Name | 2-Chloro-1-phenyl-1-propanone |
Synonyms | 2-Chloropropiophenone 2-CHLOROPROPIOPHENONE 2-CHLORO-1-PHENYL-1-PROPANONE 2-Chloro-1-phenyl-1-propanone 2-chloro-1-phenylpropan-1-one 2-CHLORO-1-PHENYLPROPAN-1-ONE 1-Propanone,2-chloro-1-phenyl- 1-(2-chlorophenyl)propan-1-one 1-(2-Chlorophenyl)-1-propanone benzene, 1-chloro-3,5-dimethoxy- (2R)-2-chloro-1-phenylpropan-1-one 1-Propanone, 2-chloro-1-phenyl- (9CI) |
CAS | 6084-17-9 |
EINECS | 230-330-2 |
InChI | InChI=1/C9H9ClO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,1H3/t7-/m1/s1 |
Molecular Formula | C9H9ClO |
Molar Mass | 168.62 |
Density | 1.560 g/cm3(Temp: 25 °C) |
Melting Point | 213-214 °C |
Boling Point | 80 °C(Press: 0.3 Torr) |
Flash Point | 118.4°C |
Vapor Presure | 0.0351mmHg at 25°C |
Storage Condition | Room Temprature |
Refractive Index | 1.5430-1.5470 |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
introduction | α-haloketone, as a kind of organic synthetic block with extremely high electrophilic activity, has been widely used in organic synthetic chemistry. At the same time, as an important structural unit, it also plays an extremely important role in pharmaceutical chemistry and pesticide chemistry. 2-Chlorophenylacetone is an important chemical raw material and pharmaceutical intermediate. |
preparation | step 1: preparation of enol silyl ether: adding phenylketone (1g,8 mmol) to a 50 mL two-mouth bottle, cooling the solution to 0 ℃ under the condition of nitrogen protection, and then adding 10 mL anhydrous THF solution, then add lithium diisopropylamide (2mol/L,4.2 mL) to it drop by drop. After dropping, remove the ice water mixture for cooling and stir for 1 h at room temperature. When the solution turns yellow, the reaction mixture is cooled to 0 ℃ again, trimethylchlorosilane (1.04g,9.6 mmol) is added dropwise to it, stirred at room temperature, and TLC is detected until the reaction is over. The solvent was removed by vacuum distillation, and the obtained oily liquid was separated by column chromatography (pure petroleum ether) to obtain product 1a (1.3g, yield: 84%). Step 2: Preparation of α-chlorophenylacetone: Iodobenzene diacetate (2a) (0.244g,0.75 mmol) is added to a 50 mL two-mouth bottle, and MeCN (5 mL) solution of phenylketenol silyl ether (1a) (0.096g,0.5 mmol) and trimethylchlorosilane (3a) (0.108g,1 mmol) is added to the system under the condition of nitrogen protection. The reaction system was stirred at room temperature and tested with TLC until the reaction was complete. After the solvent was removed by vacuum distillation, the residue was separated by column chromatography [V (petroleum ether) ∶V (ethyl acetate) = 10 ∶ 1]. Finally, the colorless liquid 4l(α-chlorophenylacetone) was isolated with 84% yield. |