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| | 2-Acetyl-4-chlorothiophene Basic information |
| Product Name: | 2-Acetyl-4-chlorothiophene | | Synonyms: | 1-(4-chlorothien-2-yl)ethanone;2-Acetyl-4-chlorothiophene, 98;4-chloro-2-acetothiophene;1-(4-chlorothiophen-2-yl)ethan-1-one;1-(4-Chlorothiophen-2-yl)ethanone;Ethanone, 1-(4-chloro-2-thienyl)-;2-acetyl-4-chlopothiophene;Avatrombopag Impurity 26 | | CAS: | 34730-20-6 | | MF: | C6H5ClOS | | MW: | 160.62 | | EINECS: | 677-855-7 | | Product Categories: | Intermediate;Sulfur compounds | | Mol File: | 34730-20-6.mol |  |
| | 2-Acetyl-4-chlorothiophene Chemical Properties |
| 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 |
| Risk Statements | 36 | | Safety Statements | 26 | | RIDADR | UN2810 | | HazardClass | 6.1 | | HS Code | 2934999090 |
| | 2-Acetyl-4-chlorothiophene Usage And Synthesis |
| 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. | | Uses | 2-Acetyl-4-chlorothiophene serves as a precursor in the synthesis of various arylated thiophene derivatives.[2] | | 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] Beydoun, K., & Doucet, H. (2011). Palladium-catalyzed direct 5-arylation of formyl- or acetyl-halothiophene derivatives. Journal of Organometallic Chemistry, 696(9), 1749–1759. https://doi.org/10.1016/j.jorganchem.2010.12.021
[2] Bensaid, S., & Doucet, H. (2012). Solvent‐Free Palladium‐Catalyzed Direct Arylation of Heteroaromatics with Aryl Bromides. ChemSusChem, 5(8), 1559–1567. https://doi.org/10.1002/cssc.201100771 |
| | 2-Acetyl-4-chlorothiophene Preparation Products And Raw materials |
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