| Identification | Back Directory | [Name]
2-ACETYL-4-CHLOROTHIOPHENE | [CAS]
34730-20-6 | [Synonyms]
Avatrombopag Impurity 26
4-chloro-2-acetothiophene
2-ACETYL-4-CHLOROTHIOPHENE
2-acetyl-4-chlopothiophene
1-(4-chlorothien-2-yl)ethanone
2-Acetyl-4-chlorothiophene, 98
1-(4-Chlorothiophen-2-yl)ethanone
Ethanone, 1-(4-chloro-2-thienyl)-
1-(4-chlorothiophen-2-yl)ethan-1-one
2-ACETYL-4-CHLOROTHIOPHENE ISO 9001：2015 REACH | [EINECS(EC#)]
677-855-7 | [Molecular Formula]
C6H5ClOS | [MDL Number]
MFCD00082791 | [MOL File]
34730-20-6.mol | [Molecular Weight]
160.62 |
| Chemical Properties | Back Directory | [Boiling point ]
263.0±25.0 °C(Predicted) | [density ]
1.334 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [Appearance]
Light yellow to brown Liquid | [InChI]
InChI=1S/C6H5ClOS/c1-4(8)6-2-5(7)3-9-6/h2-3H,1H3 | [InChIKey]
FKESGQASARHBDC-UHFFFAOYSA-N | [SMILES]
C(=O)(C1SC=C(Cl)C=1)C |
| Hazard Information | Back Directory | [Description]
2-Acetyl-4-chlorothiophene is an oxychloride that belongs to the family of thiourea derivatives. It is synthesized by reacting phosphorus oxychloride with 2,3-dichloroacetophenone in a solvent such as dioxane or acetonitrile. The final product is purified by means of vacuum distillation and recrystallization from diethyl ether, hexane, and chlorinated hydrocarbons. | [Reactions]
Pd(OAc)2 catalysed the direct arylation of some functionalized halothiophene derivatives allowing the synthesis in only one step of polyfunctionalized arylated thiophenes. In the presence of 2-acetyl-4-chlorothiophene and various aryl bromides, the 5-arylation products were obtained in moderate to high yields employing only 0.5 mol% catalyst. Researchers studied the coupling of 2-acetyl-4-chlorothiophene with several aryl bromides employing 0.5 mol% Pd(OAc)2 as the catalyst and KOAc as the base. These phosphine-free catalyst reaction conditions allowed the successful coupling of several aryl bromides to more simple thiophene derivatives. Using such conditions, the 5-arylated thiophenes were obtained with high isolated yields. With this procedure, the priority for the arylation of this 2,4-disubstituted thiophene is the 5-position. Moreover, no formation of by-products, such as thiophene oligomers, due to the oxidative addition of this chlorothiophene to palladium was detected during these reactions[1].
| [Synthesis]
The general procedure for the synthesis of 2-acetyl-4-chlorothiophene from 2-acetylthiophene was as follows: 1-(2-thienyl)ethanone (5 g, 39.6 mmol) was dissolved in CHCl3 (50 mL) at 0 °C and AlCl3 (16 g, 0.119 mol) was added in batches. After 30 min of reaction, a solution of Cl2 in CCl4 (0.4 M) was added slowly and dropwise through the addition funnel. The reaction mixture was gradually warmed to 25 °C over 12 h and subsequently partitioned between ice water and dichloromethane. The organic layer was washed with 1N NaOH solution, dried over Na2SO4, concentrated and purified by column chromatography (silica gel, 0.5% EtOAc in hexane solution) to afford 2-acetyl-4-chlorothiophene (2.3 g, 36% yield) as a yellow oil.LC-MS (ES) m/z = 161 (M + H)+. | [References]
[1] Kassem Beydoun, Henri Doucet. “Palladium-catalyzed direct 5-arylation of formyl- or acetyl-halothiophene derivatives.” Journal of Organometallic Chemistry 696 9 (2011): Pages 1749-1759.
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