3'-Chloropropiophenone
MCPP · M-CHLOROPROPIOPHENONE · 1-(3-chlorophenyl)propan-1-one · 3&priMe · 3-chlorophenone · 3'-chloroacetone · M-ChloroProiophenone · 3'-Chloropropiopheno
식별자 및 물리적 특성
| CAS No. | 34841-35-5 |
|---|---|
| 분자식 | C9H9ClO |
| 평균 분자량 | 168.62 g/mol |
| 단동위원소 질량 | 168.03419259 g/mol |
| SMILES | CCC(=O)c1cccc(Cl)c1 |
| InChIKey | PQWGFUFROKIJBO-UHFFFAOYSA-N |
| PubChem CID | 587128 |
| ChEMBL | CHEMBL2251583 |
| EC No. | 252-242-3 |
| DTXSID | DTXSID1049277 |
화학 및 물리적 성질
| XLogP | 3 |
|---|---|
| 극성 표면적 | 17.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 144 |
| 녹는점 | 45-47 °C(lit.) |
| 끓는 점 | 124 °C14 mm Hg(lit.) |
| 밀도 | 1.1115 (rough estimate) |
| 굴절률 | 1.5350 (estimate) |
| 인화점 | >230 °F |
| 저장 조건 | Sealed in dry,Room Temperature |
| 용해도 | 메탄올에 용해됩니다. |
| 물리적 상태 | 결정질 고체 |
| 색상 | 흰색에서 밝은 노란색 |
| InChI | InChI=1S/C9H9ClO/c1-2-9(11)7-4-3-5-8(10)6-7/h3-6H,2H2,1H3 |
| InChIKey | PQWGFUFROKIJBO-UHFFFAOYSA-N |
| SMILES | C(C1=CC=CC(Cl)=C1)(=O)CC |
| LogP(분배 계수) | 3.041 |
화학적 성질
WHITE TO LIGHT YELLOW CRYSTALLINE SOLID
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 81.8% (9 of 11) of all reports.WarningH315 (18.2%): 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 11 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Status: Active Update: 20-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11873 |
| Hazard Classes and Categories | Skin Irrit. 2 (18.2%) |
| 수질 위해 등급(WGK) | 3 |
| 관세 코드 | 29147000 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 37/39-26-24/25 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Influence of solvents and temperature on the yield and enantioselectivity of the phenylation of 3′-chloropropiophenone has been investigated.
용도
3'-Chloropropiophenone is a reagent used in the vinylation, alkylation and dienylation of ketones. It is also used in the preparation of thizaine derivatives that show antibacterial activity.
일반 설명
3'-Chloropropiophenone is a key intermediate in drug synthesis, mainly used to prepare various pharmaceutical compounds such as the antidepressant bupropion, dapoxetine, and the anti-AIDS drug maraviro.
제조 및 합성 방법
제조 방법
4.86 g (0.2 mol) of magnesium turnings, 30 ml of dry diethyl ether and a grain of iodine are placed in a one liter three-necked round-bottomed flask equipped with a condenser, a calcium chloride drying tube, a pressure equalizing funnel and a magnetic stirrer; the flask is purged with nitrogen, and 21.8 g (0.2 mol) of ethyl bromide in 30 ml of dry diethyl ether are then added. The mixture is then heated under reflux for one hour and left to cool. At ambient temperature, 16.51 g (0.12 mol) of 3-chlorobenzonitrile in 70 ml of dry diethyl ether are then added. A copious precipitate forms. The mixture is stirred overnight at ambient temperture and then cooled in an ice bath and hydrolysed by slowly adding 50 ml of water and then about 100 ml of 6N hydrochloric acid until the pH is acid. The mixture is stirred for one and a half hours and then extracted with ethyl acetate. The organic extract is then washed twice with water, dried and concentrated on a rotary evaporator. This gives 26 g of an orange oil, which is concentrated in vacuo to give about 18.2 g of ochre crystals of 3'-chloropropiophenone melting at about 40° C.Literature source US04690931