4-ブロモスチレン
4-ブロモスチレン · 1-ブロモ-4-ビニルベンゼン · p-ブロモスチロール · 4-ブロモ-1-ビニルベンゼン · 1-エテニル-4-ブロモベンゼン · 4-ブロモスチロレン · p-ブロモスチレン · 4-ブロモ-1-エテニルベンゼン
識別子と物理属性
| CAS No. | 2039-82-9 |
|---|---|
| 分子式 | C8H7Br |
| 平均分子量 | 183.04 g/mol |
| 単同位体質量 | 181.97311232 g/mol |
| SMILES | C=Cc1ccc(Br)cc1 |
| InChIKey | WGGLDBIZIQMEGH-UHFFFAOYSA-N |
| PubChem CID | 16263 |
| EC No. | 218-022-6 |
| DTXSID | DTXSID40174330 |
| 現地名 | 4-ブロモスチレン |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 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 | 1 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 90.7 |
| Polymers | Plastics & Rubber -> Styrenes |
| SpringerMaterials Properties | Boiling point |
| Physical Description | Pale yellow liquidmp = 3-6 deg C[Alfa Aesar MSDS] |
| 融点 | 4.5 °C |
| 沸点 | 89 °C16 mm Hg(lit.) |
| 密度 | 1.40 g/mL at 20 °C |
| 屈折率 | n20/D 1.594(lit.) |
| 引火点 | 168 °F |
| 貯蔵条件 | -20°C |
| 溶解度 | エタノール、エーテル、ベンゼンと混和します。 |
| 外観・状態 | 液体 |
| 色 | 薄緑がかった黄色 |
| BRN | 1634204 |
| InChI | InChI=1S/C8H7Br/c1-2-7-3-5-8(9)6-4-7/h2-6H,1H2 |
| InChIKey | WGGLDBIZIQMEGH-UHFFFAOYSA-N |
| SMILES | C1(Br)=CC=C(C=C)C=C1 |
| CAS データベース | 2039-82-9(CAS DataBase Reference) |
| NISTの化学物質情報 | 4-BrC6H4CH=CH2(2039-82-9) |
化学的特性
clear slightly yellow to 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, 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)Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Benzene, 1-bromo-4-ethenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin and strong eye irritant[Alfa Aesar MSDS] See p-Chlorostyrene. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 8 |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29036990 |
| 危険文句（R） | 36/38-36/37/38 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xi |
| hazard_note | Irritant/Keep Cold |
| 安全措置（S） | 26-36-37/39 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
使用
4-Bromostyrene is widely utilized in the synthesis of nitroolefins by alkene cross-metathesis. It plays an important role in the Heck reaction to the synthesis of poly(1,4-phenylenevinylene). It is employed in the structure activity relationships (SAR) study of the chemical and biochemical properties of the vinyl group of styrene. It is also used to investigate the photochemical growth of Br-terminated self-assembled monolayers. It is also involved in the synthesis of silsesquioxanes.
一般的な説明
4-Bromostyrene is a para-halogenated styrene derivative. The proton spectra of 4-bromostyrene exhibits dipolar couplings consistent with planar ground state structures, only if the torsional motion of lowest frequency occurs at about 80cm-1. It undergoes Heck reaction with 2-bromo-6-methoxynaphthalene in the presence of sodium acetate and Hermann′s catalyst in N,N-dimethylacetamide to afford diarylethene.
製法・合成法
純化方法
It polymerises above 75o in the presence of benzoyl peroxide. To purify, if it has not gone to a solid resin, dissolve it in Et2O, dry (MgSO4) and add ca 0.1g of 4-tertbutylcatechol (polymerisation inhibitor) per 100g of bromostyrene. Filter, evaporate this under reduced pressure (use as high a vacuum as possible) and distil the residue. Store it in dark bottles in the presence of the inhibitor (at above concentration). [Overberger & Saunders Org Synth Coll Vol III 204 1955, Beilstein 5 IV 1349.]