2-トリメチルシリル-1,3-ジチアン
2-トリメチルシリル-1,3-ジチアン · (1,3-ジチアン-2-イル)トリメチルシラン · 1,3-ジチアン-2-イルトリメチルシラン · 2-(トリメチルシリル)-1,3-ジチアン · 2-TRIMETHYLSILYL-1,3-DITHIANE · 1,3-DITHIAN-2-YLTRIMETHYLSILANE · 1,3-Dithiane-2-yltrimethylsilane · 2-TRIMETHYLSILYL-1,3-DITHIANE 97%
識別子と物理属性
| CAS No. | 13411-42-2 |
|---|---|
| 分子式 | C7H16S2Si |
| 平均分子量 | 192.4 g/mol |
| 単同位体質量 | 192.04626904 g/mol |
| SMILES | C[Si](C)(C)C1SCCCS1 |
| InChIKey | BTTUMVHWIAXYPJ-UHFFFAOYSA-N |
| PubChem CID | 83413 |
| EC No. | 236-504-4 |
| DTXSID | DTXSID70158542 |
| 現地名 | 2-トリメチルシリル-1,3-ジチアン |
化学・物理的性質
| 極性表面積 | 50.6 |
|---|---|
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 103 |
| SpringerMaterials Properties | Chemical shift |
| 沸点 | 54-55 °C0.17 mm Hg(lit.) |
| 密度 | 1.014 g/mL at 25 °C(lit.) |
| 屈折率 | n20/D 1.533(lit.) |
| 引火点 | 205 °F |
| 貯蔵条件 | 2-8°C |
| 溶解度 | インソル H2Oゾル有機溶剤。 |
| 外観・状態 | clear liquid |
| 色 | Colorless to Light yellow to Light orange |
| 比重 | 1.014 |
| BRN | 1616463 |
| InChI | 1S/C7H16S2Si/c1-10(2,3)7-8-5-4-6-9-7/h7H,4-6H2,1-3H3 |
| InChIKey | BTTUMVHWIAXYPJ-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)C1SCCCS1 |
| CAS データベース | 13411-42-2(CAS DataBase Reference) |
化学的特性
CLEAR COLORLESS TO SLIGHTLY YELLOW LIQUID
安全性と法規制
| GHS 分類 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 13 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | No |
| 輸送番号（UN） | 3334 |
| 税関コード | 2934.99.9001 |
| 消防法 | 危-4-3-III |
| 安全措置（S） | 23-24/25 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
使用
2-Trimethylsilyl-1,3-dithiane is the precursor of dithioketene acetals which are good substrates for both cationic and anionic cyclization processes; the anion reacts with unsaturated ketones and aldehydes to give vinyl dithioketene acetals that can be used as dienes or for the preparation of substituted α,β-unsaturated alkyl ketones; alkylation of the anion provides a general synthesis of acylsilanes. It participates the following reactions: Thioketene Acetals, Cationic and Anionic Cyclizations, Unsaturated Dithioketene Acetals, Acylsilanes, Multicomponent Linchpin Reactions, Formation of Bis(acylsilanes) etc.
一般的な説明
2-(Trimethylsilyl)-1,3-dithiane participates in Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines. It undergoes novel diazo transfer reaction with tosyl azide in hexamethylphosphoramide-THF to yield 2-diazo-1,3-dithiane, which on decomposition yields formal carbene adducts. It is a versatile acyl anion equivalent.
製法・合成法
製造方法
2-Trimethylsilyl-1,3-dithiane is prepared by alkylation of 2-lithio-1,3- dithiane with chlorotrimethylsilane (eq 1).
純化方法
Fractionally distil the dithiane through an efficient column and collect the fractions that have the correct NMR and IR spectra. 1H NMR (CCl4) 6.36 (SiMe3), 9.87 (SCHS) and dithiane H at 7 and 8 (ratio 1:9:4:2) from Me4Si; UV 244nm ( 711), sh 227nm ( 800). [Corey et al. J Am Chem Soc 89 max 434 1967.]