ジフェニルアセトニトリル
ジフェニルアセトニトリル · ベンジヒドリルシアニド · ジフェナトリル · 2,2-ジフェニルアセトニトリル · ジパン · 2,2-diphenylacetonitrile · DIPAN · DPAN
識別子と物理属性
| CAS No. | 86-29-3 |
|---|---|
| 分子式 | C14H11N |
| 平均分子量 | 193.24 g/mol |
| 単同位体質量 | 193.08914936 g/mol |
| SMILES | N#CC(c1ccccc1)c1ccccc1 |
| InChIKey | NEBPTMCRLHKPOB-UHFFFAOYSA-N |
| PubChem CID | 6837 |
| ChEMBL | CHEMBL3185477 |
| EC No. | 201-662-5 |
| DTXSID | DTXSID4020539 |
| 現地名 | ジフェニルアセトニトリル |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 23.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 2 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 207 |
| 融点 | 71-73 °C (lit.) |
| 沸点 | 181 °C/12 mmHg (lit.) |
| 密度 | 1.1061 (rough estimate) |
| 蒸気圧 | 21.3 hPa (190 °C) |
| 屈折率 | 1.5850 (estimate) |
| 引火点 | 120 °C |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 不溶性 |
| 外観・状態 | 結晶性粉末 |
| 色 | 白色からクリーム色または淡い黄色 |
| Merck | 14,3316 |
| BRN | 1911160 |
| InChI | 1S/C14H11N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H |
| InChIKey | NEBPTMCRLHKPOB-UHFFFAOYSA-N |
| SMILES | N#CC(c1ccccc1)c2ccccc2 |
| LogP（分配係数） | 2.795-3.197 at 25℃ |
| CAS データベース | 86-29-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzeneacetonitrile, «alpha»-phenyl-(86-29-3) |
| EPAの化学物質情報 | Diphenylacetonitrile (86-29-3) |
化学的特性
Diphenylacetonitrile is a white to creamy or faint yellow crystalline powder, Soluble in ethanol, ether. It is obtained by bromination and condensation of phenylacetonitrile. Diphenylacetonitrile is mainly used as an intermediate to manufacture API which deals in treatment of respiratory stimulant. It is used to manufacture APIs like stomach amine, Aminepentamide Sulphate, Diphenoxylate, Diphenylacetaldehyde, Doxapram, Loperamide, Methadone.
安全性と法規制
| 水環境危害等級（WGK） | 2 |
|---|---|
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AL9800000 |
| 毒性 | LD50 orally in Rabbit: 3500 mg/kg |
| 税関コード | 29269095 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (9)-730 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36-37/39 |
| 毒劇物取締法 | 劇物 |
| 危険等級 | Aquatic Chronic 2 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
使用
Mathadone (M225865) impurity. Used in synthesis of methadone, antispasmodics and other pharmaceuticals.Diphenylacetonitrile is used to synthesize isocyanate, which is further prepared into UV paint, PU paint, transparent elastomer and adhesive, etc. In addition, it is also used in polyamide and epoxy resin industries.
一般的な説明
Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride.
製法・合成法
製造方法
In a 100 mL, nitrogen-flushed pear flask was added indium(III) bromide (2.0 mmol, 10 mol %) in CH2Cl2 (40 mL) to give a white suspension. To this at room temperature was added trimethylsilyl cyanide (40 mmol, 2.0 equiv.), followed by dropwise addition of alcohol (20 mmol, 1.0 equiv.) to give a moderate exothermic reaction. The mixture slowly turned clear, and TLC showed mostly the desire product. Saturated NaHCO3 was added and the mixture was concentrated in vacuo to remove the volatiles. The residue was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous layer was extracted one more time with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography on silica gel (5% ethyl acetate/hexanes) to give the desired Diphenylacetonitrile.
製造方法
Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride. Diphenylacetonitrile undergoes anhydrous condensation with ethyl-4-bromo-butyrate. This is followed by its hydrolysis in alkaline medium that is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.
純化方法
Crystallise the nitrile from EtOH or pet ether (b 90-100o). [Beilstein 9 H 674, 9 IV 2505.]