安息香酸無水物
安息香酸無水物 · ビス安息香酸無水物 · 無水安息香酸 · ビス(安息香酸)無水物 · 1,3-ジフェニル-2-オキサプロパン-1,3-ジオン · ベンゾイルベンゾアート · 二安息香酸無水物 · 無水安息香酸, 98+%
識別子と物理属性
| CAS No. | 93-97-0 |
|---|---|
| 分子式 | C14H10O3 |
| 平均分子量 | 226.23 g/mol |
| 単同位体質量 | 226.06299418 g/mol |
| SMILES | O=C(OC(=O)c1ccccc1)c1ccccc1 |
| InChIKey | CHIHQLCVLOXUJW-UHFFFAOYSA-N |
| PubChem CID | 7167 |
| ChEMBL | CHEMBL3185530 |
| ChEBI | CHEBI:38815 |
| EC No. | 202-291-1 |
| DTXSID | DTXSID1029122 |
| 現地名 | 安息香酸無水物 |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 43.4 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 4 |
| 重原子数 | 17 |
| 形式電荷 | 0 |
| 複雑度 | 245 |
| 物質分類 | Other Classes -> Acid Anhydrides, Other |
| SpringerMaterials Properties | Boiling point |
| Exact Mass | 226.062994177 Da |
| Molecular Weight | 226.23 g/mol |
| Monoisotopic Mass | 226.062994177 Da |
| Physical Description | Solid[Merck Index] White crystalline powderOdorless[Alfa Aesar MSDS] |
| Compound Is Canonicalized | Yes |
| 融点 | 38-42 °C(lit.) |
| 沸点 | 360 °C |
| 密度 | 1.199 g/mL at 25 °C(lit.) |
| 屈折率 | nD15 1.57665 |
| 引火点 | >230 °F |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| 溶解度 | 0.01g/l (実験的) |
| 外観・状態 | 結晶または結晶性粉末 |
| 色 | 白～ほぼ白 |
| Merck | 14,1092 |
| BRN | 516726 |
| ヘンリー定数 | 7.0×100 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| InChI | 1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H |
| InChIKey | CHIHQLCVLOXUJW-UHFFFAOYSA-N |
| SMILES | O=C(OC(=O)c1ccccc1)c2ccccc2 |
| CAS データベース | 93-97-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, anhydride(93-97-0) |
| EPAの化学物質情報 | Benzoic anhydride (93-97-0) |
化学的特性
white to almost white crystals or crystalline
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 42.7% (41 of 96) of reports.DangerH315 (57.3%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 96 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzoic acid, anhydrideStatus: Active Update: 24-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24998Benzoic acid, anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Reacts with waterA skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (57.3%) |
| F | 10-21 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29163900 |
| 危険文句（R） | 37/38-41-36/37/38 |
| 化審法 | (3)-3516 |
| 危険表示 | Xi |
| 安全措置（S） | 26-39-37/39 |
| 危険等級 | Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
用途
解説
安息香酸無水物，結晶．融点42 ℃，沸点360 ℃．d1541.99．n15D1.5766．エタノール，エーテルなどに可溶．無水酢酸よりも反応性は劣るが，ヒドロキシ基やアミノ基のベンゾイル化剤として用いられる．森北出版「化学辞典（第2版）
使用
Benzoic Anhydride is the more active analogue of benzoic acid formed via dehydration. Benzoic Anhydride is used in the synthesis of a wide range of organic compounds including some dyes. Benzoic Anhyd ride is also used as an arylation agent in the Heck reaction.
一般的な説明
Benzoic anhydride undergoes Friedel-Crafts acylation reaction with benzene over various ion-exchanged heteropoly acids to yield benzophenone.
製法・合成法
製造方法
To a flask containing 14.0 gm (0.1 mole) of benzoyl chloride and equipped with a stirrer is added 40 ml of dry dioxane and it is cooled to 5°C.Then 10 ml (0.1 mole) of dry pyridine is rapidly added at 5-10°C followed by 1.0 ml (0.056 mole) of water. After stirring for 10-15 min at 0-5°C, the reaction mixture is then poured into a mixture of 75 ml of cone, hydrochloric acid, 75 gm of cracked ice, and 350 ml of water. The product is filtered, washed first for 1 min with a cold 5% solution of sodium bicarbonate and then with water. The product is dried to afford 11.0 gm (97%), m.p. 43°C (recrystallized from a mixture of ether-petroleum ether).
純化方法
Free it from benzoic acid by washing with NaHCO3, then water, and drying. Crystallise it from *benzene (0.5mL/g) by adding just enough pet ether (b 40-60o) to cause cloudiness, then cool in ice. It can be distilled at 210-220o/20mm. [Beilstein 19 IV 550.]