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| | 2-Amino-5-fluorobenzoic acid Basic information |
| | 2-Amino-5-fluorobenzoic acid Chemical Properties |
| Melting point | 181-183 °C(lit.) | | Boiling point | 223.67°C (rough estimate) | | density | 1.3021 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 1.86±0.10(Predicted) | | form | Fine Crystalline Powder | | color | Light yellow to light brown | | BRN | 2803664 | | Major Application | peptide synthesis | | InChI | InChI=1S/C7H6FNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11) | | InChIKey | FPQMGQZTBWIHDN-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC(F)=CC=C1N | | CAS DataBase Reference | 446-08-2(CAS DataBase Reference) |
| Hazard Codes | Xi,T | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29224999 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-Amino-5-fluorobenzoic acid Usage And Synthesis |
| 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 |
| | 2-Amino-5-fluorobenzoic acid Preparation Products And Raw materials |
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