10075-50-0

Basic information

• Product Name: 5-Bromoindole
• Synonyms: 5-BROMOBENZOTHOAZOLE;5-BROMOINDAN-1-ONE;5-BROMO INDOLE pure;1H-Indole, 5-bromo-;5-broMo-2H-indole;5-BroMoindole, 99% 5GR;5-BroMoindole (KSM-II);5-broMinatedindole
• CAS NO: 10075-50-0
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.04
• EINECS: 233-208-7
• Product Categories: IndolesOxindoles;Indole/indoline/oxindole;Indoles and derivatives;IndoleDerivative;Halides;Pyrroles & Indoles;Indole;Indoles;Organohalides;Simple Indoles;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks;Pharmaceutical Intermediates;Indole Derivatives;Heterocycle-Indole series;blocks;Bromides
• Mol File: 10075-50-0.mol
• Article Data: 91

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 228.5°C (rough estimate)
• Flash Point: 145.5 °C
• Appearance: White to light brown/Powder or Chunks
• Density: 1.5466 (rough estimate)
• Vapor Pressure: 0.000738mmHg at 25°C
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: -20°C
• Solubility: 126mg/l (calculated)
• PKA: 16.04±0.30(Predicted)
• BRN: 112877
• CAS DataBase Reference: 5-Bromoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoindole(10075-50-0)
• EPA Substance Registry System: 5-Bromoindole(10075-50-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39
• WGK Germany: 3
• Hazardous Substances Data: 10075-50-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light brown powder or chunks

Uses

A potential inhibitor of GSK-3

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

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.]

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

Synthetic route

1-(5-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one (1196980-99-0) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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 (10075-50-0)

Conditions	Yield
With potassium carbonate In ethanol at 140℃; Schlenk technique;	99%

5-bromoindoline (22190-33-6) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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-1H-indole (10075-50-0)

Conditions	Yield
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) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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-1H-indole (10075-50-0)

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

5-bromoindoline-2-carboxylic acid → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With 2C16H35N*I4Pb(2-)*2H(1+); oxygen In dichloromethane for 14h; Inert atmosphere; Sealed tube; Irradiation;	84%

2-oxo-propionic acid (127-17-3) + (4-bromophenyl)hydrazine (589-21-9) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With phosphorus pentachloride; zinc(II) chloride for 0.0666667h; microwave irradiation;	83%

1-allyl-5-bromo-1H-indole → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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-1H-indole (10075-50-0) + 3,5-dibromo-1H-indole (81387-89-5)

Conditions	Yield
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 → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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 → 5-bromo-1H-indole (10075-50-0) + 5,7-dibromo-1H-indole (36132-08-8)

Conditions	Yield
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 (10075-50-0)

Conditions	Yield
With perchloric acid adsorbed on silica gel; anthranilic acid amide In acetonitrile at 80℃; for 6h;	65%

indole (120-72-9) + ammonium thiocyanate (1147550-11-5) → 5-bromo-1H-indole (10075-50-0) + 3-thiocyanatoindole (23706-25-4)

Conditions	Yield
With N-Bromosuccinimide	A n/a B 60%

2-(5-bromo-2-nitrophenyl)acetonitrile (125914-22-9) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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-1H-indole (10075-50-0)

Conditions	Yield
With dipotassium hydrogenphosphate; tryptophanase TnaA at 25℃; pH=7.4; Enzymatic reaction;	60%

2-(5-bromo-2-nitrophenyl)acetonitrile (125914-22-9) → 5-bromo-1H-indole (10075-50-0) + 2-(2-amino-5-bromophenyl)acetonitrile (882855-95-0)

Conditions	Yield
With hydrogen In methanol at 25℃; under 760.051 Torr; for 24h; Solvent;	A 10% B 52%

N-(4-bromophenyl)ethenesulfinamide (105896-41-1) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
In toluene at 110℃; for 1h;	49%

[(E)-2-(5-bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine (105205-48-9) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With zinc In acetic acid at 85℃; for 2h;	47%

5-bromo-2-nitrobenzaldehyde (20357-20-4) + (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With triphenylphosphine In diphenylether at 260℃; for 1h;	46%

vinyl magnesium bromide (1826-67-1) + para-nitrophenyl bromide (586-78-7) → 5-bromo-1H-indole (10075-50-0) + 4-bromo-aniline (106-40-1)

Conditions	Yield
In tetrahydrofuran at -40℃;	A 12% B 42%

2-(5-bromo-2-nitrophenyl)acetonitrile (125914-22-9) → indole (120-72-9) + 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
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-1H-indole (10075-50-0)

Conditions	Yield
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-bromo-1H-indole (10075-50-0)

Conditions	Yield
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) → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With sodium ethanolate In ethanol Heating; Yield given;

ammonium salt of/the/ 5-bromo-indole-2-carboxylic acid → 5-bromo-1H-indole (10075-50-0)

Conditions	Yield
With glycerol

5-bromo-1H-indole (10075-50-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5-bromo-1H-indole-3-carboxaldehyde (877-03-2)

Conditions	Yield
With trichlorophosphate	100%
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) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-5-bromoindole (96546-77-9)

Conditions	Yield
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) + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → 1-(5-Bromo-1H-indol-3-yl)-4,5-dichloro-3-hydroxy-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions	Yield
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) + methyl iodide (74-88-4) → 5-bromo-1-methyl-H-indole (10075-52-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran	100%
With sodium hydride In dimethyl sulfoxide	99%
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) + di-tert-butyl dicarbonate (24424-99-5) → 5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3)

Conditions	Yield
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) + ethyl bromoacetate (105-36-2) → ethyl 2-(5-bromo-1H-indol-1-yl)acetate (726174-45-4)

Conditions	Yield
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) + triisopropylsilyl chloride (13154-24-0) → 5-bromo-1-triisopropylsilyl-1H-indole (128564-66-9)

Conditions	Yield
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) + methyl vinyl ketone (78-94-4) → 4-(5-bromo-1H-3-indolyl)-2-butanone

Conditions	Yield
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) + benzaldehyde (100-52-7) → phenyl(indol-5-yl)methanol

Conditions	Yield
With lithium dibutyl(isopropyl)magnesate In tetrahydrofuran	100%

5-bromo-1H-indole (10075-50-0) → 3-iodo-5-bromo-1H-indole

Conditions	Yield
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) + 5-bromo-1H-indole (10075-50-0) + dibutyldicarbonate → bromoindolecarboxylic Acid T-Butyl Ester

Conditions	Yield
In dichloromethane	100%

5-bromo-1H-indole (10075-50-0) + methyl 2-(diallylamino)-2-methoxyacetate (1069135-01-8) → methyl 2-(5-bromo-1H-indol-3-yl)-2-(diallylamino)acetate (1069135-03-0)

Conditions	Yield
With hafnium tetrakis(trifluoromethanesulfonate); chloro-trimethyl-silane In dichloromethane at 20℃; for 1h;	100%

5-bromo-1H-indole (10075-50-0) + phenylmethanethiol (100-53-8) → 5-(benzylthio)-1H-indole (92554-49-9)

Conditions	Yield
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) + 1-bromo-octane (111-83-1) → 5-bromo-1-octyl-1H-indole (1244769-53-6)

Conditions	Yield
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) + 5-bromo-1H-indole (10075-50-0) → N-2-Fluorobenzyl-5-bromoindole (676581-33-2)

Conditions	Yield
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) + Trichloroacetyl chloride (76-02-8) → 2,2,2-trichloro-1-(5-bromo-1H-indol-3-yl)ethan-1-one

Conditions	Yield
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) + methyl bromide (74-83-9) → 5-bromo-1-methyl-H-indole (10075-52-2)

Conditions	Yield
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) + ethyl-3,3,3-trifluoropyruvate (13081-18-0) → (S)-3,3,3-trifluoro-2-hydroxy-2-(5-bromoindol-3-yl)propionic acid ethyl ester

Conditions	Yield
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) + nitrostyrene (5153-67-3) → 5-bromo-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions	Yield
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) + benzaldehyde (100-52-7) → 3,3'-(phenylmethylene)bis-(5-bromo-1H-indole)

Conditions	Yield
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) + benzyl bromide (100-39-0) → 1-benzyl-5-bromo-1H-indole (10075-51-1)

Conditions	Yield
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) + 2-Methylphenylboronic acid (16419-60-6) → 5-(2-methylphenyl)-1H-indole

Conditions	Yield
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) + ammonium thiocyanate (1147550-11-5) → 5-bromo-3-thiocyanatoindole

Conditions	Yield
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) + 5-bromo-1H-indole (10075-50-0) + carbon monoxide (201230-82-2) → (1H-indol-5-yl)(4-methylpiperazin-1-yl)methanone (640734-92-5)

Conditions	Yield
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) + 1-phenylmethylpiperazine (2759-28-6) + carbon monoxide (201230-82-2) → N-benzyl-N'-(5-indolylcarbonyl)piperazine

Conditions	Yield
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) + 1-butyn-4-ol (927-74-2) → 4-(Indol-5-yl)-3-butyn-1-ol

Conditions	Yield
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) + 4-nitrobenzaldehdye (555-16-8) → 5-bromo-3-((5-bromo-1H-indol-3-yl)(4-nitrophenyl)methyl)-1H-indole

Conditions	Yield
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-bromoindoline (22190-33-6)

Conditions	Yield
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) + benzenesulfonyl chloride (98-09-9) → 1-Benzenesulfonyl-5-bromo-indole (118757-11-2)

Conditions	Yield
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) + propargyl bromide (106-96-7) → 5-bromo-1-(prop-2-yn-1-yl)-1H-indole

Conditions	Yield
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%

Upstream product

• 10075-49-7 5-BroMo-1,3-diMethyl-1H-indole 
• 10075-48-6 5-BROMO-3-METHYLINDOLE 
• 100754-78-7 2-ACETOXY-5-FLUOROBENZYLACETATE 
• 100754-69-6 2-morpholinomethyl-2',3',4'-trimethoxyacrylophenone 
• 1007542-22-4 AKOS PAO-0361 
• 1007542-01-9 AKOS PAO-0341 
• 1007541-94-7 1-ISOPROPYL-5-METHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID 
• 1007541-75-4 3-propyl-1H-pyrazole-4-carboxylic acid(SALTDATA: FREE) 
• 1007541-72-1 5-ethyl-1H-pyrazole-4-carboxylic acid 
• 1007541-19-6 1,3-diethyl-1H-pyrazol-4-amine 
• 1007-54-1 2-(benzylthio)ethanamine(SALTDATA: HCl) 
• 1007540-98-8 (1-ISOPROPYL-3,5-DIMETHYL-1H-PYRAZOL-4-YL)METHYLAMINE 
• 10075-40-8 Methadone tartrate 
• 100-75-4 Piperidine, 1-nitroso- 

Downstream Products

• 53330-94-2 5-Acetylindole 
• 1196-69-6 Indole-5-carboxaldehyde 
• 192182-55-1 1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER 
• 15861-24-2 5-Cyanoindole 
• 144104-59-6 5-Indolylboronic acid 
• 81881-74-5 C-(1H-INDOL-5-YL)-METHYLAMINE 

Recommend Products

• 877-03-2  5-bromo-1H-indole-3-carboxaldehyde 
• 93-61-8  N-methyl-N-phenylformamide 
• 7254-19-5  5-bromo-2-indolecarboxylic acid 
• 106-40-1  4-bromo-aniline 
• 1826-67-1  vinyl magnesium bromide 
• 586-78-7  para-nitrophenyl bromide 
• 66134-18-7  1H,1′H-5,5′-biindole 
• 2033-24-1  cycl-isopropylidene malonate 
• 122-78-1  phenylacetaldehyde 
• 100-52-7  benzaldehyde 
• 142667-63-8  4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne 
• 1631-26-1  1-benzyl-1H-pyrrole-2,5-dione 
• 98-88-4  benzoyl chloride 
• 195253-49-7  1-ethyl-5-bromo-1H-indole