디페닐아세토니트릴
디페닐아세토니트릴 · 다이페닐아세토나이트릴 · 2,2-diphenylacetonitrile · DIPAN · DPAN · dibenzylcyanide · BENZHYDRYL CYANIDE · -Cyanodiphenylmethane
식별자 및 물리적 특성
| CAS No. | 86-29-3 |
|---|---|
| 분자식 | C14H11N |
| 평균 분자량 | 193.24 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 디페닐아세토니트릴 |
화학 및 물리적 성질
| XLogP | 3.2 |
|---|---|
| 극성 표면적 | 23.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 15 |
| 형식 전하 | 0 |
| 복잡도 | 207 |
| 녹는점 | 71-73 °C (lit.) |
| 끓는 점 | 181 °C/12 mmHg (lit.) |
| 밀도 | 1.1061 (rough estimate) |
| 증기압 | 21.3 hPa (190 °C) |
| 굴절률 | 1.5850 (estimate) |
| 인화점 | 120 °C |
| 저장 조건 | Store below +30°C. |
| 용해도 | 불용성 |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 크림색 또는 희미한 노란색 |
| 용해도 | 불용성 |
| 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(분배 계수) | 2.795-3.197 at 25℃ |
| NIST | Benzeneacetonitrile, «alpha»-phenyl-(86-29-3) |
| EPA | Diphenylacetonitrile (86-29-3) |
화학적 성질
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.
안전 및 규제
| 수질 위해 등급(WGK) | 2 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | AL9800000 |
| 독성 | LD50 orally in Rabbit: 3500 mg/kg |
| 관세 코드 | 29269095 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-37/39 |
| 위험 등급 | Aquatic Chronic 2 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
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.
일반 설명
Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride.
제조 및 합성 방법
제조 방법
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.
제조 방법
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.