3-(3-FURYL)ACRYLIC ACID Chemical Properties

Melting point:

155-158 °C(lit.)

Boiling point:

261.4±15.0 °C(Predicted)

Density 

1.280±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform, Methanol

form 

Solid

pka

4.20±0.10(Predicted)

color 

Pale Yellow

Water Solubility 

Sparingly soluble in water (0.56 g/L at 25°C).

BRN 

1306450

InChI

InChI=1S/C7H6O3/c8-7(9)2-1-6-3-4-10-5-6/h1-5H,(H,8,9)

InChIKey

JHAPZUDWRRBZHZ-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC1C=COC=1

CAS DataBase Reference

39244-10-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2932990090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-(3-FURYL)ACRYLIC ACID Usage And Synthesis

Uses

3-(3-Furyl)acrylic acid is used as an intermediate in chemical research and pharmaceuticals.

Synthesis

To 12 mL of pyridine, 10.0 g of 3-furaldehyde and 15.0 g of malonic acid were added and heated with stirring at 80°C to 90°C for 2 hours. Upon completion of the reaction, the reaction solution was poured into ice water and the pH was adjusted to weakly acidic with 1 N hydrochloric acid. The precipitated crystals were collected by filtration, dissolved in ethyl acetate and the organic phase was washed with 1 N hydrochloric acid. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized by ethyl acetate-hexane mixed solvent to give 11.78 g (82% yield) of 3-(3-furyl)acrylic acid. The product was characterized by 1H-NMR (CDCl3): δ 7.70-7.67 (m, 2H), 7.45 (s, 1H), 6.62-6.61 (m, 1H), 6.16 (d, J = 15.8 Hz, 1H). Mass spectral analysis showed m/e: 138 (M+, base peak).

References

[1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 24, p. 5483 - 5485
[2] ChemMedChem, 2018, vol. 13, # 18, p. 1972 - 1977
[3] Heterocycles, 1984, vol. 22, # 8, p. 1747 - 1757
[4] Patent: EP1724267, 2006, A1. Location in patent: Page/Page column 128
[5] Patent: WO2016/37578, 2016, A1. Location in patent: Page/Page column 111

3-(3-FURYL)ACRYLIC ACID(39244-10-5)Related Product Information

• 3-(3-FURYL)ACRYLIC ACID
• 3-(2-Furyl)acrylic acid
• trans-3-Furanacrylic acid
• 3-(3-Furyl)acrylic acid propyl ester
• (2E)-3-[5-(2,3-DICHLOROPHENYL)-2-FURYL]ACRYLIC ACID
• ABERCHROME 670
• (2E)-3-[5-(2-METHYL-4-NITROPHENYL)-2-FURYL]ACRYLIC ACID
• 3-[5-(2-CHLOROPHENYL)-2-FURYL]ACRYLIC ACID
• (2E)-3-[5-(2-METHYLCYCLOPROPYL)-2-FURYL]ACRYLIC ACID
• (2E)-3-[5-(3,4-DICHLOROPHENYL)-2-FURYL]ACRYLIC ACID
• 3-(2-Furyl)acrylic acid ethyl ester
• 3-(2-Furyl)acrylic acid methyl ester
• 3-[5-(2,4-DIFLUOROPHENYL)-2-FURYL]ACRYLIC ACID
• (2E)-3-[5-(2-BROMO-4-NITROPHENYL)-2-FURYL]ACRYLIC ACID
• (2E)-3-[5-[4-(AMINOCARBONYL)PHENYL]-2-FURYL]ACRYLIC ACID
• 4-[1-FURAN-3-YL-METH-(E)-YLIDENE]-ISOCHROMAN-1,3-DIONE
• RARECHEM AL BM 0196
• SALOR-INT L306789-1EA