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)

form 

solid

pka

2.84±0.10(Predicted)

color 

Pale yellow

Safety Information

RIDADR 

3261

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2932190090

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(618-30-4)Related Product Information

• Mometasone furoate
• 2-Furoic acid
• 2-Tetrahydrofuroic acid
• (S)-(-)-Tetrahydro-2-furoic acid
• 3-Chloroperoxybenzoic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Allyl chloroformate
• (+)-MENTHYL CHLOROFORMATE
• Benzyl chloroformate
• t-butyl chloroformate
• Methyl chloroformate
• 5-CHLORO-2-FURALDEHYDE
• Ethyl chloroformate
• Difluorochloromethane
• 5-(Chlorosulfonyl)-2-furancarboxylic acid
• ETHYL 5-(CHLOROSULFONYL)-3-FUROATE
• 5-Chlorofuran-2-carboxylic acid
• 3-chloro-2-furoic acid