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| | 5-Chlorofuran-2-carboxylic acid Basic information |
| | 5-Chlorofuran-2-carboxylic acid Chemical Properties |
| Melting point | 179-180 °C | | Boiling point | 246.8±20.0 °C(Predicted) | | density | 1.515±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO, Methanol (Slightly) | | pka | 2.84±0.10(Predicted) | | form | solid | | color | Pale yellow | | InChI | 1S/C5H3ClO3/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8) | | InChIKey | NNTBDUTXMIMRKK-UHFFFAOYSA-N | | SMILES | OC(=O)c1ccc(Cl)o1 |
| RIDADR | 3261 | | WGK Germany | WGK 3 | | HazardClass | 8 | | PackingGroup | Ⅲ | | HS Code | 2932190090 | | Storage Class | 11 - Combustible Solids |
| | 5-Chlorofuran-2-carboxylic acid Usage And Synthesis |
| Chemical Properties | Type of white solid | | Uses | 5-Chlorofuran-2-carboxylic Acid is used as a reagent in the synthesis of 3-(5-Chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane, a a4b2 nicotinic acetylcholine receptor agonist used for treatment of cognitive disorders. | | Synthesis | Example 7: Synthesis of N-(5-chlorofuran-2-ylcarbonyl)-3,7-diazabicyclo[3.3.0]octane trifluoroacetate
Step 1: Preparation of 3,7-diazabicyclo[3.3.0]octane
A solution of silver nitrate (8.0 g, 47 mmol) in water (20 mL) was added to 80 mL of 10% aqueous sodium hydroxide and stirred to form a suspension. A 30% aqueous ammonium hydroxide solution was added slowly until the suspension became clear.
Step 2: Coupling reaction
To the above clarified solution was added a methanol (5mL) solution of 5-chlorofuran-2-carbaldehyde (3.0g, 23mmol, Aldrich Chemical) and stirred for 30 minutes at room temperature.
Step 3: Post-treatment
The reaction mixture was filtered and the filtrate was washed with ether (100 mL). Subsequently, the aqueous filtrate was adjusted with cold 20% sulfuric acid to a pH of about 3. The acidic aqueous phase was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, washed with saturated aqueous sodium chloride (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 3.2 g (95% yield) of a white solid product with a melting point of 178-179 °C. The product was extracted with ethyl acetate (3 x 100 mL).
Remarks: The synthesis method is easy to scale up and has been successfully carried out in several experiments with scale over 10g. | | References | [1] Patent: WO2008/57938, 2008, A1. Location in patent: Page/Page column 32
[2] Patent: WO2008/67644, 2008, A1. Location in patent: Page/Page column 36 |
| | 5-Chlorofuran-2-carboxylic acid Preparation Products And Raw materials |
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