4-CHLOROISATIN Chemical Properties

Melting point:

258 °C

Density 

1.519±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

9.44±0.20(Predicted)

color 

Light yellow to Brown

CAS DataBase Reference

6344-05-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

4-CHLOROISATIN Usage And Synthesis

Chemical Properties

Orange powder

Uses

4-Chloroisatin is an isatic acid derivative that performs a plant growth-regulating activity. Isatin compounds also performs selective inhibitory functions against carboxylesterases.

Synthesis

Chloral hydrate (8.93 g, 0.054 mol), anhydrous sodium sulfate (130 g, 0.40 mol), m-chloroaniline (0.05 mol), hydroxylammonium chloride (10.98 g, 0.158 mol), and concentrated hydrochloric acid (43 mL) were added to 120 mL of water in sequence. The resulting suspension was heated to 90 °C, maintained for 5 minutes and cooled to room temperature. The reaction mixture was filtered and washed with water (2 x 20 mL) to obtain the crude product. The crude product was added in batches to a 250 mL three-necked flask pre-filled with concentrated sulfuric acid (32.6 mL) and preheated to 65 °C, after which the mixture was heated to 80 °C and maintained for 20 minutes. After completion of the reaction, the solution was cooled to room temperature and slowly poured into 500 g of ice water with vigorous stirring for 4 hours. The intermediate 4-chloroindoline-2,3-dione was isolated by filtration, washed with water and recrystallized from ethanol in a final yield of 25.7% to 73.2%.

References

[1] Chinese Chemical Letters, 2013, vol. 24, # 10, p. 929 - 933

4-CHLOROISATIN(6344-05-4)Related Product Information

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