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Isatin

CAS No.
91-56-5
Chemical Name:
Isatin
Synonyms
1H-Indole-2,3-dione;satin;Isatine;Isotin;lsatin;ISATIC ANHYDRIDE;2,3-INDOLINEDIONE;2,3-DIKETOINDOLINE;ISATIN;IsatinGr
CBNumber:
CB2447182
Molecular Formula:
C8H5NO2
Molecular Weight:
147.13
MDL Number:
MFCD00005718
MOL File:
91-56-5.mol
MSDS File:
SDS
Last updated:2023-09-07 18:57:57

Isatin 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
form Powder
pka 10.34±0.20(Predicted)
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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS02
Signal word  Warning
Hazard statements  H226
Precautionary statements  P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235
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

Isatin price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.20709 Isatin for synthesis 91-56-5 5G $37.3 2024-03-01 Buy
Sigma-Aldrich 114618 Isatin 97% 91-56-5 5g $35.3 2024-03-01 Buy
Sigma-Aldrich 8.20709 Isatin for synthesis 91-56-5 250G $121 2024-03-01 Buy
Sigma-Aldrich 114618 Isatin 97% 91-56-5 100g $37.7 2024-03-01 Buy
TCI Chemical I0080 Isatin >98.0%(GC)(T) 91-56-5 25g $39 2024-03-01 Buy
Product number Packaging Price Buy
8.20709 5G $37.3 Buy
114618 5g $35.3 Buy
8.20709 250G $121 Buy
114618 100g $37.7 Buy
I0080 25g $39 Buy

Isatin Chemical Properties,Uses,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.

59-48-3
91-56-5
Synthesis of Isatin from Oxindole
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View Lastest Price from Isatin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Isatin pictures 2024-03-19 Isatin
91-56-5
US $100.00 / kg 1kg 98.0min 10tons/month Asia Chem I and E (Jiangsu) Co Ltd
Isatin pictures 2024-03-19 Isatin
91-56-5
US $0.00 / Kg/Drum 1KG 99% 500mt/year Jinan Finer Chemical Co., Ltd
Isatin pictures 2023-08-26 Isatin
91-56-5
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
  • Isatin pictures
  • Isatin
    91-56-5
  • US $100.00 / kg
  • 98.0min
  • Asia Chem I and E (Jiangsu) Co Ltd
  • Isatin pictures
  • Isatin
    91-56-5
  • US $0.00 / Kg/Drum
  • 99%
  • Jinan Finer Chemical Co., Ltd
  • Isatin pictures
  • Isatin
    91-56-5
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
2,3-Diketoindoline Indole-2,3-dione 2,3-Indolinedione Isatin, 98% 100GR ISATIN / 2,3-INDOLINEDIONE IRSOGLADINEMALEATE ISATIN, PHARMACEUTICAL GRADE ISATIN, TECHNICAL GRADE Isatin, synthesis grade Isatin, reagent grade INDOLE-2,3-DIONE 98% Indole-2,3-dione(Isatin) Indolin-2,3-dion IsatinGr Isatin(Min98.5%) Isatin,98% NSC 9262 2,3-Indolinedione,94% 2,3-Indolinedione 〔Isatin〕 TIMTEC-BB SBB009100 O-AMINOPHENYLGLYOXALIC LACTIM O-AMINOBENZOYLFORMIC ACID O-AMINOBENZOYLFORMIC ANHYDRIDE AKOS BBS-00003223 2,3-DIHYDROINDOLE-2,3-DIONE 2,3-INDOLEDIONE 2,3-KETOINDOLINE Indoquinone Isatic acid lactam Isaticacidanhydride isaticacidlactam Isatinic acid anhydride isatinicacidanhydride Pseudoisatin ISATIN INDOLE-2,3-DIONE ,3-Dihydro-1H-indole-2,3-dione 2,3-Didetonindoline 2,3-Dioxo-2,3-dihydroindole 2,3-Dioxoindoline (E)-2-(3-oxobenzo[b]thiophen-2(3H)-ylidene)benzo[b]thiophen-3(2H)-one 1H-Indole-2,3-dione 98% ISATIN, 98%ISATIN, 98%ISATIN, 98%ISATIN, 98% Indoloquinone test solution(ChP) 3-Indolinedione Indoline-2 Isatin> Isatin,>98%,BS ISATIN FOR SYNTHESIS 250 G ISATIN FOR SYNTHESIS 5 G Flumazenil Impurity 16 Isatin (Indoline-2,3-dione) Indolequinone test solution Isatin, GR 99%+ Isatin extrapure AR, 99% Isatin 96% Indolo quinone indicator 2,3-DIKETOINDOLINE 2,3-INDOLINEDIONE Isatine