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10075-50-0

Basic Information
CAS No.: 10075-50-0
Name: 5-Bromoindole
Molecular Structure:
Molecular Structure of 10075-50-0 (5-Bromoindole)
Formula: C8H6BrN
Molecular Weight: 196.05
Synonyms: 1H-Indole, 5-bromo- (9CI);5-bromo-1H-indole;1H-Indole, 5-bromo-;5-Bromo Indole;
EINECS: 233-208-7
Density: 1.66 g/cm3
Melting Point: 89-92 °C
Boiling Point: 316.9 °C at 760 mmHg
Flash Point: 145.5 °C
Solubility:
Appearance: white to light brown powder or chunks
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25-37/39
Transport Information:
PSA: 15.79000
LogP: 2.93040
Synthetic route
1196980-99-0

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

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%
10406-06-1

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

10075-50-0

5-bromo-1H-indole

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

5-bromoindoline

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%
118757-11-2

1-Benzenesulfonyl-5-bromo-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%
182344-70-3

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

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.
96546-77-9

N-tosyl-5-bromoindole

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;
26807-69-2

N-acetylindololine-2-sulfonic acid sodium

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%
128373-13-7

1H-indol-5-yl trifluoromethanesulfonate

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%
88131-63-9

5-Bromo-1-(methylsulfonyl)indole

10075-50-0

5-bromo-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In methanol for 18h; Heating;85%

5-bromoindoline-2-carboxylic acid

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%
127-17-3

2-oxo-propionic acid

589-21-9

(4-bromophenyl)hydrazine

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

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%
918529-91-6

5-bromo-1-carbomethoxyindoline

A

10075-50-0

5-bromo-1H-indole

B

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

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

A

10075-50-0

5-bromo-1H-indole

B

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%
877-03-2

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

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%
120-72-9

indole

1147550-11-5

ammonium thiocyanate

A

10075-50-0

5-bromo-1H-indole

B

23706-25-4

3-thiocyanatoindole

Conditions
ConditionsYield
With N-BromosuccinimideA n/a
B 60%
125914-22-9

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

10075-50-0

5-bromo-1H-indole

Conditions
ConditionsYield
With hydrogen In para-xylene at 25℃; under 760.051 Torr; for 24h; Solvent;60%
10075-50-0

5-bromo-1H-indole

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; tryptophanase TnaA at 25℃; pH=7.4; Enzymatic reaction;60%
125914-22-9

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

A

10075-50-0

5-bromo-1H-indole

B

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%
105896-41-1

N-(4-bromophenyl)ethenesulfinamide

10075-50-0

5-bromo-1H-indole

Conditions
ConditionsYield
In toluene at 110℃; for 1h;49%
105205-48-9

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

10075-50-0

5-bromo-1H-indole

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

5-bromo-2-nitrobenzaldehyde

86302-43-4

(tert-Butoxycarbonylmethylene)triphenylphosphorane

10075-50-0

5-bromo-1H-indole

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

vinyl magnesium bromide

586-78-7

para-nitrophenyl bromide

A

10075-50-0

5-bromo-1H-indole

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
In tetrahydrofuran at -40℃;A 12%
B 42%
125914-22-9

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

A

120-72-9

indole

B

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%
7254-19-5

5-bromo-2-indolecarboxylic acid

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
10075-50-0

5-Bromoindolyl radical cation

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;
112671-53-1

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

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

10075-50-0

5-bromo-1H-indole

Conditions
ConditionsYield
With glycerol
10075-50-0

5-bromo-1H-indole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

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%
10075-50-0

5-bromo-1H-indole

98-59-9

p-toluenesulfonyl chloride

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%
10075-50-0

5-bromo-1H-indole

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

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

5-bromo-1H-indole

74-88-4

methyl iodide

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%
10075-50-0

5-bromo-1H-indole

24424-99-5

di-tert-butyl dicarbonate

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%
10075-50-0

5-bromo-1H-indole

105-36-2

ethyl bromoacetate

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%
10075-50-0

5-bromo-1H-indole

13154-24-0

triisopropylsilyl chloride

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%
10075-50-0

5-bromo-1H-indole

78-94-4

methyl vinyl ketone

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%
10075-50-0

5-bromo-1H-indole

100-52-7

benzaldehyde

phenyl(indol-5-yl)methanol

Conditions
ConditionsYield
With lithium dibutyl(isopropyl)magnesate In tetrahydrofuran100%
10075-50-0

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%
5683-33-0

2-(Dimethylamino)pyridine

10075-50-0

5-bromo-1H-indole

dibutyldicarbonate

dibutyldicarbonate

bromoindolecarboxylic Acid T-Butyl Ester

Conditions
ConditionsYield
In dichloromethane100%
10075-50-0

5-bromo-1H-indole

1069135-01-8

methyl 2-(diallylamino)-2-methoxyacetate

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%
10075-50-0

5-bromo-1H-indole

100-53-8

phenylmethanethiol

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%
10075-50-0

5-bromo-1H-indole

111-83-1

1-bromo-octane

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;
446-48-0

o-fluorobenzyl bromide

10075-50-0

5-bromo-1H-indole

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%
10075-50-0

5-bromo-1H-indole

76-02-8

Trichloroacetyl chloride

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;
10075-50-0

5-bromo-1H-indole

74-83-9

methyl bromide

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%
10075-50-0

5-bromo-1H-indole

13081-18-0

ethyl-3,3,3-trifluoropyruvate

(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;
10075-50-0

5-bromo-1H-indole

5153-67-3

nitrostyrene

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%
10075-50-0

5-bromo-1H-indole

100-52-7

benzaldehyde

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%
10075-50-0

5-bromo-1H-indole

100-39-0

benzyl bromide

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%
10075-50-0

5-bromo-1H-indole

16419-60-6

2-Methylphenylboronic acid

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.
10075-50-0

5-bromo-1H-indole

1147550-11-5

ammonium thiocyanate

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%
109-01-3

1-methyl-piperazine

10075-50-0

5-bromo-1H-indole

201230-82-2

carbon monoxide

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%
10075-50-0

5-bromo-1H-indole

2759-28-6

1-phenylmethylpiperazine

201230-82-2

carbon monoxide

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%
10075-50-0

5-bromo-1H-indole

927-74-2

1-butyn-4-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%
10075-50-0

5-bromo-1H-indole

555-16-8

4-nitrobenzaldehdye

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%
10075-50-0

5-bromo-1H-indole

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%
10075-50-0

5-bromo-1H-indole

98-09-9

benzenesulfonyl chloride

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%
10075-50-0

5-bromo-1H-indole

106-96-7

propargyl bromide

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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    Name 5-Bromoindole Synonyms 5-Bromo-1H-indole Molecular Structure Molecular Formula C8H6Br

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    5-Bromoindole

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  • 5-Bromoindole            10075-50-0

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Specification

The IUPAC name of 5-Bromoindole. With the CAS registry number 10075-50-0, it is also named as 1H-Indole, 5-bromo- ; 5-Bromo-1H-indole . The product's categories are blocks, bromides, indole/indoline/oxindole, indoles and derivatives, halides, organohalides, simple indoles and heterocyclic building blocks.The 5-Bromoindole is white to light brown powder or chunks which should be stored at the temperature of -20°C. It is used as pharmaceutical intermediates.5-Bromoindole is Irritating to eyes, respiratory system and skin.So when you use it ,you should avoid contact with skin and eyes  and wear suitable protective clothing, gloves and eye/face protection .In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .

Uses of 5-Bromoindole:
It  also can be used in the preparation of other chemicals. Foe example: 1. It can react with 3-bromo-2-hydroxyimino-propionic acid ethyl ester to get ethyl 2-hydroximino-3-(5-bromoindol-3-yl)propanoate .

It also reacts with dichloroacetyl chloride to obtain N-{4-bromo-2-[6-bromo-3-(5-bromo-1H-indol-3-yl)-quinolin-2-ylmethyl]-phenyl}-2,2-dichloro-acetamide .

This product is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

The other characteristics of 5-Bromoindole can be summarized as: 
(1)ACD/LogP:  2.788; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  2.79; (4)ACD/LogD (pH 7.4):  2.79; (5)ACD/BCF (pH 5.5):  77.38; (6)ACD/BCF (pH 7.4):  77.38; (7)ACD/KOC (pH 5.5):  782.50; (8)ACD/KOC (pH 7.4):  782.50; (9)#H bond acceptors:  1; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.711; (13)Molar Refractivity:  46.219 cm3; (14)Molar Volume:  118.056 cm3; (15)Polarizability:  18.323 10-24cm3 ; (16)Surface Tension:  54.8009986877441 dyne/cm; (17)Density:  1.661 g/cm3; (18)Flash Point:  145.484 °C; (19)Enthalpy of Vaporization:  53.608 kJ/mol; (20)Boiling Point:  316.946 °C at 760 mmHg; (21)Vapour Pressure:  0.00100000004749745 mmHg at 25°C.

People can use the following data to convert to the molecule structure:
(1)SMILES:Brc1cc2c(cc1)ncc2;
(2)Std. InChI:InChI=1S/C8H6BrN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H;
(3)Std. InChIKey:VXWVFZFZYXOBTA-UHFFFAOYSA-N.

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