4'-ブロモアセトアニリド
4'-ブロモアセトアニリド · アンチセプシン · ブロモアニリド · N-(4-ブロモフェニル)アセトアミド · ブロモアンチフェブリン · N-アセチル-4-ブロモアニリン · N-(p-ブロモフェニル)アセトアミド · 4-ブロモ-1-アセチルアミノベンゼン
識別子と物理属性
| CAS No. | 103-88-8 |
|---|---|
| 分子式 | C8H8BrNO |
| 平均分子量 | 214.06 g/mol |
| 単同位体質量 | 212.97892598 g/mol |
| SMILES | CC(=O)Nc1ccc(Br)cc1 |
| InChIKey | MSLICLMCQYQNPK-UHFFFAOYSA-N |
| PubChem CID | 7683 |
| ChEMBL | CHEMBL59019 |
| EC No. | 203-154-9 |
| DTXSID | DTXSID6059283 |
| 現地名 | 4'-ブロモアセトアニリド |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 29.1 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 141 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | 2.14 |
| 融点 | 165-169 °C(lit.) |
| 沸点 | 353.4°C (estimate) |
| 密度 | 1.72 |
| 屈折率 | 1.6120 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | アルコール：適度に溶ける不溶性 |
| 外観・状態 | 結晶性粉末または結晶 |
| pKa（酸解離定数） | 14.25±0.70(Predicted) |
| 色 | ホワイトからベージュまたはライトグレー |
| Merck | 14,1399 |
| BRN | 2208091 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | 1S/C8H8BrNO/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,1H3,(H,10,11) |
| InChIKey | MSLICLMCQYQNPK-UHFFFAOYSA-N |
| SMILES | CC(=O)Nc1ccc(Br)cc1 |
| CAS データベース | 103-88-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetamide, N-(4-bromophenyl)-(103-88-8) |
| EPAの化学物質情報 | Acetamide, N-(4-bromophenyl)- (103-88-8) |
化学的特性
4'-Bromoacetanilide is a white to light beige crystalline solid with a melting point of 168°C and a relative density of 1.717. It is soluble in benzene, chloroform, and ethyl acetate, slightly soluble in alcohol and hot water, and insoluble in cold water. This compound can be prepared by brominating acetanilide and is commonly used as an intermediate in organic synthesis.
安全性と法規制
| GHS 分類 | WarningH315 (97.9%): 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 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Acetamide, N-(4-bromophenyl)-Acetamide, N-(4-bromophenyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (97.9%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AD9625000 |
| 輸送番号（UN） | 2811 |
| 毒性 | mouse,LD50,intraperitoneal,250mg/kg (250mg/kg),National Technical Information Service. Vol. AD277-689, |
| 税関コード | 29242998 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (3)-196 |
| 危険表示 | Xi |
| hazard_note | Irritant |
| 安全措置（S） | 26-36 |
| 危険等級 | 6.1(b) |
| 包装等級 | III |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
4'-Bromoacetanilide is used as an internal standard for phenylurea and the respective metabolic products in oysters. It has also been used as a reagent in the production of a new ligand to form a coordination compex between gadolinium(III) and T=titanium(IV) oxide. It was used in the synthesis of new ligand for anchoring Gd(III) chelates onto TiO2 surface.
製法・合成法
製造方法
Preparation of 4'-Bromoacetanilide from Acetanilide. Principle: Aromatic compounds can be conveniently brominated by the use of brominating agent, which is normally a solution of bromine in acetic acid. Bromination of activated aromatic compounds usually give 2, 4, 6-tribromo derivatives while moderately activating group like anilide give preferably the para bromo product. Reaction: Procedure: Dissolve 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 2.5 ml bromine solution in acetic acid (25% w/v). Shake the mixture for 1 h. After 1 h, pour the mixture on to crushed ice (20 g) with stirring. Filter the separated product and wash with cold water. Dry the product, record the practical yield and re-crystallize it. Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC (using toluene as a solvent).
純化方法
Crystallise the anilide from aqueous MeOH or EtOH. Purify it by zone refining. [Beilstein 12 IV 1504.]