1,3-BENZODIOXOLE-4-CARBOXYLIC ACID Chemical Properties

Melting point:

224 °C

Boiling point:

318.3±31.0 °C(Predicted)

Density 

1.468±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.97±0.20(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C8H6O4/c9-8(10)5-2-1-3-6-7(5)12-4-11-6/h1-3H,4H2,(H,9,10)

InChIKey

DBUAYOWCIUQXQW-UHFFFAOYSA-N

SMILES

O1C2=CC=CC(C(O)=O)=C2OC1

CAS DataBase Reference

5768-39-8

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Hazard Note 

Harmful

HS Code 

2932990090

1,3-BENZODIOXOLE-4-CARBOXYLIC ACID Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 3361, 1976 DOI: 10.1016/S0040-4039(00)93045-4

Synthesis

The general procedure for the synthesis of 1,3-benzodioxole-4-carboxylic acid from methyl benzo[d][1,3]meso-dioxole-4-carboxylate was as follows: methyl benzo[d][1,3]meso-dioxole-4-carboxylate (0.4 g, 2.22 mmol) was dissolved in methanol (8.0 mL), and 2.0 M aqueous KOH (2.2 mL) was added and stirred at room temperature. The reaction was stirred for 3 hours at room temperature. After completion of the reaction, the mixture was concentrated to about 3 mL, diluted with water (5 mL), and the pH was adjusted to ~3 with 2.0 M HCl. The precipitate was separated by filtration, washed sequentially with water and ether, and dried in vacuo to give 1,3-benzodioxole-4-carboxylic acid as a beige solid (0.38 g, 97% yield).1H NMR (400 MHz, DMSO-d6): δ = 7.28 (dd, J = 8.0, 1.2 Hz, 1H), 6.97 (dd, J = 8.0, 1.2 Hz, 1H), 6.89 (t, J = 8.0 Hz, 1H), 6.12 (s, 2H); 13C NMR (100 MHz, DMSO-d6): δ = 165.5, 148.9, 148.5, 122.9, 121.6, 113.8, 112.5, 102.1.

References

[1] Patent: WO2016/131098, 2016, A1. Location in patent: Page/Page column 167; 168; 169
[2] Steroids, 2010, vol. 75, # 12, p. 967 - 973
[3] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[4] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 604 - 614
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887

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