5,7-DIMETHYLISATIN Chemical Properties

Melting point:

245 °C

Boiling point:

306.47°C (rough estimate)

Density 

1.250

refractive index 

1.5060 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

10.43±0.20(Predicted)

Appearance

Yellow to orange Solid

Water Solubility 

Insoluble in water.

BRN 

143679

CAS DataBase Reference

39603-24-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25-22

RTECS 

NL7930000

HazardClass 

IRRITANT

HS Code 

29337900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

5,7-DIMETHYLISATIN Usage And Synthesis

Chemical Properties

red to red-brown powder

Uses

5,7-Dimethylisatin is used to produce cyano-(5,7-dimethyl-2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester by knoevenagel condensation with cyanoacetic acid ethyl ester. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Synthesis

The general procedure for the synthesis of 5,7-dimethylindoline-2,3-dione using (E)-N-(2,4-dimethylphenyl)-2-(hydroxyimino)acetamide as starting material was as follows: concentrated sulfuric acid (20 mL) was added to a 100 mL flask with vigorous stirring at 50°C, and N-2-(hydroxyimino)acetamide derivatives (7.0 g) were added in batches. The reaction temperature was maintained between 50°C and 75°C, followed by the addition of sulfide. After the addition was completed, the reaction mixture was warmed to 80°C and stirring was continued for 30 minutes. After completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice (250 g). The precipitated solid was collected and dried in air to give the crude product. The crude product was dissolved in 5% dilute sodium hydroxide solution (100 mL) and acidified with 4N hydrochloric acid (20 mL). The precipitated solid was filtered and dried thoroughly to give the purified target compound 5,7-dimethylindoline-2,3-dione.

References

[1] Journal of Chemical Research, Miniprint, 1998, # 7, p. 1425 - 1434
[2] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[4] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[5] Gazzetta Chimica Italiana, 1955, vol. 85, p. 840,841

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