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5-Cyanoindole
Cas No: 15861-24-2
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High purity Various Specifications 5-Cyanoindole CAS:15861-24-2
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5-Cyanoindole
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5-Cyanoindole
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
5-Cyanoindole CAS: 15861-24-2
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USD $ 1.0-2.0 / Metric Ton 5 Metric Ton 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier
5-Cyanoindole CAS NO.15861-24-2
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USD $ 1.0-3.0 / Kilogram 1 Kilogram 10 Kilogram/Day Hebei yanxi chemical co.,LTD. Contact Supplier
5-Cyanoindole
Cas No: 15861-24-2
USD $ 12.0-12.0 / Gram 1 Gram 100 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier
99%min 5-Cyanoindole factory price
Cas No: 15861-24-2
USD $ 10.0-10.0 / Gram 1 Gram 1000 Kilogram/Month Shenzhen Tianyuan Pharmaceutical Technology Co., Ltd Contact Supplier

15861-24-2 Usage

Purification Methods

Dissolve the nitrile in 95% EtOH, boil it in the presence of charcoal, filter, evaporate to a small volume and add enough H2O to cause crystallisation and cool. Recrystallise it directly from aqueous EtOH and dry it in a vacuum. UV has at max 276 nm (log 3.6) in MeOH. [Lindwall & Mantell J Org Chem 18 345 1953, 20 1458 1955, Thesing at al. Chem Ber 95 2205 1962, NMR: Lallemend & Bernath Bull Soc Chim Fr 4091 1970, Beilstein 22/3 V 45.]

Uses

Inhibitor of enzyme.

Chemical Properties

Off-White Crystalline Powder

Uses

? ;Reactant for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction1? ;Reactant for chemoselective and regioselective preparation of benzoyl indoles2? ;Reactant for preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM3? ;Reactant for preparation of 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant4? ;Reactant for preparation of vinylindoles by hydroarylation of alkynes using indium bromi
InChI:InChI=1/C9H6N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H

15861-24-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (B21810)  Indole-5-carbonitrile, 98+%    15861-24-2 1g 742.0CNY Detail
Alfa Aesar (B21810)  Indole-5-carbonitrile, 98+%    15861-24-2 5g 2158.0CNY Detail
Alfa Aesar (B21810)  Indole-5-carbonitrile, 98+%    15861-24-2 25g 9172.0CNY Detail
Aldrich (C92006)  Indole-5-carbonitrile  99% 15861-24-2 C92006-5G 1,577.16CNY Detail
Aldrich (C92006)  Indole-5-carbonitrile  99% 15861-24-2 C92006-10G 2,788.11CNY Detail

15861-24-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Cyanoindole

1.2 Other means of identification

Product number -
Other names 1H-Indole-5-carbonitrile

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:15861-24-2 SDS

15861-24-2Synthetic route

zinc(II) cyanide
557-21-1

zinc(II) cyanide

5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 40℃; for 18h; Inert atmosphere;99%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 110℃; for 12h; Inert atmosphere;90%
5-cyanoindole-3-carboxylic acid
174500-89-1

5-cyanoindole-3-carboxylic acid

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In ethanol at 140℃; Schlenk technique;99%
4-amino-3-ethynylbenzonitrile
412947-51-4

4-amino-3-ethynylbenzonitrile

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With P(p-C6H4F)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In N,N-dimethyl-formamide at 85℃; for 2h;98%
With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In pyridine at 90℃; for 0.5h; Inert atmosphere; regioselective reaction;98%
With pyridine; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 90℃; for 0.5h; Catalytic behavior; Inert atmosphere; regioselective reaction;98%
1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile
475102-10-4

1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
In various solvent(s) at 150℃; for 0.0833333h; microwave irradiation;98%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.0833333h; Product distribution / selectivity; Microwave irradiation;98%
With 2,2,2-trifluoroethanol at 150℃; for 1h; Product distribution / selectivity; Microwave irradiation;98%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.0833333h; Product distribution / selectivity; Microwave irradiation;98%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
palladium diacetate; PS-triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 0.833333h; Irradiation; microwave;96%
3-methyl-4-nitrobenzonitrile
96784-54-2

3-methyl-4-nitrobenzonitrile

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 3-methyl-4-nitrobenzonitrile; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In dichloromethane at 50 - 55℃; for 8h; Large scale; Green chemistry;
Stage #2: With iron; acetic acid In methanol at 0 - 55℃; for 8h; Reagent/catalyst; Solvent; Temperature; Large scale; Green chemistry;
96%
Stage #1: 3-methyl-4-nitrobenzonitrile; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 2.5h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere;
Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis;
71%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

sodium cyanide
143-33-9

sodium cyanide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h; Rosenmund-von Braun reaction;95%
Stage #1: 5-bromo-1H-indole; sodium cyanide With potassium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 110℃; for 24h;
Stage #2: With ammonia In water; ethyl acetate; toluene at 25℃; for 0.166667h;
95%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) at 115℃; for 2h; Substitution;76%
sodium cyanide
773837-37-9

sodium cyanide

5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile for 2.5h; Reflux;95%
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;53%
5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

carbon dioxide
124-38-9

carbon dioxide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) oxide; phenylsilane; ammonia In 1-methyl-pyrrolidin-2-one at 180℃; under 2280.15 Torr; for 24h; Sealed tube; chemoselective reaction;94%
With ammonia; hydrogen; nickel dibromide In N,N-dimethyl-formamide at 160℃; for 10h; Sealed tube;92 %Chromat.
1-benzyl-1H-indole-5-carbonitrile
80531-13-1

1-benzyl-1H-indole-5-carbonitrile

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With potassium tert-butylate; oxygen; dimethyl sulfoxide at 0℃; for 0.333333h;93%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

1H-indol-5-yl methanesulfonate
128810-31-1

1H-indol-5-yl methanesulfonate

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate In water; tert-butyl alcohol at 80℃; for 18h; Inert atmosphere;93%
5-Cyano-1-(p-toluenesulfonyl)indole
32685-23-7

5-Cyano-1-(p-toluenesulfonyl)indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;93%
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 2h; Inert atmosphere;87%
With water; sodium hydroxide In methanol at 60℃; for 2h;84%
4-cyanopyridine N-oxide
14906-59-3

4-cyanopyridine N-oxide

5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; trifluoroacetic acid; sodium iodide; nickel dichloride; zinc In N,N-dimethyl acetamide at 60℃; for 36h;93%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 10h; Schlenk technique; Inert atmosphere;92%
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In water; tert-butyl alcohol at 85℃; for 8h; Inert atmosphere;85%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 24h;76%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; sodium carbonate; triethylamine In water; acetonitrile at 70℃; for 18h;91%
5-cyano-indole-1-sulfonic acid dimethylamide

5-cyano-indole-1-sulfonic acid dimethylamide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; Electrolysis;90%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

copper(l) cyanide

copper(l) cyanide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 20h; Heating;88%
In 1-methyl-pyrrolidin-2-one for 3h; Inert atmosphere; Reflux;82%
With 1-methyl-pyrrolidin-2-one at 155℃; for 6h; Inert atmosphere;80%
In 1-methyl-pyrrolidin-2-one at 100 - 200℃; for 1h; Microwave irradiation;
In 1-methyl-pyrrolidin-2-one at 230℃; for 5h;
potassium cyanide

potassium cyanide

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine In acetonitrile at 200℃; for 1h; Microwave irradiation; Inert atmosphere;88%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

copper(I) cyanide
544-92-3

copper(I) cyanide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole; copper(I) cyanide In 1-methyl-pyrrolidin-2-one for 18h; Heating / reflux;
Stage #2: With ammonia In 1-methyl-pyrrolidin-2-one; water
82%
In 1-methyl-pyrrolidin-2-one for 0.5h; Rosenmund-von Braun reaction; microwave irradiation;79%
With 1-methyl-pyrrolidin-2-one for 4.5h; Heating;72.6%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With [2,2]bipyridinyl; aluminum (III) chloride; nickel(II) acetylacetonate; zinc(II) oxide In 1,2-dimethoxyethane at 145℃; for 12h;79%
5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

copper(l) cyanide

copper(l) cyanide

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With copper(l) iodide; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere;77%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

2,4,6-tris((1H-indol-5-yl)oxy)-1,3,5-triazine

2,4,6-tris((1H-indol-5-yl)oxy)-1,3,5-triazine

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;76%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6.5h; Schlenk technique; Inert atmosphere; Sealed tube;72%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6.5h; Inert atmosphere; Sealed tube;72%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With ISOPROPYLAMIDE; sodium carbonate at 110℃; for 15h;68%
5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 140℃; for 48h; Inert atmosphere;67%
With copper(l) iodide; triphenylphosphine; trichlorophosphate at 140℃; for 24h; Inert atmosphere;66%
Stage #1: 5-iodo-1H-indole; formamide With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 20℃; Inert atmosphere;
Stage #2: With trichlorophosphate at 135 - 140℃; for 24h; Inert atmosphere;
50 %Chromat.
With zinc diacetate; nixantphos In 1-methyl-pyrrolidin-2-one at 140℃; for 24h; Inert atmosphere;86 %Chromat.
5-aminomethylindole
81881-74-5

5-aminomethylindole

A

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

B

1H-indole-5-carboxaldehyde
1196-69-6

1H-indole-5-carboxaldehyde

Conditions
ConditionsYield
With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen In N,N-dimethyl-formamide at 120℃; under 760.051 Torr; for 2h; Sealed tube;A 67%
B 10%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

1H-indol-5-yl methanesulfonate
128810-31-1

1H-indol-5-yl methanesulfonate

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With dmap; nickel(II) bromide dimethoxyethane; 1,4-di(diphenylphosphino)-butane; zinc In acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere;65%
indoline-5-carbonitrile
15861-23-1

indoline-5-carbonitrile

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With tetrasodium cobalt(II) 4,4',4'',4'''-tetrasulphophthalocyanine In water; ethyl acetate at 20℃; for 36h; Irradiation; Green chemistry;65%
With potassium tert-butylate In o-xylene at 140℃; for 36h; Inert atmosphere;10%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

acetonitrile
75-05-8

acetonitrile

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Conditions
ConditionsYield
With 1,10-Phenanthroline; hexakis(acetonitrile)nickel(II) tetrafluoroborate; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene at 80℃; for 24h;53%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

5-aminomethylindole
81881-74-5

5-aminomethylindole

Conditions
ConditionsYield
With ammonia; hydrogen; nickel In methanol; water100%
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 150℃; for 3h; Inert atmosphere; Autoclave;98%
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Inert atmosphere; Reflux;94%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

4-(5-cyano-1H-indol-1-yl)butanoic acid
1229952-77-5

4-(5-cyano-1H-indol-1-yl)butanoic acid

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile; Ethyl 4-bromobutyrate With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In dichloromethane at 20℃; for 6h;
Stage #2: With hydrogenchloride In water
100%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

iodobenzene
591-50-4

iodobenzene

1-phenyl-1H-indole-5-carbonitrile

1-phenyl-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h;99%
With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux;98%
With copper(l) iodide; (1R,2R)-1,2-diaminocyclohexane; potassium carbonate In water at 80℃; for 18h; Buchwald N-arylation;91%
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;78%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Ullmann-type N-arylation;56%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

(1E,4E)-1-phenyl-1,4-hexadien-3-one
91897-73-3

(1E,4E)-1-phenyl-1,4-hexadien-3-one

C21H18N2O
1128087-20-6

C21H18N2O

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile; (1E,4E)-1-phenyl-1,4-hexadien-3-one With 2,4-dinitrobenzenesulfonic acid In acetonitrile at 0℃; for 4.5h; Friedel-Crafts alkylation; Inert atmosphere;
Stage #2: In methanol at -20 - 20℃; for 48h; Inert atmosphere;
99%
1-ethenyl-2-pyrrolidinone
88-12-0

1-ethenyl-2-pyrrolidinone

1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

3-(1-(2-oxopyrrolidin-1-yl)ethyl)-1H-indole-5-carbonitrile
1262894-55-2

3-(1-(2-oxopyrrolidin-1-yl)ethyl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 40℃; for 6h; regioselective reaction;99%
With tris(p-bromophenyl)ammoniumyl hexachloroantimonate In chloroform at 20℃; for 0.5h; Friedel-Crafts Alkylation; Green chemistry; regiospecific reaction;66%
With tris(p-bromophenylammoniumyl) hexachloroantimonate In chloroform at 20℃; for 0.5h; Friedel-Crafts Alkylation; Green chemistry; regioselective reaction;66%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

methyl oct-1-en-3-yl carbonate
95151-36-3

methyl oct-1-en-3-yl carbonate

(R)-1-(oct-1-en-3-yl)-1H-indole-5-carbonitrile

(R)-1-(oct-1-en-3-yl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C39H51N2O3P In acetonitrile at 100℃; for 36h; enantioselective reaction;99%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5-Cyano-1-(p-toluenesulfonyl)indole
32685-23-7

5-Cyano-1-(p-toluenesulfonyl)indole

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 20℃; for 1h;98%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 1h;98%
With tetrabutylammomium bromide; sodium hydroxide In toluene at 20℃; for 1h;98.1%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

benzaldehyde
100-52-7

benzaldehyde

3-(hydroxyphenylmethyl)indole-5-carbonitrile
787631-74-7

3-(hydroxyphenylmethyl)indole-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 96h;98%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

3-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-1H-indole-5-carbonitrile
1150561-06-0

3-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; water at 20℃; for 16h; Friedel-Crafts type alkylation;98%
With TMG In dichloromethane at 20℃;
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

tert-butyl (5-cyano-1H-indol-1-yl)acetate
1229608-56-3

tert-butyl (5-cyano-1H-indol-1-yl)acetate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 16h; Reflux;98%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

1-(2-nitrobenzoyl)-1H-indole-5-carbonitrile

1-(2-nitrobenzoyl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile With tetra(n-butyl)ammonium hydrogensulfate; sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-nitrobenzyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
98%
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

Isobutyl bromide
78-77-3

Isobutyl bromide

1-isobutyl-1H-indole-5-carbonitrile

1-isobutyl-1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50℃; for 1h; Inert atmosphere;
Stage #2: Isobutyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;
98%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

2-oxo-3,3′-biindoline-5,5′-dicarbonitrile
1414941-97-1

2-oxo-3,3′-biindoline-5,5′-dicarbonitrile

Conditions
ConditionsYield
With pyridine; bis-[(trifluoroacetoxy)iodo]benzene; bis(pinacol)diborane In toluene at 60℃; for 11h; Reagent/catalyst;97.9%
With morpholine; copper(I) oxide; tert.-butylhydroperoxide; oxygen In chloroform at 20℃; under 760.051 Torr; for 18h; regioselective reaction;56%
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; oxygen; silver nitrate; benzoic acid at 65℃; for 48h;37%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; benzoic acid In acetonitrile at 65℃; for 72h;15%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

benzyl halide

benzyl halide

1-benzyl-1H-indole-5-carbonitrile
80531-13-1

1-benzyl-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With sodium hydride; potassium iodide In mineral oil at 0 - 80℃;97.3%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-formyl-1H-indole-5-carbonitrile
17380-18-6

3-formyl-1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.0833333h; Inert atmosphere; Cooling with ice;
Stage #2: 1H-indole-5-carbonitrile at 25℃; Inert atmosphere; Cooling with ice;
Stage #3: With potassium hydroxide In water at 25℃; Reflux;
97%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.333333h; Vilsmeier formylation;
Stage #2: 1H-indole-5-carbonitrile at 35℃; for 1h;
94%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 0.333333h;
Stage #2: 1H-indole-5-carbonitrile at 0 - 30℃; for 3h;
Stage #3: With sodium hydroxide In water pH=8 - 9; Reflux;
92.19%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile
475102-10-4

1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 24h;97%
With dmap In dichloromethane at 20℃; for 0.75h;96.7%
Stage #1: 1H-indole-5-carbonitrile With dmap In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate for 2h;
96%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

4-methoxybenzyl halide

4-methoxybenzyl halide

1-(4-methoxybenzyl)-1H-indole-5-carbonitrile

1-(4-methoxybenzyl)-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With sodium hydride; potassium iodide In mineral oil at 0 - 80℃;96.1%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-benzenesulfonyl-1H-indole-5-carbonitrile
144340-21-6

1-benzenesulfonyl-1H-indole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 0.5h; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In water; toluene at 20℃; for 25h; Inert atmosphere;
96%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 25h; Inert atmosphere;96%
Stage #1: 1H-indole-5-carbonitrile With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃;
86%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

3-thiocyanato-1H-indole-5-carbonitrile
1044513-31-6

3-thiocyanato-1H-indole-5-carbonitrile

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In methanol at 25℃; for 0.25h;96%
With Oxone In methanol at 20℃;95%
With Selectfluor In acetonitrile at 20℃; for 0.166667h;92%
With Selectfluor In acetonitrile at 20℃; for 2h; Inert atmosphere;60%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

(R)-methyl 2-(5-cyano-1H-indol-3-yl)-3,3,3-trifluoro-2-hydroxypropanoate
1241940-64-6

(R)-methyl 2-(5-cyano-1H-indol-3-yl)-3,3,3-trifluoro-2-hydroxypropanoate

Conditions
ConditionsYield
With (R)-3,3'-bis(1-naphthyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl posphate alenyl-2,2'-diol In toluene at -78℃; for 94h; Friedel-Crafts alkylation; optical yield given as %ee; enantioselective reaction;96%
Stage #1: 1H-indole-5-carbonitrile With C78H78N12O6 In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 3,3,3-trifluoropyruvate In tetrahydrofuran at -20℃; for 12h; Inert atmosphere; enantioselective reaction;
81%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

N'-hydroxy-1H-indole-5-carboximidamide
163797-89-5

N'-hydroxy-1H-indole-5-carboximidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In ethanol at 80℃;96%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 3h; Reflux;90%
With ethanol; hydroxylamine hydrochloride; triethylamine at 0 - 80℃;82.3%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

7-ethoxy-4,7-dioxoheptanoic acid chloride
1506-56-5

7-ethoxy-4,7-dioxoheptanoic acid chloride

ethyl 7-(5-cyano-1H-indol-1-yl)-4,7-dioxoheptanoate

ethyl 7-(5-cyano-1H-indol-1-yl)-4,7-dioxoheptanoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 72h; Inert atmosphere;96%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

N-thiocyanatodibenzenesulfonimide

N-thiocyanatodibenzenesulfonimide

3-thiocyanato-1H-indole-5-carbonitrile
1044513-31-6

3-thiocyanato-1H-indole-5-carbonitrile

Conditions
ConditionsYield
In acetonitrile for 0.166667h;96%
1H-indole-5-carbonitrile
15861-24-2

1H-indole-5-carbonitrile

S,S-dimethyl-S-(trifluoroacetoxy)sulfonium trifluoroacetate
57738-66-6

S,S-dimethyl-S-(trifluoroacetoxy)sulfonium trifluoroacetate

(5-cyanoindol-3-yl)dimethylsulfonium perchlorate
1440957-20-9

(5-cyanoindol-3-yl)dimethylsulfonium perchlorate

Conditions
ConditionsYield
Stage #1: 1H-indole-5-carbonitrile; S,S-dimethyl-S-(trifluoroacetoxy)sulfonium trifluoroacetate In dichloromethane at -78 - 20℃; Inert atmosphere;
Stage #2: With lithium perchlorate In dichloromethane; water at 20℃; Inert atmosphere; Cooling with ice;
95.5%
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