Isatin Chemical Properties

Melting point:

193-195 °C (dec.) (lit.)

Boiling point:

267.22°C (rough estimate)

Density 

1.3067 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

1.4700 (estimate)

Flash point:

220 °C

storage temp. 

Store below +30°C.

solubility 

soluble

pka

10.34±0.20(Predicted)

form 

Powder

color 

Orange

PH

7 (1.9g/l, H2O, 20℃)

Water Solubility 

Soluble in water (1.9 g/L at 20°C).

Decomposition 

194 ºC

Merck 

14,5104

BRN 

383659

Stability:

Stable. Incompatible with strong acids.

InChIKey

JXDYKVIHCLTXOP-UHFFFAOYSA-N

LogP

0.45

CAS DataBase Reference

91-56-5(CAS DataBase Reference)

NIST Chemistry Reference

Isatin(91-56-5)

EPA Substance Registry System

1H-Indole-2,3-dione (91-56-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-24/25

RIDADR 

2811

WGK Germany 

1

RTECS 

NL7873000

Autoignition Temperature

220 °C

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29337900

MSDS

• Language:English Provider:1H-Indole-2,3-dione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Isatin Usage And Synthesis

Isatin

Isatin, is also known as indenedione, indole quinone. Its chemical name is indol(o)-2,3-dione,it is orange-red monoclinic prism crystal at room temperature. Bitter. The molecular weight is147.13. Melting point 203.5 ℃ (Part sublimation). Dissolved in water, hot ethanol, benzene, acetone, ether-soluble. Soluble in boiling alcohol, soluble in ether and boiling water  and it is reddish brown , soluble in caustic and solution is purple, it changes to yellow after placement. Its alcohol solution   has a very unpleasant odor. Weakly alkaline, it can salify with a perchlorate.
Above information of is edited by Andy from ChemicalBook (2016-11-19).

Chemical Properties

Orange-red monoclinic prism crystals. Melting point 203.5 ℃ (Part sublimation). Soluble in hot ethanol, ethyl ether-soluble, soluble in hot water, benzene, acetone, dissolved in alkali metal hydroxide oxide. The solution is purple, it turns yellow after placement, alkaline activity is extremely weak. Bitter.

Uses

(1) The product is used as medicine and dye intermediates ,and it is used for the production of drug  quinophan, dye disperse Yellow E-3G ; in chemical analysis,it is used as reagents for the determination of copper ions, mercaptans, thiophene,  indoxyl-beta-glucoside.
(2) Isatin as a reference material for the preparation of indigo and Maya blue; for the preparation of phthalazinone derivatives, spirooxindole derivatives, the expression of P-glycoprotein for multi-drug resistant cells; The ketone is fused to form indole-2-one as a tubercular mycobacterial protein tyrosine phosphatase B, a potent selective inhibitor, as a powerful antimicrobial and antifungal triazole-isatine complex, And the Knoevenagel enrichment reaction; the isatin is activated by the direct sp2/sp3C-H bond, and undergoes a reaction with the cyclopentadienyl-Pd (II) catalyzes the CH addition reaction to form 3-substituted-3-hydroxy 2-oxindole.

production method

Condensation of chloral and aniline  can generate  oximide-acetanilide, and then by cyclization, hydrolysis , isatin is obtained.

Chemical Properties

orange-red powder or crystals

Uses

Isatin is an endogenous monoamine oxidize (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes. Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles. It is used as chromatographic spray reagent for amino acid detection.

Uses

Isatin can be used as a reactant to prepare:

• Phthalazinone derivatives.
• Spirooxindole derivatives.
• Agents against multidrug-resistant cells expressing P-glycoprotein.
• Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.
• Triazole-isatine compounds as potential antibacterial and antifungal agents.
• Biologically relevant scaffolds such as spiro[indole-thiazolidinones].

It can be a reactant for:

• Cascade reactions with heterocyclic ketene aminals.
• Knoevenagel condensation reactions.

Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.

Uses

manufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.

Definition

ChEBI: An indoledione that is the 2,3-diketo derivative of indole.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 197, 1990 DOI: 10.1021/jo00288a033

Flammability and Explosibility

Non flammable

Biological Activity

isatin is a monoamine oxidase inhibitor.monoamine oxidase inhibitors have been used as therapies for the treatment of depression, particularly in treating atypical depression. monoamine oxidase inhibitors are also used in the treatment of parkinson's disease and other disorders.

in vitro

previous study found that isatin treatment at 1-400 μm for 24h could induce a significant dose-dependent increase in mtt metabolism by sh-sy5y cells, which was not due to the increase in cell division. in addition, isatin at the higher concentrations was able to trigger cell death, though mtt metabolism was still increased, indicating that the surviving cells were hypermetabolic. with a longer treatment, isatin was found to cause cell death in a dose-dependent manner, and the predominant mode of cell death was apoptosis at lower concentrations, while at the highest concentration increasing numbers of necrotic cells were also observed [1].

in vivo

animal study showed that the motor activity of japanese encephalitis virus (jev)-induced rats receiving isatin was improved significantly when compared with that of untreated jev-infected rats. in addition, isatin was able to prevent the decrease in striatal da levels in jev-rats and the increased turnover of dopamine (da) (dopac/da) induced by jev was significantly inhibited by isatin. such results indicated that the exogenously administered isatin was able to improve jev-induced parkinsonism via increasing the striatum da concentrations [2].

IC 50

15 μm

Purification Methods

Crystallise isatin from amyl alcohol and sublime it at 180o/1mm. In aqueous NaOH the ring opens to yield sodium o-aminobenzoylformate. [Beilstein 21 II 327, 567, 21 III/IV 4981, 21/10 V 221.]

References

[1] igosheva n,lorz c,o'conner e,glover v,mehmet h. isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. neurochem int.2005 aug;47(3):216-24.
[2] hamaue n,minami m,terado m,hirafuji m,endo t,machida m,hiroshige t,ogata a,tashiro k,saito h,parvez sh. comparative study of the effects of isatin, an endogenous mao-inhibitor, and selegiline on bradykinesia and dopamine levels in a rat model of parkinson's disease induced by the japanese encephalitis virus. neurotoxicology.2004 jan;25(1-2):205-13.

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