1,2-Bis(chlorodimethylsilyl)ethane
1,1,4,4-TETRAMETHYL-1,4-DICHLORODISILYLETHYLENE · 1,2-Bis(chlorodimethylsilyl) · chloro[2-(chlorodimethylsilyl)ethyl]dimethylsilane · DK065 · DK525 · STABASE · SILANE BM2E · [-CH2Si(CH3)2Cl]2
식별자 및 물리적 특성
| CAS No. | 13528-93-3 |
|---|---|
| 분자식 | C6H16Cl2Si2 |
| 평균 분자량 | 215.26 g/mol |
| 단동위원소 질량 | 214.016759 g/mol |
| SMILES | C[Si](C)(Cl)CC[Si](C)(C)Cl |
| InChIKey | VGQOKOYKFDUPPJ-UHFFFAOYSA-N |
| PubChem CID | 83552 |
| EC No. | 236-871-0 |
| DTXSID | DTXSID9065520 |
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 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 98 |
| 녹는점 | 35-38 °C (lit.) |
| 끓는 점 | 198 °C/734 mmHg (lit.) |
| 밀도 | 0.99 |
| 인화점 | 155 °F |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 물리적 상태 | 저융점 고체 |
| 색상 | 투명한 |
| 용해도 | 물과 반응합니다. |
| BRN | 1920141 |
| InChI | 1S/C6H16Cl2Si2/c1-9(2,7)5-6-10(3,4)8/h5-6H2,1-4H3 |
| InChIKey | VGQOKOYKFDUPPJ-UHFFFAOYSA-N |
| SMILES | C[Si](C)(Cl)CC[Si](C)(C)Cl |
| EPA | Silane, 1,2-ethanediylbis[chlorodimethyl- (13528-93-3) |
화학적 성질
transparent low melting solid
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 46 reports by companies from 5 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 규제 정보 | Chemical: Silane, 1,2-ethanediylbis[chlorodimethyl- |
| Hazard Classes and Categories | Skin Corr. 1B (100%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 3261 8/PG 2 |
| 관세 코드 | 29319000 |
| 위험 문구(R) | 34-10 |
| 위험 표시 | C |
| 안전 문구(S) | 26-28-36/37/39-45-16 |
| 포장분류 | III |
| 위험 등급 | 8Skin Corr. 1B |
| F 고인화성물질 | 10-21 |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
용도
용도
1,2-Bis(chlorodimethylsilyl)ethane can be used as a reagent for the protection of primary amines as their tetramethyldisilylazacyclopentane or Stabase adducts; used in combination with zinc to form organozinc carbenoids; electrophilic silylating reagent.Protection of Primary Amines.Few protecting groups exist for the N,N-diprotection of primary amines. The tetramethyldisilylazacyclopentane or Stabase adduct (3) is particularly attractive for this purpose due to its ease of preparation, base stability and facile removal. This cyclic disilane is easily prepared (eq 1) from the commercially available title reagent (1).For primary amines with pKa values between 10 and 11, typical reaction conditions involve the treatment of a dichloromethane solution of the amine with (1) in the presence of two equivalents of triethylamine at room temperature. Subsequent workup with aqueous dihydrogen phosphate provides (3) in excellent yields.1 Stabase adducts are quite stable to strongly basic conditions such as n-butyllithium and s-butyllithium (at 25°C), lithium diisopropylamide, and Grignard reagents making it a superb candidate for use in the alkylation of substrates bearing a primary amine. For example, protected amino acid derivatives are easily alkylated (eq 2).After formation of the lithium enolate of the protected ethyl glycinate (4) under standard conditions, exposure to various alkyl halides or aldehydes yields alkylation products such as (5).