Chemical Properties
white to light yellow crystal powder
Uses
Used in the synthesis of styrylquinazolinones which are potential anticancer agents.
Uses
2-Amino-5-fluorobenzoic acid is used for the counterselection of TRP1, a commonly used genetic marker in the yeast Saccharoyces Cerevisiae. An antimetabolite for the tryptophan pathway in yeast, and is toxic by virtue of its antimetabolite conversion to 5-Fluorotryptophan. It can be used for the selection of tryptophan auxotroophs.
Definition
ChEBI: An aminobenzoic acid that is anthranilic acid in which the hydrogen at position 5 on the phenyl ring is replaced by fluorine.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
General procedure for the synthesis of 2-amino-5-fluorobenzoic acid from 2-nitro-5-fluorobenzoic acid: 2-nitro-5-fluorobenzoic acid (10 g, 54 mmol) was dissolved in ethanol (100 mL) and 10% Pd/C catalyst (0.5 g) was added. The reaction was stirred at room temperature for 4 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration. The filtrate was concentrated under reduced pressure to give 8.2 g (98% yield) of the white solid product 2-amino-5-fluorobenzoic acid. Product melting point: 142 °C. 1H NMR (DMSO-d6) δ: 6.71 (dd, J = 4.9, 8.9 Hz, 1H), 7.15 (dt, J = 2.9, 8.4 Hz, 1H), 7.37 (dd, J = 2.9, 9.8 Hz, 1H), 8.60 (s, 1H).EIMS m/z 156 (M + 1).
References
[1] Patent: WO2004/74218, 2004, A2. Location in patent: Page 106
[2] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 43
[3] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 44
[4] Patent: US5514676, 1996, A
[5] Journal of Biological Chemistry, 1954, vol. 207, p. 411,412
