| Identification | More | [Name]
5-IODOISATIN | [CAS]
20780-76-1 | [Synonyms]
5-IODO-2,3-INDOLINEDIONE
5-IODOINDOLE-2,3-DIONE
5-IODOINDOLINE-2,3-DIONE
5-IODOISATIN
1H-Indole-2,3-dione,5-iodo-
5-Iodo-1H-indole-2,3-dione
5-Iodo-2,3-dioxoin-doline
5-Iodoisatin 98%
5-Iodoisatine | [EINECS(EC#)]
244-035-1 | [Molecular Formula]
C8H4INO2 | [MDL Number]
MFCD00016899 | [Molecular Weight]
273.03 | [MOL File]
20780-76-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
276-280 °C(lit.) | [density ]
2.106±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
powder to crystal | [pka]
8.87±0.20(Predicted) | [color ]
Orange to Brown to Dark red | [Water Solubility ]
Soluble acetone, acetic acid, ethanol. Insoluble in water. | [Sensitive ]
Light Sensitive | [BRN ]
131248 | [CAS DataBase Reference]
20780-76-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
LIGHT SENSITIVE | [HS Code ]
29337900 |
| Hazard Information | Back Directory | [Uses]
5-Iodoisatin undergoes condensation reaction with phenol yields 5-iodophenolisatin, malonic acid yields 6-iodo-2-quinolone-4-carboxylic acid. | [Definition]
ChEBI:5-Iodoisatin is a member of indoles. It has a role as an anticoronaviral agent. | [General Description]
5-Iodoisatin undergoes condensation reaction with:
- phenol yields 5-iodophenolisatin
- malonic acid yields 6-iodo-2-quinolone-4-carboxylic acid
| [Synthesis]
1. Preheat concentrated sulfuric acid (275 mL) at 60 °C. After stopping the heating, add p-iodoacetoacetanilide (22.0 g, 75.9 mmol) in batches with stirring, controlling the temperature to no more than 65 °C.
2. The reaction mixture was heated at 80 °C for 15 min.
3. After cooling to room temperature, it was further cooled to 0 °C and then the reaction mixture was slowly poured into crushed ice (550 g) and stirred at 0 °C for 1 hour.
4. The orange colored precipitate formed was collected by filtration and washed with water (110 mL).
5. Dissolve the precipitate in preheated 10% aqueous sodium hydroxide solution (55 mL, 60 °C).
6. Acetic acid (16.5mL) was added and heated at 60°C for 30 minutes.
7. After cooling to room temperature, further cooled to 0 °C, the precipitate was collected by filtration, washed with water (11 mL) and dried under vacuum to give 5-iodoindigo (17.1 g, 62.7 mmol) as an orange solid.
8. Yield 83%; melting point 272-274 °C (literature value: 272-274 °C); IR (KBr) ν 1198, 1458, 1606, 1731-1751, 3241 cm-1; 1H NMR (200 MHz, DMSO-d6) δ 6.75 (d, 1H, J=8.2 Hz, H-7), 7.76 (d, 1H. J=1.8Hz, H-4), 7.88 (dd, 1H, J=1.8,8.2Hz, H-6), 11.11 (s, 1H, NH); 13C NMR (50MHz, DMSO-d6) δ 85.8 (C-5), 115.2 (C-7), 120.4 (C-3a), 132.9 (C-4), 142.0 (C 6), 150.7 (C-7a), 159.3 (C-2), 183.7 (C-3). | [References]
[1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838
[2] Tetrahedron, 2005, vol. 61, # 25, p. 6082 - 6087
[3] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[4] Chemische Berichte, 1924, vol. 57, p. 1773
[5] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206 |
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