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5-Bromoindole
Cas No: 10075-50-0
No Data 1 Gram 100 Kilogram/Month HANGZHOU YUNUO CHEMICAL CO.,LTD Contact Supplier
5-Bromoindole 10075-50-0 Factory PRICE IN STOCK COA CAS 10075-50-0
Cas No: 10075-50-0
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Cas No: 10075-50-0
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality 5-Bromoindole supplier in China
Cas No: 10075-50-0
No Data 1 Metric Ton 30 Metric Ton/Month Simagchem Corporation Contact Supplier
High purity 10075-50-0 5-Bromoindole
Cas No: 10075-50-0
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
5-Bromoindole
Cas No: 10075-50-0
USD $ 2.0-2.0 / Gram 100 Gram 100 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
10075-50-0 5-bromoindole
Cas No: 10075-50-0
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
5-Bromoindole
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No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
5-Bromoindole
Cas No: 10075-50-0
USD $ 5.0-5.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
5-Bromoindole CAS: 10075-50-0
Cas No: 10075-50-0
USD $ 1.0-2.0 / Metric Ton 5 Metric Ton 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier

10075-50-0 Usage

Purification Methods

Purify it by steam distillation from a faintly alkaline solution. Cool the aqueous distillate, collect the solid, dry it in a vacuum desiccator over P2O5 and recrystallise it from aqueous EtOH (35% EtOH) or pet ether/Et2O. UV in MeOH has at 279, 287 and 296nm (log 3.70, 3.69 and 3.53). The picrate has m 137-138o(dec) (from max Et2O/pet ether). [UV: Thesing et al. Chem Ber 95 2205 1962, UV and NMR: Lallemand & Bernath Bull Soc Chim Fr 4091 1970, Beilstein 20/7 V 36.]

Chemical Properties

white to light brown powder or chunks

Uses

A potential inhibitor of GSK-3
InChI:InChI=1/C8H6BrN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

10075-50-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (B68607)  5-Bromoindole  99% 10075-50-0 B68607-25G 852.93CNY Detail
Aldrich (B68607)  5-Bromoindole  99% 10075-50-0 B68607-5G 177.84CNY Detail
Alfa Aesar (B20307)  5-Bromoindole, 99%    10075-50-0 100g 3688.0CNY Detail
Alfa Aesar (B20307)  5-Bromoindole, 99%    10075-50-0 25g 1101.0CNY Detail
Alfa Aesar (B20307)  5-Bromoindole, 99%    10075-50-0 5g 240.0CNY Detail

10075-50-0SDS

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-Bromoindole

1.2 Other means of identification

Product number -
Other names 5-Br-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:10075-50-0 SDS

10075-50-0Synthetic route

1-(5-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one
1196980-99-0

1-(5-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one

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

5-bromo-1H-indole

Conditions
ConditionsYield
With water; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;99%
5-bromo-1H-indole-3-carboxylic acid
10406-06-1

5-bromo-1H-indole-3-carboxylic acid

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

5-bromo-1H-indole

Conditions
ConditionsYield
With potassium carbonate In ethanol at 140℃; Schlenk technique;99%
5-bromoindoline
22190-33-6

5-bromoindoline

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

5-bromo-1H-indole

Conditions
ConditionsYield
With potassium tert-butylate In decane at 150℃; for 36h; Inert atmosphere; Schlenk technique;98%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In para-xylene at 130℃; for 20h; Inert atmosphere; Sealed tube;98%
With 6C44H32N6O4Ru(2+)*12Hf(2+)*8O(2-)*14HO(1-)*6C16H22ClCoN5O6(1-) In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Irradiation;98%
1-Benzenesulfonyl-5-bromo-indole
118757-11-2

1-Benzenesulfonyl-5-bromo-indole

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

5-bromo-1H-indole

Conditions
ConditionsYield
With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;94%
5-bromo-indole-1-carboxylic acid tert-butyl ester
182344-70-3

5-bromo-indole-1-carboxylic acid tert-butyl ester

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

5-bromo-1H-indole

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 0.5h;92%
With potassium carbonate In methanol; water for 3h; Heating;87%
With potassium hydroxide In toluene at 150℃; for 0.5h; microwave irradiation;80%
With Verkade's base (R=i-Bu) In methanol at 20℃; for 19h;97 % Chromat.
N-tosyl-5-bromoindole
96546-77-9

N-tosyl-5-bromoindole

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

5-bromo-1H-indole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 1h; Inert atmosphere;92%
With caesium carbonate In tetrahydrofuran; methanol at 22℃; for 15h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; reagent ratios;88.2%
With cetyltrimethylammonim bromide; potassium hydroxide In tetrahydrofuran; water for 26h; Reflux; Green chemistry;
N-acetylindololine-2-sulfonic acid sodium
26807-69-2

N-acetylindololine-2-sulfonic acid sodium

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

5-bromo-1H-indole

Conditions
ConditionsYield
Stage #1: N-acetylindololine-2-sulfonic acid sodium With bromine In water at 0 - 20℃; for 2h;
Stage #2: With sodium hydroxide In water for 20h; Reflux;
92%
Stage #1: N-acetylindololine-2-sulfonic acid sodium With bromine In water at 0 - 20℃;
Stage #2: With sodium hydroxide In water for 20h; Reflux;
92%
With bromine In water at 0 - 5℃; for 0.5h;88%
1H-indol-5-yl trifluoromethanesulfonate
128373-13-7

1H-indol-5-yl trifluoromethanesulfonate

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

5-bromo-1H-indole

Conditions
ConditionsYield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 120℃; for 24h; Inert atmosphere;88%
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;75%
5-Bromo-1-(methylsulfonyl)indole
88131-63-9

5-Bromo-1-(methylsulfonyl)indole

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

5-bromo-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In methanol for 18h; Heating;85%
5-bromoindoline-2-carboxylic acid

5-bromoindoline-2-carboxylic acid

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

5-bromo-1H-indole

Conditions
ConditionsYield
With 2C16H35N*I4Pb(2-)*2H(1+); oxygen In dichloromethane for 14h; Inert atmosphere; Sealed tube; Irradiation;84%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(4-bromophenyl)hydrazine
589-21-9

(4-bromophenyl)hydrazine

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

5-bromo-1H-indole

Conditions
ConditionsYield
With phosphorus pentachloride; zinc(II) chloride for 0.0666667h; microwave irradiation;83%
1-allyl-5-bromo-1H-indole

1-allyl-5-bromo-1H-indole

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

5-bromo-1H-indole

Conditions
ConditionsYield
Grubbs catalyst first generation In toluene for 5h; Heating;81%
Grubbs catalyst first generation In toluene at 110℃; for 5h;81%
5-bromo-1-carbomethoxyindoline
918529-91-6

5-bromo-1-carbomethoxyindoline

A

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

5-bromo-1H-indole

B

3,5-dibromo-1H-indole
81387-89-5

3,5-dibromo-1H-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1-carbomethoxyindoline With bromine In tetrachloromethane for 2h;
Stage #2: With sodium hydride In methanol for 2h; Heating; Further stages.;
A 75%
B 5%
sodium 1-acetyl-1H-indole-2-sulfonate

sodium 1-acetyl-1H-indole-2-sulfonate

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

5-bromo-1H-indole

Conditions
ConditionsYield
With water; bromine at 0 - 20℃; for 2h;74%
Stage #1: sodium 1-acetyl-1H-indole-2-sulfonate With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 60 - 80℃; for 8h; pH=10; Concentration; Temperature;
sodium 1-acetyl-1H-indole-2-sulfonate

sodium 1-acetyl-1H-indole-2-sulfonate

A

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

5-bromo-1H-indole

B

5,7-dibromo-1H-indole
36132-08-8

5,7-dibromo-1H-indole

Conditions
ConditionsYield
Stage #1: sodium 1-acetyl-1H-indole-2-sulfonate With bromine In water at 0 - 20℃; for 2h;
Stage #2: With sodium hydrogensulfite; sodium hydroxide In water for 20h; Reflux;
A 70.9%
B 11.9%
5-bromo-1H-indole-3-carboxaldehyde
877-03-2

5-bromo-1H-indole-3-carboxaldehyde

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

5-bromo-1H-indole

Conditions
ConditionsYield
With perchloric acid adsorbed on silica gel; anthranilic acid amide In acetonitrile at 80℃; for 6h;65%
indole
120-72-9

indole

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

A

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

5-bromo-1H-indole

B

3-thiocyanatoindole
23706-25-4

3-thiocyanatoindole

Conditions
ConditionsYield
With N-BromosuccinimideA n/a
B 60%
2-(5-bromo-2-nitrophenyl)acetonitrile
125914-22-9

2-(5-bromo-2-nitrophenyl)acetonitrile

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

5-bromo-1H-indole

Conditions
ConditionsYield
With hydrogen In para-xylene at 25℃; under 760.051 Torr; for 24h; Solvent;60%
5-bromo-DL-tryptophan
6548-09-0, 25197-99-3, 93299-40-2

5-bromo-DL-tryptophan

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

5-bromo-1H-indole

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; tryptophanase TnaA at 25℃; pH=7.4; Enzymatic reaction;60%
2-(5-bromo-2-nitrophenyl)acetonitrile
125914-22-9

2-(5-bromo-2-nitrophenyl)acetonitrile

A

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

5-bromo-1H-indole

B

2-(2-amino-5-bromophenyl)acetonitrile
882855-95-0

2-(2-amino-5-bromophenyl)acetonitrile

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; under 760.051 Torr; for 24h; Solvent;A 10%
B 52%
N-(4-bromophenyl)ethenesulfinamide
105896-41-1

N-(4-bromophenyl)ethenesulfinamide

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

5-bromo-1H-indole

Conditions
ConditionsYield
In toluene at 110℃; for 1h;49%
[(E)-2-(5-bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine
105205-48-9

[(E)-2-(5-bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine

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

5-bromo-1H-indole

Conditions
ConditionsYield
With zinc In acetic acid at 85℃; for 2h;47%
5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

(tert-Butoxycarbonylmethylene)triphenylphosphorane
86302-43-4

(tert-Butoxycarbonylmethylene)triphenylphosphorane

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

5-bromo-1H-indole

Conditions
ConditionsYield
With triphenylphosphine In diphenylether at 260℃; for 1h;46%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

A

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

5-bromo-1H-indole

B

4-bromo-aniline
106-40-1

4-bromo-aniline

Conditions
ConditionsYield
In tetrahydrofuran at -40℃;A 12%
B 42%
2-(5-bromo-2-nitrophenyl)acetonitrile
125914-22-9

2-(5-bromo-2-nitrophenyl)acetonitrile

A

indole
120-72-9

indole

B

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

5-bromo-1H-indole

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; under 760.051 Torr; for 24h; Solvent;A 36%
B 34%
5-bromo-2-indolecarboxylic acid
7254-19-5

5-bromo-2-indolecarboxylic acid

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

5-bromo-1H-indole

Conditions
ConditionsYield
With quinoline; copper(I) bromide
With copper oxide-chromium oxide; copper
With quinoline; copper oxide-chromium oxide
5-Bromoindolyl radical cation
10075-50-0

5-Bromoindolyl radical cation

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

5-bromo-1H-indole

Conditions
ConditionsYield
With 10-[2-(dimethylamino)propyl]phenothiazine In water at 20℃; Rate constant; Equilibrium constant; pH 6.5;
(4-Bromo-2-trimethylsilanylethynyl-phenyl)-carbamic acid ethyl ester
112671-53-1

(4-Bromo-2-trimethylsilanylethynyl-phenyl)-carbamic acid ethyl ester

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

5-bromo-1H-indole

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating; Yield given;
ammonium salt of/the/ 5-bromo-indole-2-carboxylic acid

ammonium salt of/the/ 5-bromo-indole-2-carboxylic acid

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

5-bromo-1H-indole

Conditions
ConditionsYield
With glycerol
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

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

N,N-dimethyl-formamide

5-bromo-1H-indole-3-carboxaldehyde
877-03-2

5-bromo-1H-indole-3-carboxaldehyde

Conditions
ConditionsYield
With trichlorophosphate100%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate Cooling with ice;
Stage #2: 5-bromo-1H-indole In N,N-dimethyl-formamide at 20℃; Cooling with ice;
Stage #3: With water; potassium hydroxide In N,N-dimethyl-formamide Reflux;
100%
With trichlorophosphate In DMF (N,N-dimethyl-formamide) at 0 - 40℃; for 2.25h; Vilsmeier Formylation;100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-tosyl-5-bromoindole
96546-77-9

N-tosyl-5-bromoindole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 20℃; for 4.5h;
100%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 20℃;99%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 20℃;99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

1-(5-Bromo-1H-indol-3-yl)-4,5-dichloro-3-hydroxy-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

1-(5-Bromo-1H-indol-3-yl)-4,5-dichloro-3-hydroxy-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions
ConditionsYield
In 1,4-dioxane for 120h; Ambient temperature;100%
In 1,4-dioxane at 20℃; for 0.5h;
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

methyl iodide
74-88-4

methyl iodide

5-bromo-1-methyl-H-indole
10075-52-2

5-bromo-1-methyl-H-indole

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran100%
With sodium hydride In dimethyl sulfoxide99%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
98%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-bromo-indole-1-carboxylic acid tert-butyl ester
182344-70-3

5-bromo-indole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
dmap In acetonitrile at 20℃; for 3h;100%
With dmap In acetonitrile at 23℃; for 0.5h; Inert atmosphere;99%
With dmap In acetonitrile at 23℃; for 0.5h;99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 2-(5-bromo-1H-indol-1-yl)acetate
726174-45-4

ethyl 2-(5-bromo-1H-indol-1-yl)acetate

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃;
100%
Stage #1: 5-bromo-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: ethyl bromoacetate In tetrahydrofuran at 20℃;
47.7%
Stage #1: 5-bromo-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: ethyl bromoacetate In tetrahydrofuran at 20℃; for 1h;
42%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

5-bromo-1-triisopropylsilyl-1H-indole
128564-66-9

5-bromo-1-triisopropylsilyl-1H-indole

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Inert atmosphere;100%
Stage #1: 5-bromo-1H-indole With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: triisopropylsilyl chloride In tetrahydrofuran at -78 - 20℃; for 1.33333h;
99%
Stage #1: 5-bromo-1H-indole With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: triisopropylsilyl chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

methyl vinyl ketone
78-94-4

methyl vinyl ketone

4-(5-bromo-1H-3-indolyl)-2-butanone

4-(5-bromo-1H-3-indolyl)-2-butanone

Conditions
ConditionsYield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.116667h; Michael addition;100%
With phosphotungstic acid In water at 20℃; for 1h; Michael addition;97%
sodium tetrachloroaurate dihydrate In various solvent(s) at 80℃; for 24h;95%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

benzaldehyde
100-52-7

benzaldehyde

phenyl(indol-5-yl)methanol

phenyl(indol-5-yl)methanol

Conditions
ConditionsYield
With lithium dibutyl(isopropyl)magnesate In tetrahydrofuran100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

3-iodo-5-bromo-1H-indole

3-iodo-5-bromo-1H-indole

Conditions
ConditionsYield
With iodine; potassium iodide; sodium hydroxide In methanol; water at 20℃; for 3h;100%
With iodine; potassium iodide; sodium hydroxide In methanol; water at 20℃; for 3h; Darkness;100%
With N-iodo-succinimide In dimethyl sulfoxide at 30℃; for 0.5h;93%
2-(Dimethylamino)pyridine
5683-33-0

2-(Dimethylamino)pyridine

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

5-bromo-1H-indole

dibutyldicarbonate

dibutyldicarbonate

bromoindolecarboxylic Acid T-Butyl Ester

bromoindolecarboxylic Acid T-Butyl Ester

Conditions
ConditionsYield
In dichloromethane100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

methyl 2-(diallylamino)-2-methoxyacetate
1069135-01-8

methyl 2-(diallylamino)-2-methoxyacetate

methyl 2-(5-bromo-1H-indol-3-yl)-2-(diallylamino)acetate
1069135-03-0

methyl 2-(5-bromo-1H-indol-3-yl)-2-(diallylamino)acetate

Conditions
ConditionsYield
With hafnium tetrakis(trifluoromethanesulfonate); chloro-trimethyl-silane In dichloromethane at 20℃; for 1h;100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

phenylmethanethiol
100-53-8

phenylmethanethiol

5-(benzylthio)-1H-indole
92554-49-9

5-(benzylthio)-1H-indole

Conditions
ConditionsYield
Stage #1: phenylmethanethiol With sodium t-butanolate In tetrahydrofuran at 23℃; for 0.166667h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.166667h; Inert atmosphere;
Stage #3: 5-bromo-1H-indole With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); lithium iodide In tetrahydrofuran at 90℃; for 2h; Inert atmosphere;
100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1-bromo-octane
111-83-1

1-bromo-octane

5-bromo-1-octyl-1H-indole
1244769-53-6

5-bromo-1-octyl-1H-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 1h;
Stage #2: 1-bromo-octane In dimethyl sulfoxide; mineral oil at 20℃; for 3h;
100%
Stage #1: 5-bromo-1H-indole With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 1h;
Stage #2: 1-bromo-octane In dimethyl sulfoxide; mineral oil at 20℃; for 3h;
92%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h;
Stage #2: 1-bromo-octane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
90%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h;
Stage #2: 1-bromo-octane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
80%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil
Stage #2: 1-bromo-octane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h;
o-fluorobenzyl bromide
446-48-0

o-fluorobenzyl bromide

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

5-bromo-1H-indole

N-2-Fluorobenzyl-5-bromoindole
676581-33-2

N-2-Fluorobenzyl-5-bromoindole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide for 0.5h;
Stage #2: o-fluorobenzyl bromide In N,N-dimethyl-formamide at 50℃; for 5h;
100%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

2,2,2-trichloro-1-(5-bromo-1H-indol-3-yl)ethan-1-one

2,2,2-trichloro-1-(5-bromo-1H-indol-3-yl)ethan-1-one

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
Stage #1: 5-bromo-1H-indole With pyridine In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: trifluoroacetyl chloride In tetrahydrofuran at 20℃; for 16h;
With pyridine; dmap In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

methyl bromide
74-83-9

methyl bromide

5-bromo-1-methyl-H-indole
10075-52-2

5-bromo-1-methyl-H-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: methyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
100%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: methyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
100%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: methyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
81%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-bromoindol-3-yl)propionic acid ethyl ester

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-bromoindol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;99.1%
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-bromo-1H-indole In toluene at -78℃; for 17h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
96%
With cinchonidine In diethyl ether at -8℃;
With cinchonidine In diethyl ether at -8℃; for 3h; enantioselective reaction;
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

nitrostyrene
5153-67-3

nitrostyrene

5-bromo-3-(2-nitro-1-phenylethyl)-1H-indole

5-bromo-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions
ConditionsYield
Stage #1: nitrostyrene With (S)-10,10'-bis[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-9,9'-biphenanthrene; zinc(II) trifluoroacetate In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: 5-bromo-1H-indole In diethyl ether at 20℃; Friedel-Crafts alkylation; Inert atmosphere;
99%
With magnesium iodide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;94%
With tetrabutylammomium bromide In acetonitrile for 0.166667h; Michael addition reaction; Heating;90%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

benzaldehyde
100-52-7

benzaldehyde

3,3'-(phenylmethylene)bis-(5-bromo-1H-indole)

3,3'-(phenylmethylene)bis-(5-bromo-1H-indole)

Conditions
ConditionsYield
With Amberlyst sulfonic acid form In acetonitrile at 20℃; for 5h;99%
With pyridinium hydrobromide perbromide In ethyl acetate at 20℃; for 0.25h;99%
With Montmorillonite K10 clay at 20℃; for 0.0833333h;96%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-5-bromo-1H-indole
10075-51-1

1-benzyl-5-bromo-1H-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: benzyl bromide In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; Schlenk technique;
99%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
99%
Stage #1: 5-bromo-1H-indole With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;
93%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

5-(2-methylphenyl)-1H-indole

5-(2-methylphenyl)-1H-indole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 5h; Suzuki coupling; Heating;99%
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction;70%
With potassium carbonate In toluene at 90℃; for 1h; Suzuki coupling; Inert atmosphere;35 %Chromat.
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

5-bromo-3-thiocyanatoindole

5-bromo-3-thiocyanatoindole

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;99%
With ammonium cerium (IV) nitrate In methanol at 25℃; for 0.25h;97%
With iodine pentoxide In methanol at 20℃; for 0.33h;96%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

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

5-bromo-1H-indole

carbon monoxide
201230-82-2

carbon monoxide

(1H-indol-5-yl)(4-methylpiperazin-1-yl)methanone
640734-92-5

(1H-indol-5-yl)(4-methylpiperazin-1-yl)methanone

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride; triethylamine In toluene at 130℃; under 18751.5 Torr; for 20h;99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1-phenylmethylpiperazine
2759-28-6

1-phenylmethylpiperazine

carbon monoxide
201230-82-2

carbon monoxide

N-benzyl-N'-(5-indolylcarbonyl)piperazine

N-benzyl-N'-(5-indolylcarbonyl)piperazine

Conditions
ConditionsYield
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride In toluene at 130℃; under 18751.9 Torr; for 20h;99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

1-butyn-4-ol
927-74-2

1-butyn-4-ol

4-(Indol-5-yl)-3-butyn-1-ol

4-(Indol-5-yl)-3-butyn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 100℃; for 20h;99%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

5-bromo-3-((5-bromo-1H-indol-3-yl)(4-nitrophenyl)methyl)-1H-indole

5-bromo-3-((5-bromo-1H-indol-3-yl)(4-nitrophenyl)methyl)-1H-indole

Conditions
ConditionsYield
With Amberlyst sulfonic acid form In acetonitrile at 20℃; for 4h;99%
With 1,1,3,3-tetramethylguanidinium chlorosulfonate In neat (no solvent) at 20℃; Green chemistry;96%
With 1,1,3,3-tetramethylguanidinium chlorosulfonate In neat (no solvent) at 20℃; for 0.2h;96%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

5-bromoindoline
22190-33-6

5-bromoindoline

Conditions
ConditionsYield
With potassium tert-butylate; hydrogen; C31H31BrMnNO2P2 In toluene at 100℃; under 37503.8 Torr; for 36h; Autoclave; chemoselective reaction;99%
With C30H29BrMnNO2P2; hydrogen; caesium carbonate In toluene at 100℃; under 37503.8 Torr; for 36h; Autoclave;99%
With sodium cyanoborohydride In acetic acid at 20℃; Inert atmosphere;93%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-Benzenesulfonyl-5-bromo-indole
118757-11-2

1-Benzenesulfonyl-5-bromo-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 50℃;
99%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 0℃; for 3h;95%
Stage #1: 5-bromo-1H-indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.166667h;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil for 2h;
95%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

propargyl bromide
106-96-7

propargyl bromide

5-bromo-1-(prop-2-yn-1-yl)-1H-indole

5-bromo-1-(prop-2-yn-1-yl)-1H-indole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: propargyl bromide In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; Schlenk technique;
99%
With sodium hydroxide; tetrabutylammomium bromide In water; toluene at 20℃; for 3h;93%
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃;
77%

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