| Identification | More | [Name]
5-Nitroisatin | [CAS]
611-09-6 | [Synonyms]
5-NITRO-1H-INDOLE-2,3-DIONE
5-NITROINDOLE-2,3-DIONE
5-NITROISATIN
AKOS B022561
AKOS BBS-00006405
LABOTEST-BB LT00146672
1H-Indole-2,3-dione,5-nitro-
5-nitro-1h-indole-3-dione
5-nitro-indole-3-dione
5-nitro-isati
Indole-2,3-dione, 5-nitro-
Isatin, 5-nitro-
2,3-dihydro-5-nitroindole-2,3-dione
Nitroisatin
5-Nitroisatin,98+%
5-Nitro-2,3-indolinedione
5-Nitroindoline-2,3-dione
5-Nitroisatin (5-Nitro-1H-indole-2,3-dione) | [EINECS(EC#)]
210-252-5 | [Molecular Formula]
C8H4N2O4 | [MDL Number]
MFCD00005720 | [Molecular Weight]
192.13 | [MOL File]
611-09-6.mol |
| Chemical Properties | Back Directory | [Appearance]
orange-yellow to orange crystalline powder | [Melting point ]
251 °C (dec.) (lit.) | [Boiling point ]
328.09°C (rough estimate) | [density ]
1.5513 (rough estimate) | [refractive index ]
1.4900 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
8.06±0.20(Predicted) | [color ]
Orange-yellow to orange | [BRN ]
180223 | [InChI]
InChI=1S/C8H4N2O4/c11-7-5-3-4(10(13)14)1-2-6(5)9-8(7)12/h1-3H,(H,9,11,12) | [InChIKey]
UNMYHYODJHKLOC-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C([N+]([O-])=O)C=C2)C(=O)C1=O | [CAS DataBase Reference]
611-09-6(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-indole-2,3-dione, 5-nitro-(611-09-6) |
| Questions And Answer | Back Directory | [Preparation]
Isatin 30 (14.7 g, 0.1 mol) was added to conc. H2SO4 (121 ml) cooled to 0 ºC in an ice-salt bath. Fuming HNO3 (4.2 ml) was added to this, drop by drop, in such a way that temperature should not rise above 5 ºC. The reaction mixture was allowed to stand for about 30 minutes and then poured over crushed ice (500 g). A yellow precipitate separated immediately. The 5-Nitroisatin was filtered and washed with water and air dried to a constant weight (15 g). Yield : 85% |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R68:Possible risk of irreversible effects.
R22:Harmful if swallowed. | [Safety Statements ]
S7:Keep container tightly closed .
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
NL7970000
| [HazardClass ]
IRRITANT | [HS Code ]
29337900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Carc. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
orange-yellow to orange crystalline powder | [Uses]
Reactant for preparation of:
- Potential antibacterial and antifungal agents
- spiro[indole-thiazolidinones] as a medicinally important scaffold
- Potential antimycobacterial agents
- Anticonvulsant agents
- Inhibitors of human transglutaminase 2
- Anthelmintic agents
- Anti-human immunodeficiency virus (HIV) agents
- Antimicrobial agents
- Potential antitubercular agents
- Inhibitors of acetylcholinesterase
| [Definition]
ChEBI: 5-Nitroisatin is a member of indoles. It has a role as an anticoronaviral agent. | [Synthesis]
The general procedure for the synthesis of 5-nitroindigo red from 5-nitroindole was as follows: a solution of anhydrous acetonitrile (4.0 mL) with 5-nitroindole (0.5 mmol), and iodobenzene diacetate (PIDA, 0.25 mmol) was added sequentially by the addition of a stirrer to a flask that had been pre-dried in an oven. To the reaction mixture, 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO, 0.5 mmol) was added under air atmosphere. The reaction mixture was stirred at room temperature until thin layer chromatography (TLC) analysis showed complete conversion of the feedstock. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 x 10 mL). The organic phases were combined and dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by silica gel column chromatography. | [References]
[1] Synthesis, 2007, # 5, p. 693 - 696
[2] Synlett, 2008, # 13, p. 2023 - 2027
[3] Synthetic Communications, 2012, vol. 42, # 23, p. 3419 - 3428
[4] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6385 - 6388 |
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