tert-ブチルジフェニルクロロシラン
tert-ブチルジフェニルクロロシラン · ジフェニル(tert-ブチル)クロロシラン · ジフェニル-tert-ブチルクロロシラン · tert-ブチルクロロジフェニルシラン · クロロtert-ブチルジフェニルシラン · tert-ブチルジフェニルシリルクロリド · 塩化TERT-ブチルジフェニルシリル クロライド ケイ素 塩化物 · TERT‐ブチルクロロジフェニルシラン
識別子と物理属性
| CAS No. | 58479-61-1 |
|---|---|
| 分子式 | C16H19ClSi |
| 平均分子量 | 274.86 g/mol |
| 単同位体質量 | 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 |
| 現地名 | tert-ブチルジフェニルクロロシラン |
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 | 18 |
| 形式電荷 | 0 |
| 複雑度 | 239 |
| 沸点 | 90 °C0.01 mm Hg(lit.) |
| 密度 | 1.057 g/mL at 25 °C(lit.) |
| 屈折率 | n20/D 1.568(lit.) |
| 引火点 | >230 °F |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| 溶解度 | ほとんどの有機溶剤に混和します。反応する |
| 外観・状態 | 液体 |
| 比重 | 1.074 |
| 色 | 無色透明～黄色～微褐色 |
| 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 |
| CAS データベース | 58479-61-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Silane, chloro(1,1-dimethylethyl)diphenyl-(58479-61-1) |
| EPAの化学物質情報 | Silane, chloro(1,1-dimethylethyl)diphenyl- (58479-61-1) |
化学的特性
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.
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 53 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | 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%) |
| F | 10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 2987 8/PG 2 |
| 税関コード | 29310095 |
| 危険文句（R） | 14-34-37-29-20/21/22-40 |
| 消防法 | 危-4-3-III |
| 危険表示 | C,Xi |
| hazard_note | Irritant/Corrosive |
| 安全措置（S） | 26-36/37/39-45-8 |
| 危険等級 | 8Eye Dam. 1Skin Corr. 1BSTOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
用途
用途
アルコールの保護シリル化剤。
使用
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.
製法・合成法
製造方法
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.
純化方法
Purify it by repeated fractional distillaton. It is soluble in DMF and pentane [Hanessian & Lavalee Can J Chem 53 2975 1975, Robl et al. J Med Chem 34 2804 1991]. [Beilstein 4 IV 4076 for tert-butylchlorodimethylsilane.]