Silane, chloro(1,1-dimethylethyl)diphenyl-(58479-61-1) |
| EPA | Silane, chloro(1,1-dimethylethyl)diphenyl- (58479-61-1) |
화학적 성질
Tert-Butylchlorodiphenylsilane is a colorless to pale brown oily liquid with pungent odor, may be used as silylating agent for derivatization of alcohols, ketones, carboxylic acids, amines, amides and mercaptanes selectively into functional groups in different sterical environments.
안전 및 규제
| GHS 분류 | DangerH314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: Silane, chloro(1,1-dimethylethyl)diphenyl-Silane, chloro(1,1-dimethylethyl)diphenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Corr. 1 (100%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 2987 8/PG 2 |
| 관세 코드 | 29310095 |
| 위험 문구(R) | 14-34-37-29-20/21/22-40 |
| 위험 표시 | C,Xi |
| 안전 문구(S) | 26-36/37/39-45-8 |
| 포장분류 | II |
| 위험 등급 | 8Eye Dam. 1Skin Corr. 1BSTOT SE 3 |
| F 고인화성물질 | 10 |
| 위험 참고 사항 | Irritant/Corrosive |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
용도
용도
Several newmethods have been developed for using the reagent to protect primary and secondary alcohols as their TBDPS ethers. In the presence of ammonium nitrate or ammonium perchlorate, reaction between TBDPS-Cl and a primary alcohol, such as benzyl alcohol, in DMF provided excellent yields of the corresponding silyl ethers in just 15 min (eq 1).19 When silver nitrate was used as promoter, the reactions gave inferior yields under otherwise identical conditions.When TBDPS-Cl is used to react with hemiacetals, it converts hemiacetals into ring-opened silyl ether carbonyl compounds, instead of mixed acetals.Presumably, the sizable TBDPS group presents too much steric hindrance for the formation of the corresponding mixed silyl acetals.
제조 및 합성 방법
제조 방법
a dry 1 L, three-necked round bottomed flask is equipped with a magnetic stirring bar, a 500mL equalizing dropping funnel fitted with a rubber septum, a reflux condenser, and nitrogen inlet tube. The flask is flushed with nitrogen, then charged with 127 g (0.5 mol) of diphenyldichlorosilane in 300mL of redistilled pentane. A solution of tbutyllithium in pentane (500 mL, 0.55 mol), is transferred under nitrogen pressure to the dropping funnel using a stainless steel, double-tip transfer needle. This solution is slowly added to the contents of the flask and when the addition is complete, the mixture is refluxed 30 h under nitrogen with stirring. The suspension is allowed to cool to rt, the precipitated lithium chloride is rapidly filtered through a pad of Celite, and the latter is washed with 200mL of pentane. The solvent is removed by evaporation, and the colorless residue is distilled through a short (10 cm), Vigreux column, to give 125–132 g of the colorless title compound.