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| | 2-Amino-6-fluorobenzoic acid Basic information |
| | 2-Amino-6-fluorobenzoic acid Chemical Properties |
| Melting point | 167-169 °C (lit.) | | Boiling point | 223.67°C (rough estimate) | | density | 1.3021 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | soluble in Methanol | | pka | 4.01±0.10(Predicted) | | form | Crystalline Powder | | color | Yellow to brown | | BRN | 3540926 | | Major Application | peptide synthesis | | InChI | InChI=1S/C7H6FNO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,9H2,(H,10,11) | | InChIKey | RWSFZKWMVWPDGZ-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=C(F)C=CC=C1N | | CAS DataBase Reference | 434-76-4(CAS DataBase Reference) | | NIST Chemistry Reference | Anthralic acid, 6-fluoro-(434-76-4) |
| Hazard Codes | Xi | | 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-6-fluorobenzoic acid Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | Used in the synthesis of a novel benzamide with potent neuroleptic activity. 5- fluoro-2-methyl-3,l-benzoxazin-4-one was obtained from 2-amino-6-fluorobenzoic acid. The condensation of 2-amino-6-fluorobenzoic acid methyl ester and (4-fluorophenyl) acetyl chloride with N,N-dimethylamino-4-pyridine in CH 2 Cl 2 to give 2-fluoro-6-[2-(4-fluoro-phenyl)-acetylamino]-benzoic acid methyl ester in 61% yield. 2 Amino 6 fluorobenzoic acid is another easily ac cessible synthon for construction of monofluorinated heterocycles. Reactions of 2,3,4,6-tetra-O-acetyl-n-D_glucopyranosyl bromide (2) with p-hydroxybenzaldehyde, trifluoromethyl and fluoro substi- tuted aniline and 2-amino-6-fluorobenzoic acid gave lO-(Pformyl- pheny1)-2,3,4,6-tetra-O-acetyl-(3-D-glucopyranoside. 2-Fluoro-6-iodobenzoic acid,a loose white crystal,was synthesized by using 2-amino-6-fluorobenzoic acid as the starting material. | | Definition | ChEBI: 2-Amino-6-fluorobenzoic acid is an aminobenzoic acid. | | reaction suitability | reaction type: solution phase peptide synthesis | | Mechanism of action | 2-Amino-6-fluorobenzoic acid (6-FABA) has been identified as a novel anti-Mycobacterium tuberculosis agent (MIC = 5.0 μM). Its mechanism of action involves exerting antibacterial activity by interfering with the tryptophan (Trp) biosynthetic pathway in Mycobacterium tuberculosis. | | storage | Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents. | | Synthesis | The synthesis of 2-Amino-6-fluorobenzoic acid is as follows:
A 50 ml three-necked flask was charged with 1.85 g (10 mmol) of 6-fluoro-2-nitrobenzoic acid, 25.6 mg (0.2 mmol) of molybdenum dioxide, and 76.8 mg of activated carbon. 30 ml of absolute ethanol was added dropwise 1.25 g (20 mmol) of hydrazine hydrate (80%) at room temperature. After the reaction was completed at room temperature for 7 h, TLC monitoring showed that the reaction was completed, filtered, and the filtrate was concentrated, then ethyl acetate (20 mL) and water (10 ml) were added and extracted. The organic phase was washed with water and concentrated to give 1.5g desired product as a pale yellow solid, yield 96.8%, HPLC purity 99.6%.
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| | 2-Amino-6-fluorobenzoic acid Preparation Products And Raw materials |
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