5-Nitroisatin Chemical Properties

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)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-40-68-22

Safety Statements 

7-22-36/37/39-45-36/37

RIDADR 

2811

WGK Germany 

3

RTECS 

NL7970000

HazardClass 

IRRITANT

HS Code 

29337900

MSDS

• Language:English Provider:5-Nitroisatin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Nitroisatin Usage And Synthesis

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%

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

5-Nitroisatin(611-09-6)Related Product Information

• Oxindole
• Isatoic Anhydride
• 1,3-DINITRONAPHTHALENE
• 4-Nitroacetophenone
• 4-Nitrobenzoic acid
• 3-Nitroacetophenone
• Indirubin
• Indole
• 4-Nitrofluorescein
• 1-(2,6-Dichlorophenyl)-2-hydroindole
• Nitromethane
• NITROGEN DIOXIDE
• 2,4,6-Trinitrotoluene
• 2,4-Dinitrophenylhydrazine
• Nitrobenzene
• 1,3-Dinitrobenzene
• 2,5-DINITROPHENOL
• 5-Nitroindole