| Identification | Back Directory | [Name]
4-Amino-3,5-difluorobenzoic acid | [CAS]
500577-99-1 | [Synonyms]
NSC 135302
4-Amino-3,5-difluorobenzoic acid
Benzoic acid, 4-amino-3,5-difluoro- | [Molecular Formula]
C7H5F2NO2 | [MDL Number]
MFCD03407440 | [MOL File]
500577-99-1.mol | [Molecular Weight]
173.12 |
| Chemical Properties | Back Directory | [Boiling point ]
294.2±40.0 °C(Predicted) | [density ]
1.536±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
powder | [pka]
4.18±0.10(Predicted) | [color ]
Faint to light orange |
| Hazard Information | Back Directory | [Uses]
4-Amino-3,5-difluorobenzoic Acid can be used to treat gastric cancer. | [Synthesis]
The general procedure for the synthesis of 3,5-difluoro-4-aminobenzoic acid from 4-amino-3,5-difluorobenzonitrile was as follows: 4-amino-3,5-difluorobenzonitrile (354.3 mg, 2.3 mmol) was suspended in a 1 M aqueous sodium hydroxide solution (12 mL), and the resulting suspension was heated and reacted for 16 hours at 110 °C. After completion of the reaction, the mixture was cooled to room temperature and washed with ether. Subsequently, the aqueous phase was acidified to pH=2 with 10% KHSO4/Na2SO4 buffer and extracted with ethyl acetate (2×). The ethyl acetate extracts were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3,5-difluoro-4-aminobenzoic acid (335 mg, 84% yield) as a yellow solid.1H NMR (300 MHz, chloroform-d) δ 7.66-7.58 (m, 2H). | [References]
[1] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5326 - 5333
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 250 - 255
[3] Patent: WO2018/136935, 2018, A1. Location in patent: Paragraph 00408
[4] Bioconjugate Chemistry, 2018, vol. 29, # 2, p. 324 - 334
[5] Journal of the American Chemical Society, 2012, vol. 134, # 51, p. 20597 - 20600 |
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