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4769-96-4 Usage

Chemical Properties

yellow to brown-yellow powder

Check Digit Verification of cas no

The CAS Registry Mumber 4769-96-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,6 and 9 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4769-96:
(6*4)+(5*7)+(4*6)+(3*9)+(2*9)+(1*6)=134
134 % 10 = 4
So 4769-96-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H6N2O2/c11-10(12)7-2-1-6-3-4-9-8(6)5-7/h1-5,9H

4769-96-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A12927)  6-Nitroindole, 97%   

  • 4769-96-4

  • 1g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (A12927)  6-Nitroindole, 97%   

  • 4769-96-4

  • 5g

  • 578.0CNY

  • Detail
  • Alfa Aesar

  • (A12927)  6-Nitroindole, 97%   

  • 4769-96-4

  • 25g

  • 2174.0CNY

  • Detail

4769-96-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Nitroindole

1.2 Other means of identification

Product number -
Other names 6-Nitro-1H-indole

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:4769-96-4 SDS

4769-96-4Synthetic route

6-nitroindoline
19727-83-4

6-nitroindoline

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With oxygen; salcomine In methanol at 25℃; for 5h;92%
With manganese(IV) oxide In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;92%
With isolated cobalt single atom sites stabilized on an ordered porous nitrogen doped carbon matrix In 1,3,5-trimethyl-benzene at 120℃; for 8h; Schlenk technique;92%
C18H20N2O4

C18H20N2O4

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
In ethylene glycol at 170℃; Retro Diels-Alder reaction; Inert atmosphere;92%
2-ethynyl-5-nitroaniline
1245255-75-7

2-ethynyl-5-nitroaniline

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With [cyclopentadienylruthenium(II) bis-(2-diphenylphosphino-6-t-butylpyridine)(acetonitrile)]hexafluorophosphate In tetrahydrofuran-d8 at 70℃; for 2h; Sealed tube;92%
6-nitroindoline
19727-83-4

6-nitroindoline

A

6-nitroindole
4769-96-4

6-nitroindole

B

1-hydroxy-6-introindole
354807-12-8

1-hydroxy-6-introindole

Conditions
ConditionsYield
With sodium tungstate; dihydrogen peroxide In methanol; water at 20℃; for 7h;A 7%
B 79%
C11H14N2O4

C11H14N2O4

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With Amberlyst 15 In 2-methyltetrahydrofuran at 100℃; for 0.75h; Microwave irradiation;70%
sodium methylate
124-41-4

sodium methylate

1-methoxy-6-nitroindole
125812-46-6

1-methoxy-6-nitroindole

A

6-nitroindole
4769-96-4

6-nitroindole

B

2-methoxy-6-nitroindole

2-methoxy-6-nitroindole

C

3-methoxy-6-nitroindole

3-methoxy-6-nitroindole

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide for 0.0833333h; Heating;A 57%
B 22%
C 6%
1-methoxy-6-nitroindole
125812-46-6

1-methoxy-6-nitroindole

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

6-nitroindole
4769-96-4

6-nitroindole

B

2-methylthio-6-nitroindole

2-methylthio-6-nitroindole

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide for 1h; Heating;A 54%
B 13%
2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

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

N,N-dimethyl-formamide dimethyl acetal

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Stage #1: 2,4-dinitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 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;
52%
diethyl malonate
105-53-3

diethyl malonate

1-methoxy-6-nitroindole
125812-46-6

1-methoxy-6-nitroindole

A

6-nitroindole
4769-96-4

6-nitroindole

B

diethyl 2-(6-nitroindol-3-yl)methylmalonate
22980-05-8

diethyl 2-(6-nitroindol-3-yl)methylmalonate

C

3-methoxy-6-nitroindole

3-methoxy-6-nitroindole

Conditions
ConditionsYield
With potassium hydride In N,N-dimethyl-formamide for 0.0833333h; Heating;A 20%
B 40%
C 5%
sodium cyanide
143-33-9

sodium cyanide

1-methoxy-6-nitroindole
125812-46-6

1-methoxy-6-nitroindole

A

6-nitroindole
4769-96-4

6-nitroindole

B

7-cyano-6-nitroindole

7-cyano-6-nitroindole

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide for 1h; Heating;A 4%
B 15%
6-Nitro-1H-indole-2-carboxylic Acid
10242-00-9

6-Nitro-1H-indole-2-carboxylic Acid

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With quinoline; copper(II) oxide
6-nitro-1H-indole-3-carboxylic acid
10242-03-2

6-nitro-1H-indole-3-carboxylic acid

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With quinoline at 180℃;
N-chloromethylsulfonyl-6-nitroindoline
143032-50-2

N-chloromethylsulfonyl-6-nitroindoline

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h;
acetaldehyde-(3-nitro-phenylhydrazone)
23622-32-4

acetaldehyde-(3-nitro-phenylhydrazone)

A

6-nitroindole
4769-96-4

6-nitroindole

B

4-nitro-1H-indoIe
4769-97-5

4-nitro-1H-indoIe

Conditions
ConditionsYield
GIPKh-115 In acetonitrile at 200 - 320℃; (g) phase;
GIPKh-115 In acetonitrile at 180 - 320℃; (g) phase. Object of study: effect of electronic factors;
1-hydroxy-6-introindole
354807-12-8

1-hydroxy-6-introindole

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / methanol / 20 °C
2: 4 percent / dimethylformamide; H2O / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 96 percent / methanol / 20 °C
2: 57 percent / dimethylformamide; methanol / 0.08 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 96 percent / methanol / 20 °C
2: 20 percent / KH (35 percent in mineral oil) / dimethylformamide / 0.08 h / Heating
View Scheme
1-indoline
496-15-1

1-indoline

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; nitric acid / <5
2: maleic acid-anhydride; palladium; water
View Scheme
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; nitric acid / <5
2: tetrachloro-<1,4>benzoquinone; xylene
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; sulfuric acid / 0 - 20 °C
2: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; sulfuric acid / 0 - 20 °C
2: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
View Scheme
indole-3-carboxylic acid ethyl ester
776-41-0

indole-3-carboxylic acid ethyl ester

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; HNO3
2: aqueous KOH
3: quinoline / 180 °C
View Scheme
6-nitro-1H-indole-2-carboxylic acid ethyl ester
16792-45-3

6-nitro-1H-indole-2-carboxylic acid ethyl ester

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq.-ethanolic KOH
2: copper (II)-oxide; quinoline
View Scheme
6-nitro-indole-3-carboxylic acid ethyl ester
91090-95-8

6-nitro-indole-3-carboxylic acid ethyl ester

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KOH
2: quinoline / 180 °C
View Scheme
ethyl 2-[2-(3-nitrophenyl)hydrazinylidene]propanoate
134747-25-4

ethyl 2-[2-(3-nitrophenyl)hydrazinylidene]propanoate

6-nitroindole
4769-96-4

6-nitroindole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: polyphosphoric acid
2: aq.-ethanolic KOH
3: copper (II)-oxide; quinoline
View Scheme
6-nitroindole
4769-96-4

6-nitroindole

6-amino-1H-indole
5318-27-4

6-amino-1H-indole

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 2587.7 Torr;100%
100%
With silver tetrafluoroborate; 4,4'-Dimethoxy-2,2'-bipyridin; potassium tert-butylate; hydrogen In 1,4-dioxane at 80℃; under 30003 Torr; for 48h; Autoclave;94%
6-nitroindole
4769-96-4

6-nitroindole

methyl iodide
74-88-4

methyl iodide

1-methyl-6-nitro-indole
99459-48-0

1-methyl-6-nitro-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.166667h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0℃;
100%
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.166667h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;98%
6-nitroindole
4769-96-4

6-nitroindole

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-[4-(methylphenyl)sulfonyl]-6-nitro-1H-indole
31271-89-3

N-[4-(methylphenyl)sulfonyl]-6-nitro-1H-indole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide99%
6-nitroindole
4769-96-4

6-nitroindole

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole
1247072-45-2

6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 16h; Inert atmosphere;
98.7%
Stage #1: 6-nitroindole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0℃; for 10h;
38%
6-nitroindole
4769-96-4

6-nitroindole

t-butyl 4-bromomethyl-3-methoxybenzoate
104436-91-1

t-butyl 4-bromomethyl-3-methoxybenzoate

tert-butyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate
104436-92-2

tert-butyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Heating;98%
6-nitroindole
4769-96-4

6-nitroindole

1-chloro 4-iodobutane
10297-05-9

1-chloro 4-iodobutane

1-(4-chlorobutyl)-6-nitro-1H-indole
915037-88-6

1-(4-chlorobutyl)-6-nitro-1H-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.0833333h;
Stage #2: 1-chloro 4-iodobutane In N,N-dimethyl-formamide at 20℃; for 0.5h;
97.6%
With sodium hydride In N,N-dimethyl-formamide
6-nitroindole
4769-96-4

6-nitroindole

ethyl bromoacetate
105-36-2

ethyl bromoacetate

(6-nitro-indol-1-yl)-acetic acid ethyl ester
915037-28-4

(6-nitro-indol-1-yl)-acetic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide for 0.416667h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 26h;
97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h;88%
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 0 - 25℃; Product distribution / selectivity;
57%
6-nitroindole
4769-96-4

6-nitroindole

1-methyl-6-nitro-indole
99459-48-0

1-methyl-6-nitro-indole

Conditions
ConditionsYield
With CH3I; NaH In dimethylformamide [DMF]; water97%
With potassium carbonate; methyl iodide In N,N-dimethyl-formamide
6-nitroindole
4769-96-4

6-nitroindole

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-((6-nitro-1H-indol-1-yl)methyl)benzoate

methyl 4-((6-nitro-1H-indol-1-yl)methyl)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux;97%
6-nitroindole
4769-96-4

6-nitroindole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-methyl-6-nitro-indole
99459-48-0

1-methyl-6-nitro-indole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 126℃; for 2h; Concentration; Reflux; Green chemistry;96%
With potassium carbonate In n-heptane; water; ethyl acetate; N,N-dimethyl-formamide96.1%
6-nitroindole
4769-96-4

6-nitroindole

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone
676476-90-7

2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone

Conditions
ConditionsYield
Stage #1: 6-nitroindole; trifluoroacetic anhydride In N,N-dimethyl-formamide at 60℃; for 3h;
Stage #2: With water; sodium hydrogencarbonate In ethyl acetate; N,N-dimethyl-formamide
96%
In tetrahydrofuran at 0 - 25℃; for 18h;40%
6-nitroindole
4769-96-4

6-nitroindole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

6-nitro-1-(phenylsulfonyl)-1H-indole
73282-17-4

6-nitro-1-(phenylsulfonyl)-1H-indole

Conditions
ConditionsYield
With potassium carbonate In acetone at 0 - 20℃; for 24h;96%
Stage #1: 6-nitroindole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere;
77%
6-nitroindole
4769-96-4

6-nitroindole

methyl 4-(bromomethyl)-3-methoxybenzoate
70264-94-7

methyl 4-(bromomethyl)-3-methoxybenzoate

methyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate
104437-17-4

methyl 3-methoxy-4-<(6-nitroindol-1-yl)methyl>benzoate

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Heating;95%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux;38%
With potassium carbonate In dichloromethane; ethyl acetate; acetone
6-nitroindole
4769-96-4

6-nitroindole

iodobenzene
591-50-4

iodobenzene

6-nitro-1-phenyl-1H-indole

6-nitro-1-phenyl-1H-indole

Conditions
ConditionsYield
With copper(l) iodide; metformin hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere;95%
6-nitroindole
4769-96-4

6-nitroindole

1-bromo-octane
111-83-1

1-bromo-octane

6-nitro-1-octyl-1H-indole

6-nitro-1-octyl-1H-indole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;95%
6-nitroindole
4769-96-4

6-nitroindole

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

3-(1-(4-methoxyphenyl)ethyl)-6-nitro-1H-indole

3-(1-(4-methoxyphenyl)ethyl)-6-nitro-1H-indole

Conditions
ConditionsYield
With 4,4'-sulfonediphenol In acetic acid butyl ester at 80℃; for 2h; Friedel-Crafts Alkylation; Sealed tube; Green chemistry;95%
ethyl bromide
74-96-4

ethyl bromide

6-nitroindole
4769-96-4

6-nitroindole

1-ethyl-6-nitro-1H-indole

1-ethyl-6-nitro-1H-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h;
Stage #2: ethyl bromide With sodium iodide In N,N-dimethyl-formamide; mineral oil
94.5%
6-nitroindole
4769-96-4

6-nitroindole

1-bromomethyl-3,5-difluoro-benzene
141776-91-2

1-bromomethyl-3,5-difluoro-benzene

1-(3,5-difluoro-benzyl)-6-nitro-1H-indole
691400-24-5

1-(3,5-difluoro-benzyl)-6-nitro-1H-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.25h;
Stage #2: 1-bromomethyl-3,5-difluoro-benzene In DMF (N,N-dimethyl-formamide)
94%
Stage #1: 6-nitroindole With 1-methyl-pyrrolidin-2-one; cesium carbonate at 0℃; for 0.5h;
Stage #2: 1-bromomethyl-3,5-difluoro-benzene at 20℃; for 18h;
Stage #1: 6-nitroindole With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.5h;
Stage #2: 1-bromomethyl-3,5-difluoro-benzene In DMF (N,N-dimethyl-formamide) for 1h;
6-nitroindole
4769-96-4

6-nitroindole

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

C16H10N2O4
1058165-03-9

C16H10N2O4

Conditions
ConditionsYield
In water at 80℃; for 24h; Friedel-Crafts reaction;93%
cyclopropyl trifluoromethyl ketone
75702-97-5

cyclopropyl trifluoromethyl ketone

6-nitroindole
4769-96-4

6-nitroindole

1-cyclopropyl-2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)ethanol

1-cyclopropyl-2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)ethanol

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 8h;93%
6-nitroindole
4769-96-4

6-nitroindole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

3,3'-((4-nitrophenyl)methylene)bis(6-nitro-1H-indole)

3,3'-((4-nitrophenyl)methylene)bis(6-nitro-1H-indole)

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate; sodium dodecyl-sulfate; silica gel In neat (no solvent) at 20℃; for 0.5h; Milling; Green chemistry;93%
6-nitroindole
4769-96-4

6-nitroindole

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

6-nitro-3-((trifluoromethyl)thio)-1H-indole

6-nitro-3-((trifluoromethyl)thio)-1H-indole

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;93%
6-nitroindole
4769-96-4

6-nitroindole

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

3-benzhydryl-6-nitro-1H-indole

3-benzhydryl-6-nitro-1H-indole

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II) In water at 120℃; for 16h; Sealed tube;92%
6-nitroindole
4769-96-4

6-nitroindole

L-serin
56-45-1

L-serin

6-nitro-L-tryptophan
46885-76-1

6-nitro-L-tryptophan

Conditions
ConditionsYield
With Pf0A9 E104G enzyme In aq. phosphate buffer; water; dimethyl sulfoxide at 75℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction;91%
6-nitroindole
4769-96-4

6-nitroindole

potassium thioacyanate
333-20-0

potassium thioacyanate

6-nitro-3-thiocyanato-1H-indole

6-nitro-3-thiocyanato-1H-indole

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; oxygen; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;91%
6-nitroindole
4769-96-4

6-nitroindole

4-bromomethyl-3-methoxybenzonitrile
104436-60-4

4-bromomethyl-3-methoxybenzonitrile

1-(4-cyano-2-methoxybenzyl)-6-nitroindole
104436-68-2

1-(4-cyano-2-methoxybenzyl)-6-nitroindole

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;90%
6-nitroindole
4769-96-4

6-nitroindole

1-iodo-3-chloro-propane
6940-76-7

1-iodo-3-chloro-propane

1-(3-chloropropyl)-6-nitro-1H-indole
915037-79-5

1-(3-chloropropyl)-6-nitro-1H-indole

Conditions
ConditionsYield
Stage #1: 6-nitroindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide at 20℃; for 3h;
90%
With sodium hydride In N,N-dimethyl-formamide

4769-96-4Relevant articles and documents

Two-Step Synthesis of Polysubstituted 6-Nitroindoles under Flow Chemical and Microwave Conditions

Sampaolesi, Susanna,Gabrielli, Serena,Ballini, Roberto,Palmieri, Alessandro

, p. 3407 - 3413 (2017)

A new simple and efficient synthesis of 6-nitroindoles, starting from N-carboxylalkylpyrrole-2-carboxaldehydes and protected β-nitro ketones, has been developed. The method involves two distinct domino processes, respectively performed under flow chemical conditions and microwave irradiation. 6-Nitroindoles were produced in good to excellent overall yields. (Figure presented.).

Monomeric vanadium oxide: A very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles

Xie, Zhenbing,Chen, Bingfeng,Zheng, Lirong,Peng, Fangfang,Liu, Huizhen,Han, Buxing

, p. 431 - 437 (2021/01/11)

Monomeric active species are very interesting in heterogeneous catalysis. In this work, we proposed a method to prepare VOx-NbOy@C catalysts, which involve the one-pot hydrothermal synthesis of inorganic/organic hybrid materials containing V/Nb followed by thermal treatment under a reducing atmosphere. The prepared catalysts were characterized using different techniques, such as high-angle annular dark-field scanning transmission electron microscopy and X-ray absorption fine structure spectroscopy. It was shown that monomeric VOx species were dispersed homogeneously in the catalysts. The VOx-NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study indicated that monomeric VO2 species were the most effective for promoting the reaction. This journal is

Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies

Luo, Zaoli,Liu, Yungen,Tong, Ka-Chung,Chang, Xiao-Yong,To, Wai-Pong,Che, Chi-Ming

, p. 2978 - 2992 (2021/08/30)

A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallographic analyses. The electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima from 566 nm to 706 nm, with two of them having emission quantum yields >60% and lifetimes 2 μs in solutions at room temperature, whereas the platinum(II) diacetylide complexes having bis-N-heterocyclic carbene instead of diimine ligand display photoluminescence with quantum yields of up to 28% in solutions and excited state lifetimes of up to 62 μs at room temperature. Application studies revealed that one of the complexes can catalyze photoinduced aerobic dehydrogenation of alcohols and alkenes, and a relatively non-toxic water-soluble Pt(II) complex displays anti-angiogenic activity.

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya

supporting information, p. 5240 - 5245 (2020/07/03)

The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.

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