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Isatin
Cas No: 91-56-5
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High purity 91-56-5 Isatin
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Isatin
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91-56-5 1H-Indole-2,3-dione
Cas No: 91-56-5
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Amadis Chemical offer CAS#91-56-5;CAT#A843979
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Isatin
Cas No: 91-56-5
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91-56-5 Usage

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.]

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.

Definition

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

production method

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

Uses

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

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.

Chemical Properties

orange-red powder or crystals

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).
InChI:InChI:1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

91-56-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (114618)  Isatin   91-56-5 114618-500G 1,334.97CNY Detail
Aldrich (114618)  Isatin   91-56-5 114618-100G 402.48CNY Detail
Aldrich (114618)  Isatin   91-56-5 114618-5G 313.56CNY Detail
Sigma-Aldrich (58240)  Isatin  for spectrophotometric det. of proline and thiophene, ≥99.0% 91-56-5 58240-100G 397.80CNY Detail
Sigma-Aldrich (58240)  Isatin  for spectrophotometric det. of proline and thiophene, ≥99.0% 91-56-5 58240-25G 379.08CNY Detail
Alfa Aesar (A12468)  Isatin, 98%    91-56-5 2500g 2509.0CNY Detail
Alfa Aesar (A12468)  Isatin, 98%    91-56-5 500g 629.0CNY Detail
Alfa Aesar (A12468)  Isatin, 98%    91-56-5 100g 189.0CNY Detail
TCI America (I0080)  Isatin  >98.0%(GC)(T) 91-56-5 500g 1,610.00CNY Detail
TCI America (I0080)  Isatin  >98.0%(GC)(T) 91-56-5 100g 490.00CNY Detail
TCI America (I0080)  Isatin  >98.0%(GC)(T) 91-56-5 25g 205.00CNY Detail

91-56-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name isatin

1.2 Other means of identification

Product number -
Other names 2-methopropan-1-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:91-56-5 SDS

91-56-5Synthetic route

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

hydroxyimino-N-phenylacetamide

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

indole-2,3-dione

Conditions
ConditionsYield
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

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

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

indole-2,3-dione

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h;99%
Conditions
ConditionsYield
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
3,3-dibromo-1-methoxy-2-oxindole
92635-28-4

3,3-dibromo-1-methoxy-2-oxindole

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

indole-2,3-dione

Conditions
ConditionsYield
With methanol Heating;98%
Indole-2-carboxylic acid
1477-50-5

Indole-2-carboxylic acid

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

indole-2,3-dione

Conditions
ConditionsYield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 48h; Inert atmosphere; Irradiation;98%
2-oxoindole
59-48-3

2-oxoindole

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

indole-2,3-dione

Conditions
ConditionsYield
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%
1-(2-iodoethynyl)-2-nitrobenzene
113783-27-0

1-(2-iodoethynyl)-2-nitrobenzene

A

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

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

B

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

indole-2,3-dione

Conditions
ConditionsYield
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

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

A

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

indole-2,3-dione

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In acetonitrile at 100℃; Sealed tube;A 88%
B 89%
3-Iodo-1H-indole
26340-47-6

3-Iodo-1H-indole

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

indole-2,3-dione

Conditions
ConditionsYield
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 35℃; for 6h;89%
N-(phenylthio)succinimide
14204-24-1

N-(phenylthio)succinimide

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

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

A

C20H14ClNOS2

C20H14ClNOS2

B

C20H14ClNOS2

C20H14ClNOS2

C

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

indole-2,3-dione

Conditions
ConditionsYield
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%
3-(tert-butylperoxy)-3-(4-methoxybenzyl)indolin-2-one

3-(tert-butylperoxy)-3-(4-methoxybenzyl)indolin-2-one

A

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

indole-2,3-dione

B

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In acetonitrile at 100℃; Sealed tube;A 88%
B 82%
dioxindol
61-71-2

dioxindol

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

indole-2,3-dione

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper diacetate In 1,4-dioxane at 120℃; Schlenk technique;87%
With ammonium nitrate; acetic acid
3-thiocyanatoindole
23706-25-4

3-thiocyanatoindole

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

indole-2,3-dione

Conditions
ConditionsYield
With cerium(III) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 80℃; for 2.5h;87%
1-(Chloroacetyl)-1H-indole-2,3-dione
7218-25-9

1-(Chloroacetyl)-1H-indole-2,3-dione

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

indole-2,3-dione

Conditions
ConditionsYield
With thiourea In ethanol at 20 - 78℃;87%
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

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

indole-2,3-dione

Conditions
ConditionsYield
With cerium(III) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 80℃; for 3h;85%
With Oxone; sodium chloride In water; acetonitrile at 50℃; for 2h; Green chemistry;84%
With indium(III) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 80℃; for 2.5h;79%
With pyridinium chlorochromate In 1,2-dichloro-ethane at 80℃; for 4h;75%
1-indoline
496-15-1

1-indoline

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

indole-2,3-dione

Conditions
ConditionsYield
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry;84%
With iodine pentoxide In dimethyl sulfoxide at 80℃; Temperature; Reagent/catalyst;76%
With tert.-butylhydroperoxide; iodine In dimethyl sulfoxide at 80℃; for 24h;30%
3-diazo-1,2,3,4-tetrahydro-2,4-dioxo-quinoline
7270-61-3

3-diazo-1,2,3,4-tetrahydro-2,4-dioxo-quinoline

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

indole-2,3-dione

Conditions
ConditionsYield
With copper(I) bromide In water; benzonitrile at 140℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;84%
1-(2-iodoethynyl)-2-nitrobenzene
113783-27-0

1-(2-iodoethynyl)-2-nitrobenzene

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

indole-2,3-dione

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In acetone at 60℃; for 4h; Inert atmosphere;83%
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran for 16h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;60%
N-acetylindole
576-15-8

N-acetylindole

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

indole-2,3-dione

Conditions
ConditionsYield
With pyridinium chlorochromate In 1,2-dichloro-ethane at 80℃; for 3h;82%
N-phenylglycine ethyl ester
2216-92-4

N-phenylglycine ethyl ester

aniline
62-53-3

aniline

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

indole-2,3-dione

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol at 70℃; for 10h;81.6%
3-(2-aminophenyl)-2-(dimethyl-1-sulfonylidene)-3-oxopropanenitrile

3-(2-aminophenyl)-2-(dimethyl-1-sulfonylidene)-3-oxopropanenitrile

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

indole-2,3-dione

Conditions
ConditionsYield
With Oxone In tetrahydrofuran; water at 20℃; for 0.166667h; Solvent; Inert atmosphere;81%
indole-2,3-dione
91-56-5

indole-2,3-dione

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

isatine 3-benzoylhydrazone
55711-62-1

isatine 3-benzoylhydrazone

Conditions
ConditionsYield
at 20℃; for 3h; Solid phase reaction; condensation;100%
In methanol for 0.5h; Heating;75%
With ethanol
In ethanol
indole-2,3-dione
91-56-5

indole-2,3-dione

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

indophenazine
243-59-4

indophenazine

Conditions
ConditionsYield
In 1,4-dioxane for 0.25h; Heating;100%
In acetic acid for 0.1h; Microwave irradiation;97%
With acetic acid Sealed tube; Microwave irradiation;95%
indole-2,3-dione
91-56-5

indole-2,3-dione

methyl iodide
74-88-4

methyl iodide

1-methyl-1H-indole-2,3-dione
2058-74-4

1-methyl-1H-indole-2,3-dione

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 12h;
100%
With potassium carbonate99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;98%
indole-2,3-dione
91-56-5

indole-2,3-dione

isatoic anhydride
118-48-9

isatoic anhydride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h; Inert atmosphere; Photolysis;100%
With tert.-butylhydroperoxide In water at 100℃; for 2h; Green chemistry;90%
With diphenyl diselenide; dihydrogen peroxide In N,N-dimethyl-formamide; acetonitrile at 25℃; for 8h; Solvent; Temperature; Reagent/catalyst; Time; Baeyer-Villiger Ketone Oxidation; Schlenk technique; Green chemistry;88%
indole-2,3-dione
91-56-5

indole-2,3-dione

1H-Indazole-3-carboxylic acid
4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydroxide In water at 20 - 50℃; for 1.5h;
Stage #2: With sulfuric acid; sodium nitrite In water at 0℃; for 1h;
Stage #3: With hydrogenchloride; tin(ll) chloride In water for 1.16667h;
100%
With sodium hydroxide; sulfuric acid; sulfur dioxide; sodium nitrite Reagens 4: Zinnchloruer;
With sulfuric acid; sodium nitrite danach SnCl2;
2-oxoindole
59-48-3

2-oxoindole

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

indole-2,3-dione

isoindigo
476-34-6

isoindigo

Conditions
ConditionsYield
With hydrogenchloride In acetic acid Heating;100%
With zirconium(IV) chloride In ethanol Reagent/catalyst; Solvent; Temperature; Reflux;91%
With hydrogenchloride In water; acetic acid for 3h; Reflux;88%
N,N'-diacetylpiperazin-2,5-dione
3027-05-2

N,N'-diacetylpiperazin-2,5-dione

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

indole-2,3-dione

3,6-bis(2-oxo-1,2-dihydroindol-3-ylidene)piperazine-2,5-dione
117563-29-8

3,6-bis(2-oxo-1,2-dihydroindol-3-ylidene)piperazine-2,5-dione

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 4h;100%
With triethylamine In N,N-dimethyl-formamide at 20℃; Knoevenagel condensation;90%
With triethylamine In N,N-dimethyl-formamide at 40℃; for 5h;
1-bromo-butane
109-65-9

1-bromo-butane

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

indole-2,3-dione

N-butylisatin
4290-91-9

N-butylisatin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;100%
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation;93%
With potassium carbonate In N,N-dimethyl-formamide for 0.05h; microwave irradiation;90%
indole-2,3-dione
91-56-5

indole-2,3-dione

ethyl iodide
75-03-6

ethyl iodide

N-ethylisatin
4290-94-2

N-ethylisatin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;100%
With potassium carbonate In N,N-dimethyl-formamide for 0.05h; microwave irradiation;90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;90%
indole-2,3-dione
91-56-5

indole-2,3-dione

ethyl bromoacetate
105-36-2

ethyl bromoacetate

(1-ethoxycarbonylmethyl)isatin
41042-21-1

(1-ethoxycarbonylmethyl)isatin

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With calcium hydride In N,N-dimethyl-formamide at 100℃; for 1h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 100℃; for 4h;
100%
Stage #1: indole-2,3-dione With aluminum oxide; potassium fluoride In acetonitrile for 0.0833333h;
Stage #2: ethyl bromoacetate In acetonitrile for 21h; Reflux;
97%
With KF-Celite In 2-methyltetrahydrofuran for 4h; Reflux; chemoselective reaction;93%
indole-2,3-dione
91-56-5

indole-2,3-dione

(3-Methyl-7-β-phenylethylxanthinyl-8) thioacetic hydrazide
107608-60-6

(3-Methyl-7-β-phenylethylxanthinyl-8) thioacetic hydrazide

(3-Methyl-2,6-dioxo-7-phenethyl-2,3,6,7-tetrahydro-1H-purin-8-ylsulfanyl)-acetic acid [2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide
107608-68-4

(3-Methyl-2,6-dioxo-7-phenethyl-2,3,6,7-tetrahydro-1H-purin-8-ylsulfanyl)-acetic acid [2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide

Conditions
ConditionsYield
With acetic acid In ethanol Heating;100%
indole-2,3-dione
91-56-5

indole-2,3-dione

propargyl bromide
106-96-7

propargyl bromide

1-prop-2-ynyl-1H-indole-2,3-dione
4290-87-3

1-prop-2-ynyl-1H-indole-2,3-dione

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide for 0.333333h; Cooling with ice;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;
100%
With potassium carbonate In N,N-dimethyl-formamide; toluene at 50℃; for 0.0833333h; Solvent; Time; Microwave irradiation;97.2%
With KF-Celite In 2-methyltetrahydrofuran for 3h; Reflux; chemoselective reaction;95%
4'-ethyl-1',4',7',8'-tetrahydro-4'-hydroxy-3'H,10'H-spiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione
102978-41-6

4'-ethyl-1',4',7',8'-tetrahydro-4'-hydroxy-3'H,10'H-spiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione

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

indole-2,3-dione

7-carboxylic acid 20(R,S)-camptothecin

7-carboxylic acid 20(R,S)-camptothecin

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 105℃; for 15h;100%
N-Ethylmethylamine
624-78-2

N-Ethylmethylamine

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

indole-2,3-dione

(2-Amino-phenyl)-oxo-acetic acid; compound with ethyl-methyl-amine

(2-Amino-phenyl)-oxo-acetic acid; compound with ethyl-methyl-amine

Conditions
ConditionsYield
In water Heating;100%
indole-2,3-dione
91-56-5

indole-2,3-dione

di-n-propylamine
142-84-7

di-n-propylamine

(2-Amino-phenyl)-oxo-acetic acid; compound with dipropyl-amine

(2-Amino-phenyl)-oxo-acetic acid; compound with dipropyl-amine

Conditions
ConditionsYield
In water Heating;100%
indole-2,3-dione
91-56-5

indole-2,3-dione

diethylamine
109-89-7

diethylamine

(2-Amino-phenyl)-oxo-acetic acid; compound with diethyl-amine

(2-Amino-phenyl)-oxo-acetic acid; compound with diethyl-amine

Conditions
ConditionsYield
In water Heating;100%
indole-2,3-dione
91-56-5

indole-2,3-dione

diisopropylamine
108-18-9

diisopropylamine

(2-Amino-phenyl)-oxo-acetic acid; compound with diisopropyl-amine

(2-Amino-phenyl)-oxo-acetic acid; compound with diisopropyl-amine

Conditions
ConditionsYield
In water Heating;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

indole-2,3-dione

1-tert-butoxycarbonylisatin
160858-75-3

1-tert-butoxycarbonylisatin

Conditions
ConditionsYield
With dmap Inert atmosphere;100%
With dmap In tetrahydrofuran at 20℃; for 5h;100%
With dmap In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;96%
indole-2,3-dione
91-56-5

indole-2,3-dione

acetone
67-64-1

acetone

A

(R)-3-hydroxy-3-(2'-oxopropyl)indolin-2-one

(R)-3-hydroxy-3-(2'-oxopropyl)indolin-2-one

B

(S)-3-(2-oxopropyl)-3-hydroxyindolin-2-one

(S)-3-(2-oxopropyl)-3-hydroxyindolin-2-one

Conditions
ConditionsYield
With D-Pro-L-β3-hPhg-OBn; water at -15℃; for 16h; optical yield given as %ee;A 100%
B n/a
With Na(1+)-Montmorillonite-entrapped N-(2-thiophenesulfonyl)-L-prolinamide; trifluoroacetic acid In water at 20℃; for 40h; optical yield given as %ee;A 99%
B n/a
With 1,1′-binaphthyl-2,2′-diamine-L-prolinamide In neat (no solvent) at 25℃; for 24h; Solvent; Temperature; Reagent/catalyst; stereoselective reaction;A n/a
B 98%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

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

indole-2,3-dione

1H-indole-2,3-dione 3-(O-methyloxime)
107976-78-3

1H-indole-2,3-dione 3-(O-methyloxime)

Conditions
ConditionsYield
With dipotassium hydrogenphosphate In methanol at 20℃; for 2h;100%
With sodium hydrogencarbonate In methanol; water at 50℃; for 8h;92%
With sodium hydrogencarbonate In methanol; water at 20℃; for 1.08333h;80%
2-(bromomethyl)-5-(trifluoromethyl)furan
17515-77-4

2-(bromomethyl)-5-(trifluoromethyl)furan

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

indole-2,3-dione

1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1H-indole-2,3-dione
1019767-70-4

1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1H-indole-2,3-dione

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)furan In N,N-dimethyl-formamide at 20℃;
100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Concentration; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;100%
With potassium carbonate In dimethyl sulfoxide at 20 - 30℃;96.4%
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)furan In N,N-dimethyl-formamide at 20℃; for 1h;
32%
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 0.416667h; Inert atmosphere; Large scale;
Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)furan In N,N-dimethyl-formamide at 45 - 54℃; for 2h; Inert atmosphere; Large scale;
Sesamol
533-31-3

Sesamol

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

indole-2,3-dione

3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one
1019771-89-1

3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Conditions
ConditionsYield
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 4℃; for 2h; Industry scale;
Stage #2: indole-2,3-dione In tetrahydrofuran at -5 - 3℃; Industry scale;
Stage #3: With water; ammonium chloride In tetrahydrofuran at 3 - 4℃; Industry scale;
100%
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 2.5h;
Stage #2: indole-2,3-dione In tetrahydrofuran at 0 - 20℃; for 19h;
98%
With potassium carbonate In tetrahydrofuran for 17h; Solvent; Inert atmosphere;
With triethylamine In tert-butyl methyl ether at 25℃; for 15h; Inert atmosphere;
In water at 20℃;
1-bromo-2-cyclohexylethane
1647-26-3

1-bromo-2-cyclohexylethane

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

indole-2,3-dione

1-(2-cyclohexylethyl)-isatin
1048973-34-7

1-(2-cyclohexylethyl)-isatin

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: 1-bromo-2-cyclohexylethane In N,N-dimethyl-formamide at 20℃;
100%
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: 1-bromo-2-cyclohexylethane In N,N-dimethyl-formamide at 20℃;
100%
indole-2,3-dione
91-56-5

indole-2,3-dione

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

malononitrile
109-77-3

malononitrile

diethyl (3-(dicyanomethyl)-2-oxoindolin-3-yl)phosphonate
1210948-52-9

diethyl (3-(dicyanomethyl)-2-oxoindolin-3-yl)phosphonate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.283333h; Reagent/catalyst; Time; Solvent; Ionic liquid; Large scale;100%
With ZnO nano-rods at 20℃; for 1h; Neat (no solvent);98%
at 50℃; for 2h; neat (no solvent);81%
indole-2,3-dione
91-56-5

indole-2,3-dione

ethyl 2-amino-2-hydrazonoacetate

ethyl 2-amino-2-hydrazonoacetate

C12H10N4O2
1394237-93-4

C12H10N4O2

Conditions
ConditionsYield
Stage #1: indole-2,3-dione; ethyl 2-amino-2-hydrazonoacetate In ethanol at 20℃; Reflux; Inert atmosphere;
Stage #2: In bromobenzene for 24h; Inert atmosphere; Reflux;
100%
5-(1',2',3',4'-tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide

5-(1',2',3',4'-tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide

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

indole-2,3-dione

5-(1',2',3',4'-tetrahydroxybutyl)-2-methyl-N-(2-oxoindolin-3-ylidene)furan-3-carbohydrazide

5-(1',2',3',4'-tetrahydroxybutyl)-2-methyl-N-(2-oxoindolin-3-ylidene)furan-3-carbohydrazide

Conditions
ConditionsYield
With acetic acid In ethanol for 1h; Reflux;100%
3-amino-2-methyl-4-oxoquinazoline
1898-06-2

3-amino-2-methyl-4-oxoquinazoline

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

indole-2,3-dione

indolo[3',2':3,4]pyridazino[6,1-b]quinazolin-7(14H)-one
101507-96-4

indolo[3',2':3,4]pyridazino[6,1-b]quinazolin-7(14H)-one

Conditions
ConditionsYield
With 2,3,4,5,6-pentafluorophenol at 80℃; for 2h;100%
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

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

indole-2,3-dione

methyl 4-((2,3-dioxoindolin-1-yl)methyl)benzoate
380567-18-0

methyl 4-((2,3-dioxoindolin-1-yl)methyl)benzoate

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h;
Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide; mineral oil at 25℃; for 12h;
100%
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 48.0833h;52%
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;
Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide; mineral oil
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide for 0.75h;
Stage #2: Methyl 4-(bromomethyl)benzoate With potassium iodide In N,N-dimethyl-formamide at 80℃;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide
indole-2,3-dione
91-56-5

indole-2,3-dione

1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene
88116-02-3

1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene

(1-(2-benzenesulfonylmethyl-benzyl)-1H‑indole-2,3-dione)

(1-(2-benzenesulfonylmethyl-benzyl)-1H‑indole-2,3-dione)

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h;
Stage #2: 1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene In N,N-dimethyl-formamide at 20℃; for 3h;
100%
indole-2,3-dione
91-56-5

indole-2,3-dione

7-bromoisatin
20780-74-9

7-bromoisatin

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 24h;100%

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