1,2-ビス(クロロジメチルシリル)エタン
1,2-ビス(クロロジメチルシリル)エタン · 1,2-エタンジイルビス(クロロジメチルシラン) · エチレンビス(ジメチルクロロシラン) · エチレンビス(クロロジメチルシラン) · 1,2-ビス(ジメチルクロロシリル)エタン · 1,2‐ビス(クロロジメチルシリル)エタン · クロロ[2-(クロロジメチルシリル)エチル]ジメチルシラン · 1,1,4,4-TETRAMETHYL-1,4-DICHLORODISILYLETHYLENE
識別子と物理属性
| CAS No. | 13528-93-3 |
|---|---|
| 分子式 | C6H16Cl2Si2 |
| 平均分子量 | 215.26 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 1,2-ビス(クロロジメチルシリル)エタン |
化学・物理的性質
| 極性表面積 | 0 |
|---|---|
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 3 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 98 |
| 融点 | 35-38 °C (lit.) |
| 沸点 | 198 °C/734 mmHg (lit.) |
| 密度 | 0.99 |
| 引火点 | 155 °F |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 外観・状態 | 低融点固体 |
| 色 | トランスペアレント |
| 溶解度 | 水と反応する。 |
| 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 |
| CAS データベース | 13528-93-3(CAS DataBase Reference) |
| EPAの化学物質情報 | Silane, 1,2-ethanediylbis[chlorodimethyl- (13528-93-3) |
化学的特性
transparent low melting solid
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | Chemical: Silane, 1,2-ethanediylbis[chlorodimethyl- |
| Hazard Classes and Categories | Skin Corr. 1B (100%) |
| F | 10-21 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 3261 8/PG 2 |
| 税関コード | 29319000 |
| 危険文句（R） | 34-10 |
| 消防法 | 危-4-2-III |
| 危険表示 | C |
| 安全措置（S） | 26-28-36/37/39-45-16 |
| 危険等級 | 8Skin Corr. 1B |
| 包装等級 | III |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
用途
使用
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).