2,3-Dihydro-1-benzofuran-2-carboxylic acid Chemical Properties

Melting point:

116-118

Boiling point:

340.5±31.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

3.17±0.20(Predicted)

color 

White to off-white

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-51-22

Safety Statements 

26-37/39

Hazard Note 

Irritant

HS Code 

29321900

2,3-Dihydro-1-benzofuran-2-carboxylic acid Usage And Synthesis

Chemical Properties

White solid

Uses

This compound is the starting material in the synthesis of (dihydro)benzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 495, 1987 DOI: 10.1002/jhet.5570240236

Synthesis

a) Synthesis of (R,S)-2,3-dihydro-benzofuran-2-carboxylic acid (54a): commercially available benzofuran-2-carboxylic acid (Aldrich Chemical Company, 27 g, 167.7 mmol) was dissolved in ethyl acetate (300 mL). The hydrogenation reaction was catalyzed by 10% Pd/C (20 g) at 65-70 psi hydrogen pressure for 2 days. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was evaporated. A solvent mixture of ethyl acetate-hexane (1:6) was added to the residue for recrystallization. Filtration afforded benzodihydrofuran-2-carboxylic acid as a crystalline solid (20.23 g, 74% yield). Melting point: 116-117 °C. 1H NMR (300 MHz, CDCl3) δ: 11.05 (brs, 1H), 7.17 (m, 2H), 6.91 (m, 2H), 5.24 (dd, 1H), 3.63 (dd, 1H), 3.42 (dd, 1H).

References

[1] Patent: US2005/54630, 2005, A1. Location in patent: Page/Page column 42
[2] Justus Liebigs Annalen der Chemie, 1883, vol. 216, p. 169
[3] Chemische Berichte, 1906, vol. 39, p. 496
[4] Farmaco, 1998, vol. 53, # 12, p. 764 - 772
[5] Patent: US2008/200540, 2008, A1. Location in patent: Page/Page column 18

2,3-Dihydro-1-benzofuran-2-carboxylic acid(1914-60-9)Related Product Information

• Tetrahydrofuran
• 2,5-Dihydrofuran
• Potassium hydrogen phthalate
• 2,3-Dihydrofuran
• 2,3-Dihydrobenzofuran
• Dibenzofuran
• Benzofuran
• Ascoric Acid
• 2-ETHOXYCARBONYL-3-COUMARANONE
• POLY(TETRAHYDROFURAN) STANDARD 15000
• 2,3-DIHYDRO-1-BENZOFURAN-5-CARBOXYLIC ACID
• 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBOXYLIC ACID
• 2,3-Dihydro-1-benzofuran-7-carboxylic acid
• Trimellitic Anhydride
• Benzofuran-2-carboxylic acid
• 1,2-DIHYDRONAPHTHO[2,1-B]FURAN-2-CARBOXYLIC ACID
• AA 193
• 5-METHOXY-2,3-DIHYDRO-BENZOFURAN-2-CARBOXYLIC ACID