| Identification | More | [Name]
5-Fluoroisatin | [CAS]
443-69-6 | [Synonyms]
5-FLUORO-1H-INDOLE-2,3-DIONE
5-FLUOROINDOLE-2,3-DIONE
5-FLUOROINDOLINE-2,3-DIONE
5-FLUOROISATIN
5-FLUOROISATINE
AKOS BBS-00006537
BUTTPARK 24\07-36
5-Fluoroisatin,98%
5-Fluoroisatin 97%
5-FLUOROISATIN OR 5-FLUORO-1H-INDOLE-2,3-DIONE
5-Fluoroisatin97%
5-FLUOROISATIN 99+%
1H-Indole-2,3-dione, 5-fluoro-
5-FLUORO ISATINIC ANHYDRIDE
5-Fluoro-2,3-indoledione
NSC 39161 | [EINECS(EC#)]
628-890-1 | [Molecular Formula]
C8H4FNO2 | [MDL Number]
MFCD00022795 | [Molecular Weight]
165.12 | [MOL File]
443-69-6.mol |
| Chemical Properties | Back Directory | [Appearance]
red Crystalline Powder | [Melting point ]
224-227 °C (lit.) | [density ]
1.477±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, DMSO, Methanol | [form ]
Powder | [pka]
8.51±0.20(Predicted) | [color ]
Red | [Usage]
It showed antibacterial and antifungal activities.
| [BRN ]
131241 | [InChI]
InChI=1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12) | [InChIKey]
GKODDAXOSGGARJ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(F)C=C2)C(=O)C1=O | [CAS DataBase Reference]
443-69-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29337900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
red Crystalline Powder | [Uses]
It showed antibacterial and antifungal activities.
| [Definition]
ChEBI: 5-Fluoroisatin is a member of indoles. It has a role as an anticoronaviral agent. | [General Description]
5-Fluoroisatin has been reported as the precursor of the Sunitinib (Sutent) drug. 5-Fluoroisatin has been approved by the Food and Drugs Administration (FDA) in 2006 for the treatment of renal cell carcinoma (RCC) and gastrointestinal stromal tumor (GIST). | [Synthesis]
Concentrated sulfuric acid (24.0 mL) was added to a dry 150 mL three-necked flask and heated to 50 °C. The intermediate synthesized above (2a-2d, 30.0 mmol) was slowly added and the color of the solution gradually deepened to black as the intermediate was added. After the addition was completed, the reaction temperature was raised to 80 °C and the reaction was maintained for 20 min. Subsequently, crushed ice (100 g) was slowly added to the reaction system, at which time the ice-water mixture showed a reddish brown color. After standing, the reaction mixture was filtered and washed with deionized water until neutral. The resulting solid was dissolved in 10.0% NaOH solution (90 mL), the pH was adjusted to 4 with concentrated hydrochloric acid and filtered. The filtrate was continued to adjust the pH to 2 with concentrated hydrochloric acid, at which time a large amount of brick red solid precipitated. The solid was collected by filtration and dried to give the reddish brown target products 3a-3d. (Elution conditions: petroleum ether: ethyl acetate, v/v = 1:2, Rf = 0.4-0.6). | [References]
[1] Patent: CN107033064, 2017, A. Location in patent: Paragraph 0050; 0051; 0052; 0053
[2] Journal of the Brazilian Chemical Society, 2019, vol. 30, # 1, p. 198 - 209
[3] Synthetic Communications, 1999, vol. 29, # 20, p. 3627 - 3633
[4] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 12, p. 2919 - 2928 |
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