| Identification | Back Directory | [Name]
1,3-BENZODIOXOLE-4-CARBOXYLIC ACID | [CAS]
5768-39-8 | [Synonyms]
BUTTPARK 27\02-57
o-Piperonylic acid
RARECHEM AL BE 0228
2,3-Methylene dioxy benzoic acid
1,3-BENZODIOXOLE-4-CARBOXYLIC ACID
Benzo[1,3]dioxole-4-carboxylic acid
benzo[d][1,3]dioxole-4-carboxylic acid
1,3-Benzodioxole-4-carboxylic acid 97+%
2,3-methylenedioxyphenylcarboxylic acid
4-Carboxy-1,3-benzodioxole, 2,3-(Methylenedioxy)benzoic acid
N'-[(E)-(5-bromo-3-indolylidene)methyl]-2-hydroxy-2-phenylacetohydrazide | [Molecular Formula]
C8H6O4 | [MDL Number]
MFCD01076411 | [MOL File]
5768-39-8.mol | [Molecular Weight]
166.13 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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