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| | 2-(Trichloroacetyl)pyrrole Basic information |
| | 2-(Trichloroacetyl)pyrrole Chemical Properties |
| Melting point | 72-74 °C (lit.) | | Boiling point | 285℃ | | density | 1.591 | | Fp | 126℃ | | storage temp. | 2-8°C | | solubility | Chloroform, Methanol | | form | Powder | | pka | 14.18±0.50(Predicted) | | color | Pale gray | | InChI | 1S/C6H4Cl3NO/c7-6(8,9)5(11)4-2-1-3-10-4/h1-3,10H | | InChIKey | BBFDGMDENAEMKF-UHFFFAOYSA-N | | SMILES | ClC(Cl)(Cl)C(=O)c1ccc[nH]1 | | CAS DataBase Reference | 35302-72-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38-36/37//38 | | Safety Statements | 26-36 | | RIDADR | UN 1759 8/PG III | | WGK Germany | 3 | | HazardClass | IRRITANT | | PackingGroup | III | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-(Trichloroacetyl)pyrrole Usage And Synthesis |
| Uses | 2-(Trichloroacetyl)pyrrole, is a building block used for the synthesis of more complex pharmaceutical compounds, such as Oroidin, Hymenidin and Clathrodin. | | General Description | 2-(Trichloroacetyl)pyrrole is a 2-substituted pyrrole. It undergoes acylation to afford 4-acyl derivatives (4-formyl to 4-hexanoyl). | | Synthesis | To a stirred solution of 2,2,2-trichloroacetyl chloride (25.5 mL, 0.227 mol) in anhydrous ether (45 mL) was added pyrrole (14.3 mL, 0.206 mol) slowly and dropwise at 0°C in an ice bath. The reaction mixture was stirred continuously. After the reaction was carried out for 2 days, brine solution (300 mL) was added to the reaction solution. Subsequently, the mixture was extracted with ethyl acetate (3 x 100 mL) and water (100 mL). The organic extracts were combined, dried with anhydrous magnesium sulfate (MgSO), and then evaporated to remove the solvent to afford the target product 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone as a brown solid (43.6 g, 99% yield). | | References | [1] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 897 - 905
[2] Journal of Organic Chemistry, 1993, vol. 58, # 25, p. 7245 - 7257
[3] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6698 - 6702
[4] Patent: EP3248968, 2017, A1. Location in patent: Paragraph 0097
[5] Organic Letters, 2011, vol. 13, # 17, p. 4550 - 4553 |
| | 2-(Trichloroacetyl)pyrrole Preparation Products And Raw materials |
| Raw materials | Pyrrole-->Trichloroacetyl chloride | | Preparation Products | 10Z-HYMENIALDISINE-->1H-Pyrrole-2-carboxylicacid,4-formyl-,methylester(9CI)-->1H-Pyrrole-2,5-dicarboxylic acid-->ethyl 4-formyl-1H-pyrrole-2-carboxylate-->Methyl 4-bromopyrrole-2-carboxylate-->1H-Pyrrole-2-carboxamide,N-ethyl-(9CI)-->2,2,2-Trichloro-1-[4-(2-methylbenzoyl)-1H-pyrrol-2-yl]-1-ethanone-->2,2,2-Trichloro-1-[4-(2-phenylacetyl)-1H-pyrrol-2-yl]-1-ethanone-->1H-Pyrrole-2-carboxamide, N-methoxy--->1H-Pyrrole-2-carboxylic acid 4-fluoro-benzylamide-->4,5-Dibromo-1H-pyrrole-2-carbohydrazide |
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