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Isatin

Isatin Chemical Properties Uses production method

Isatin

CAS No.91-56-5
Chemical Name:Isatin
CBNumber:CB2447182
Molecular Formula:C8H5NO2
Formula Weight:147.13
MOL File:91-56-5.mol

Isatin Property

Melting point 193-195 °C (dec.) (lit.)
Boiling point 267.22°C (rough estimate)
Density 1.3067 (rough estimate)
bulk density 600kg/m3
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)
EWG's Food Scores 1-3
FDA UNII 82X95S7M06
NIST Chemistry Reference Isatin(91-56-5)
EPA Substance Registry System 1H-Indole-2,3-dione (91-56-5)
UNSPSC Code 12352115
NACRES NA.22

Safety

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

NFPA 704:

	0
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H226
Precautionary statements P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235

Isatin Price More Price(19)

Brand: Sigma-Aldrich(India)
Product number: 114618
Product name : Isatin
Purity: 97%
Packaging: 5G
Price: ₹2460
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 114618
Product name : Isatin
Purity: 97%
Packaging: 100G
Price: ₹2950
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 114618
Product name : Isatin
Purity: 97%
Packaging: 500G
Price: ₹9807.45
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: I0080
Product name : Isatin
Purity: min. 98.0 %
Packaging: 25G
Price: ₹2300
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: I0080
Product name : Isatin
Purity: min. 98.0 %
Packaging: 100G
Price: ₹5200
Updated: 2022/05/26
Buy: Buy

Isatin Chemical Properties,Usage,Production

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 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 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 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.