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| | 5-Formyl-2-thiophenecarboxylic acid Basic information |
| | 5-Formyl-2-thiophenecarboxylic acid Chemical Properties |
| Melting point | 169 °C | | Boiling point | 371.4±27.0 °C(Predicted) | | density | 1.514±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | powder to crystal | | pka | 3.05±0.10(Predicted) | | color | Light yellow to Brown | | InChI | InChI=1S/C6H4O3S/c7-3-4-1-2-5(10-4)6(8)9/h1-3H,(H,8,9) | | InChIKey | VFEAMMGYJFFXKV-UHFFFAOYSA-N | | SMILES | C1(C(O)=O)SC(C=O)=CC=1 | | CAS DataBase Reference | 4565-31-5(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38-36 | | Safety Statements | 26-36 | | Hazard Note | Irritant | | HS Code | 29349990 |
| | 5-Formyl-2-thiophenecarboxylic acid Usage And Synthesis |
| Chemical Properties | Bright red solid | | Uses | 5-Formyl-2-thiophenecarboxylic acid is a thiophene derivative as immunomodulating agents useful in the treatment of autoimmune diseases. | | Pharmaceutical Applications | 5-FORMYL-2-THIOPHENECARBOXYLIC ACID can be used in route for the Preparation of M3
antagonist-PDE4 inhibitor (MAPI) compounds with Carbamate Scaffold[2], MAPI compounds is used for the inhaled
treatment of pulmonary diseases. | | Synthesis | General procedure for the synthesis of 5-formyl-2-thiophenecarboxylic acid from methyl 5-formylthiophene-2-carboxylate: the compound methyl 5-formylthiophene-2-carboxylic acid (2 g, 12.8 mmol) was dissolved in 200 mL of a mixed solvent (THF:H2O = 1:1), and the hydrolysis reaction was carried out by adding KOH (1.1 g, 19.2 mmol). Upon completion of the reaction, THF was removed by distillation under reduced pressure.Subsequently, the pH of the aqueous layer was adjusted to 1-2 with 1N HCl solution and extracted with ethyl acetate (200 mL × 5), resulting in the target compound 5-formyl-2-thiophenecarboxylic acid (1.2 g, 59% yield).1H NMR (300 MHz, CDCl3) δ 10.00 (s, 1H), 7.93- 7.92 (d, J = 3.92 Hz, 1H), 7.78-7.77 (d, J = 3.9 Hz, 1H).13C NMR (300 MHz, CDCl3) δ 182.2, 163.30, 141.57, 139.70, 133.79, 132. | | References | [1] Patent: WO2004/37808, 2004, A1. Location in patent: Page 14-15; 93
[2] Armani, E. et.al. (2021). Discovery of M3 Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease. Journal of Medicinal Chemistry, 64 13, 9100–9119. https://doi.org/10.1021/acs.jmedchem.1c00204 |
| | 5-Formyl-2-thiophenecarboxylic acid Preparation Products And Raw materials |
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