ブロモトリメチルシラン
ブロモトリメチルシラン · トリメチルブロモシラン · (トリメチルシリル)ブロミド · トリメチルシリルブロミド · ブロモトリメチルシラン 臭化物 · ブロモトリメチルシラン, 97%, STAB. WITH COPPER POWDER OR SILVER WIRE · TMSBR · TRIMETHYLSILYL BROMIDE
識別子と物理属性
| CAS No. | 2857-97-8 |
|---|---|
| 分子式 | C3H9BrSi |
| 平均分子量 | 153.09 g/mol |
| 単同位体質量 | 151.96568892 g/mol |
| SMILES | C[Si](C)(C)Br |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| PubChem CID | 76113 |
| EC No. | 220-672-0 |
| DTXSID | DTXSID1062671 |
| 現地名 | ブロモトリメチルシラン |
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 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 28.4 |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| 密度 | 1.16 @25 °C1.16 g/mL at 25 °C(lit.) |
| 沸点 | 79 °C @760 [mm Hg]79 °C(lit.) |
| 融点 | -43 °C |
| 屈折率 | n20/D 1.424(lit.) |
| 引火点 | 90 °F |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 分解する |
| 外観・状態 | 液体 |
| 比重 | 1.1725 |
| 色 | 無色透明～黄色 |
| BRN | 1731135 |
| 安定性 | 安定。可燃性。強酸および強力な酸化剤とは相容れない。水または湿った空気と接触すると分解することがある。 |
| InChI | 1S/C3H9BrSi/c1-5(2,3)4/h1-3H3 |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)Br |
| CAS データベース | 2857-97-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Bromotrimethylsilane(2857-97-8) |
| EPAの化学物質情報 | Silane, bromotrimethyl- (2857-97-8) |
化学的特性
Clear yellow liquid
安全性と法規制
| GHS 分類 | DangerH225 (15.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24353Bromotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 2 (15.1%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| 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 2920 8/PG 2 |
| 税関コード | 29310095 |
| 危険文句（R） | 10-34-29-14 |
| 消防法 | 危-4-2-III |
| 危険表示 | C |
| 安全措置（S） | 16-26-36/37/39-45-8 |
| 危険等級 | 3Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 3 - Flammable liquids |
用途
使用
Bromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).
一般的な説明
Bromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.
製法・合成法
製造方法
although many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.
純化方法
Purify it by repeated fractional distillation and store it in sealed ampoules in the dark. [McCusker & Reilly J Am Chem Soc 75 1583 1953.] Also fractionate it through a 15-plate column (0.8 x 32cm packed with 1/16in single turn helices of Pt-Ir wire). [Gilliam et al. J Am Chem Soc 68 1161 1946, Pray et al. J Am Chem Soc 70 433 1948, Beilstein 4 IV 4008.]