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Cas Database

Name	Isatin	EINECS	202-077-8
CAS No.	91-56-5	Density	1.367 g/cm³
PSA	46.17000	LogP	0.95940
Solubility	Soluble in water (1.9 g/L at 20°C).	Melting Point	193-195 °C (dec.)(lit.)
Formula	C₈H₅NO₂	Boiling Point	360.3 °C at 760 mmHg
Molecular Weight	147.133	Flash Point	171.7 °C
Transport Information	N/A	Appearance	yellow to reddish crystalline solid
Safety	26-36-24/25	Risk Codes	36/37/38-20/21/22
Molecular Structure		Hazard Symbols	Xi,Xn
Synonyms	Indole-2,3-dione(8CI);2,3-Dihydro-1H-indole-2,3-dione;2,3-Dihydroindole-2,3-dione;2,3-Diketoindoline;2,3-Dioxo-2,3-dihydroindole;2,3-Dioxoindoline;2,3-Indolindione;2,3-Indolinedione;Isatic acid lactam;Isatin;Isatine;Isatinic acid anhydride;NSC 9262;Pseudoisatin;o-Aminobenzoylformic anhydride;	Article Data	309

Isatin Synthetic route

: 42366-35-8, 1769-41-1
hydroxyimino-N-phenylacetamide

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With sulfuric acid at 20 - 30℃; for 1.66667h; Temperature;	99%
With sulfuric acid at 70℃; for 0.00277778h; Microwave irradiation;	85%
With sulfuric acid at 65 - 90℃; for 0.5h;	81.3%

: 2-(2-aminophenyl)-N-hexyl-2-oxoacetamide

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h;	99%

: 64784-13-0, 482-89-3, 141901-19-1
indigo

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With ozone In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 70℃; for 24h; Solvent; Temperature; Large scale;	98.2%
With potassium dichromate; sulfuric acid In water at 43℃; for 1.5h; Cooling;	90%
With potassium dichromate; sulfuric acid In water at 43℃; for 1.5h;	90%
With potassium dichromate; sulfuric acid In water at 43℃; for 1.5h; Cooling;	90%
With potassium dichromate; sulfuric acid In water

: 92635-28-4
3,3-dibromo-1-methoxy-2-oxindole

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With methanol Heating;	98%

: 1477-50-5
Indole-2-carboxylic acid

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 48h; Inert atmosphere; Irradiation;	98%

: 59-48-3
2-oxoindole

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With oxygen; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 0.5h;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 2h; Reagent/catalyst; Solvent;	94%
With tert.-butylhydroperoxide In decane; acetonitrile at 80℃; for 0.285h; Catalytic behavior; Flow reactor; Green chemistry;	90%

: 113783-27-0
1-(2-iodoethynyl)-2-nitrobenzene

A: 2-iodo-3-oxo-3H-indole 1-oxide

B: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran for 16h; Inert atmosphere; Reflux;	A 89% B 8%

: 3-(tert-butylperoxy)-3-(4-methylbenzyl)indolin-2-one

A: 91-56-5
indole-2,3-dione

B: 104-87-0
4-methyl-benzaldehyde

Conditions

Conditions	Yield
With iron(III) chloride hexahydrate In acetonitrile at 100℃; Sealed tube;	A 88% B 89%

: 26340-47-6
3-Iodo-1H-indole

: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 35℃; for 6h;	89%

: 14204-24-1
N-(phenylthio)succinimide

: 3-((4-chlorophenyl)thio)indolin-2-one

A: C20H14ClNOS2

B: C20H14ClNOS2

C: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With dihydroquinine In dichloromethane at -70℃; for 12h; Reagent/catalyst; enantioselective reaction;	A n/a B 88% C 7%
With C29H44N3O3P In tetrahydrofuran at -70℃; for 84h; Reagent/catalyst; enantioselective reaction;	A n/a B 20% C 71%

Isatin Chemical Properties

IUPAC: 1H-indole-2,3-dione
CAS:91-56-5
The Molecular formula of INDOLE-2,3-DIONE(91-56-5):C₈H₅NO₂
The Molecular Weight of INDOLE-2,3-DIONE(91-56-5):147.13
Synonyms:Isatin;TIMTEC-BB SBB009100;O-AMINOPHENYLGLYOXALIC LACTIM;O-AMINOBENZOYLFORMIC ACID;O-AMINOBENZOYLFORMIC ANHYDRIDE;AKOS BBS-00003223;2,3-DIKETOINDOLINE;2,3-DIHYDROINDOLE-2,3-DIONE;2,3-INDOLEDIONE
EINECS:202-077-8
Density:1.367g/cm³
Melting Point:198-204^oC (Decomposes)(lit.)
Boiling Point:360.3^oC at 760 mmHg
Flash Point:220^oC
Solubility:Slightly soluble SOLVENT AUTOIGNITION
Appearance:yellow to reddish crystalline solid
liansport Information:25kgs
Product Categories:Intermediates;Heterocyclic Compounds;Indoles;Simple Indoles
Mol File:91-56-5.mol
storage temp.:Store at RT.
Decomposition:194^oC
Merck:14,5104
BRN:383659

Isatin History

INDOLE-2,3-DIONE(91-56-5) is an indole derivative. In 1841, Erdman and Laurent first obtained the compound as a product from the oxidation of indigo dye by nitric acid and chromic acids. The compound is found in many plants.Schiff bases of INDOLE-2,3-DIONE are investigated for their pharmaceutical properties.It was observed that it forms a blue dye if it is mixed with sulfuric acid and crude benzene. The formation of the blue indophenin was long believed to be a reaction with benzene. Victor Meyer was able to isolate the substance responsible for this reaction from benzene. This new heterocyclic compound was thiophene.

Isatin Uses

Indole-2,3-dione(91-56-5) is an endogenous monoamine oxidase inhibitor that is involved in stress and anxiety. It is an inhibitor of alkaline phosphatase, nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes.

Isatin Production

INDOLE-2,3-DIONE(91-56-5) can be produced by cyclicizing the condensation product of chloral hydrate, aniline and hydroxylamine in sulfuric acid.

Isatin Toxicity Data With Reference

1.	orl-rat LDLo:5 g/kg	IJPPAZ Indian Journal of Physiology and Pharmacology. 6 (1962),145.
2.	orl-mus LD50:300 mg/kg	NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. 55 (1959),1514.
3.	ipr-mus LD50:563 mg/kg	PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 15 (1981),858.

Isatin Consensus Reports

Reported in EPA TSCA Inventory.

Isatin Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x. See also ANHYDRIDES.

Safty informations about INDOLE-2,3-DIONE(91-56-5):
Hazard Codes:Xi,Xn
Risk Statements:36/37/38-20/21/22
36/37/38 (Irritating to the eyes ,piratory system and skin)
20/21/22(Harmful by inhalation, in contact with skin and if swallowed)
Safety Statements:26-36-24/25
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
36 (Wear suitable protective clothing)
24/25(Avoid contact with skin and eyes)
WGK Germany:1
RIDADR:2811
RTECS:NL7873000
HazardClass:6.1(b)
PackingGroup:III
HS Code:29337900

Isatin Specification

Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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