3-Fluoroanthranilic Acid CAS#: 825-22-9; ChemWhat Code: 1411322
Identification
| Product Name | 3-Fluoroanthranilic Acidine |
| IUPAC Name | 2-amino-3-fluorobenzoic acid |
| Molecular Structure |  |
| CAS Registry Number | 825-22-9 |
| EINECS Number | 630-115-7 |
| MDL Number | MFCD01569395 |
| Beilstein Registry Number | |
| Synonyms | 2-Amino-3-fluorobenzoic acid 825-22-9 3-Fluoroanthranilic Acid 2-amino-3-fluoro-benzoic acid 2-amino-3-fluorobenzenecarboxylic acid Benzoic acid, 2-amino-3-fluoro- 2-Azanyl-3-Fluoranyl-Benzoic Acid MFCD01569395 C7H6FNO2 4owm 3-fluoroanthranilate SCHEMBL161951 2-Amino-3-fluorobenzoic acid # DTXSID70342984 ACT00442 ACT00505 BCP24579 ZINC2574870 BBL100542 STL554336 AKOS005073124 AB09241 AC-3880 CS-W002787 KC-0713 SY005278 2-Amino-3-fluorobenzoic acid, AldrichCPR DB-024255 AM20060112 F0570 FT-0602026 EN300-56009 825A229 Q-103166 Q27453765 Z362758748 |
| Molecular Formula | C7H6FNO2 |
| Molecular Weight | 155.126 |
| InChI | InChI=1S/C7H6FNO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,9H2,(H,10,11) |
| InChI Key | C1=CC(=C(C(=C1)F)N)C(=O)O |
| Canonical SMILES | C1=CC(=CN=C1)N |
Physical Data
| Appearance | Off white to brown yellow crystalline powder |
| Melting Point, °C | Solvent (Melting Point) |
| 183 – 184 | CHCl3 |
| 171 | |
| 177 | |
| 183 | aq. ethanol |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | [(2)H6]acetone | 500.1 | |
| Chemical shifts | 13C | [(2)H6]acetone | 125.6 | |
| Spectrum | 1H | dimethylsulfoxide-d6 | ||
| Chemical shifts | 19F | dimethylsulfoxide-d6 | ||
| Chemical shifts | 19F | acetone-d6 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Temperature (IR Spectroscopy), °C |
| Bands | potassium bromide | 2-Amino-3-fluorobenzoic acid: [Benzoic acid, 2-amino-3-fluoro-] |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| aq. phosphate buffer | 308 |
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 3-Fluoroanthranilic Acid CAS-825-22-9
| Conditions | Yield |
| With N-Bromosuccinimide In dichloromethane at 0 – 20℃; for 1h; | 82% |
| With N-Bromosuccinimide In N,N-dimethyl-formamide at -10℃; for 1h; Inert atmosphere; | 80% |
| With N-Bromosuccinimide In dichloromethane at 20℃; for 3h; | 80% |
Experimental Procedure Step a. NBS (114.8 g, 645 mmol) was added in a portion wise manner over 1 h to a stirred orange/brown suspension of 2-amino-3-fluorobenzoic acid (100 g, 645 mmol) in DCM (1000 ml) at rt, and the resulting mixture was stirred at rt for 2 h. The mixture was then filtered and the resulting solid was washed sequentially with DCM (2 x 250 ml) and water (3 x 400 ml) before being dried under vacuum at 55°C for 7 h to give the desired product as a beige solid (121.4 g, 80%). LCMS (Method S): rt 2.93 min, m/z 232/234 [M-H]-; NMR (400 MHz, DMSO-d6) δ ppm 7.64 (m, 1H), 7.52 (dd, J= 10.9, 2.3 Hz, 1H) |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) ECHA C&L Notifications Summary Aggregated GH |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 155.129 |
| logP | 1.41 |
| HBA | 3 |
| HBD | 2 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 63.32 |
| Rotatable Bond (RotB) | 1 |
| Matching Veber Rules | 2 |
| Bioactivity |
| Quantitative Results |
| Quantitative Results | ||
| 1 of 14 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | 4-Hydroxy-3-quinoline-carboxylic acid derivatives | |
| 2 of 14 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | ADENOSINE A2A RECEPTOR ANTAGONISTS | |
| 3 of 14 | Comment (Pharmacological Data) | Bioactivities present |
| Measurement | Dissociation constant | |
| 4 of 10 | Assay Description | Hydrogen bond acidity of the compound was determined |
| Reference | Substituents effects on activity of kynureninase from Homo sapiens and Pseudomonas fluorescens |
| Use Pattern |
| 3-Fluoroanthranilic Acid CAS#: 825-22-9 is used as a pharmaceutical intermediate. |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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