1484-27-1

Basic information

• Product Name: 3-Bromoindole
• Synonyms: 3-BROMO-1H-INDOLE;3-BROMOINDOLE;1H-INDOLE, 3-BROMO-;3-Bromoindole ,98%;3-Bromoindole (3-Bromo-1H-indole);3-BroMoindole, 97%, 97%
• CAS NO: 1484-27-1
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.04
• Mol File: 1484-27-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 60-65C
• Boiling Point: 154-155C/3Torr
• Flash Point: 145.5 °C
• Appearance: /
• Density: 1.66 g/cm³
• Vapor Pressure: 0.000738mmHg at 25°C
• Refractive Index: 1.711
• PKA: 15.33±0.30(Predicted)
• CAS DataBase Reference: 3-Bromoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromoindole(1484-27-1)
• EPA Substance Registry System: 3-Bromoindole(1484-27-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• RIDADR: UN 2811
• Hazardous Substances Data: 1484-27-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 1096, 1982 DOI: 10.1055/s-1982-30087

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

Synthetic route

indole (120-72-9) → 3-bromoindole (1484-27-1)

Conditions	Yield
With bromine In N,N-dimethyl-formamide at 20℃; for 2h;	97.27%
With bromine In N,N-dimethyl-formamide Ambient temperature;	96%
With bromine In N,N-dimethyl-formamide at 20℃;	96%

1-methyl-4-<2-(3-bromo-1-indolyl)>pyridinium iodide (113123-63-0) → 3-bromoindole (1484-27-1) + 4-ethenyl-1-methylpyridinium iodide (21351-43-9)

Conditions	Yield
With sodium hydroxide In water; acetone at 25℃; for 24h;	A 85% B n/a

phenyl (β-indolyl)iodonium trifluoroacetate (67765-96-2) → 3-bromoindole (1484-27-1) + iodobenzene (591-50-4)

Conditions	Yield
With lithium bromide In N,N-dimethyl-formamide at 100℃; for 2h;	A 75% B n/a

3-Indolylphenyliodonium Bromide (95873-88-4) → 3-bromoindole (1484-27-1)

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 2h;	64%
In dimethyl sulfoxide at 100℃; for 2h; Product distribution;	64%

1-benzoyl-3-bromo-indole (6299-36-1) → 3-bromoindole (1484-27-1)

Conditions	Yield
With sodium ethanolate

4-<2-(1-indolyl)ethyl>pyridine (13585-81-4) → 3-bromoindole (1484-27-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / N-bromosuccinimide / tetrahydrofuran / 24 h / 25 °C 2: 95 percent / acetone / 24 h / 25 °C 3: 85 percent / NaOH / acetone; H2O / 24 h / 25 °C View Scheme

4-<2-(3-bromo-1-indolyl)ethyl>pyridine (113123-59-4) → 3-bromoindole (1484-27-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / acetone / 24 h / 25 °C 2: 85 percent / NaOH / acetone; H2O / 24 h / 25 °C View Scheme

3-Indolylphenyliodonium betaine (53000-40-1) → 3-bromoindole (1484-27-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / Hydrobromic acid (48percent) / ethanol / 0.5 h / -15 °C 2: 64 percent / dimethylsulfoxide / 2 h / 100 °C View Scheme

3-bromoindole (1484-27-1) + benzenesulfonyl chloride (98-09-9) → 3-bromo-1-phenylsulfonyl indole (99655-68-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 1.5h; Cooling with ice;	97%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 0 - 20℃;	89%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate 1.) benzene, 5 min, 2.) 2 h; Yield given. Multistep reaction;
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In benzene at 20℃; for 1h;

3-bromoindole (1484-27-1) + p-toluenesulfonyl chloride (98-59-9) → 3-bromo-1-(4-methylbenzenesulfonyl)-1H-indole (90481-77-9)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; benzene for 1h; Heating / reflux;	96%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	2.95 g

3-bromoindole (1484-27-1) + Methyl 2-bromopropionate (5445-17-0) → 2-(3-bromo-indol-1-yl)-propionic acid methyl ester (486396-70-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃;	93%

2-methyl-1H-indole (95-20-5) + 3-bromoindole (1484-27-1) → 2'-methyl-1H,1'H-2,3'-biindole (88919-84-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature;	92%
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	92%

3-bromoindole (1484-27-1) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 3-bromo-1-(2-bromobenzyl)indole

Conditions	Yield
Stage #1: 3-bromoindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 1-Bromo-2-bromomethyl-benzene In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Schlenk technique;	89%

3-bromoindole (1484-27-1) + carbon dioxide (124-38-9) → 1H-indole-3-carboxylic acid (771-50-6)

Conditions	Yield
Stage #1: 3-bromoindole With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #3: carbon dioxide In tetrahydrofuran; hexane at -20℃; for 0.5h;	89%

NH-pyrazole (288-13-1) + 3-bromoindole (1484-27-1) → 2-(1H-pyrazol-1-yl)-1H-indole (1225068-04-1)

Conditions	Yield
at 70℃; for 4h;	88%
With trifluoroacetic acid In dichloromethane at 20℃; for 4h;
With trifluoroacetic acid In dichloromethane at 20℃; for 24h;	480 mg

3-bromoindole (1484-27-1) + 4-bromo-2-nitrophenylboronic acid → 3-(4-bromo-2-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere;	88%

3-bromoindole (1484-27-1) + 3-bromo-2-nitrophenylboronic acid → 3-(3-bromo-2-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere;	87%

3-bromoindole (1484-27-1) + 5-bromo-2-nitrophenylboronic acid → 3-(5-bromo-2-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere;	87%

3-bromoindole (1484-27-1) + 2-bromo-6-nitrophenylboronic acid → 3-(2-bromo-6-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere;	86%

1-methylindole (603-76-9) + 3-bromoindole (1484-27-1) + benzaldehyde (100-52-7) → 3-[(5-bromo-1H-indol-3-yl)(phenyl)methyl]-1-methyl-1H-indole (1092390-84-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 90℃; for 2h; Sealed tube;	86%

3-bromoindole (1484-27-1) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → C29H32BrNO

Conditions	Yield
With phosphoric acid In water at 100℃; for 12h; Inert atmosphere; Schlenk technique;	86%

indole (120-72-9) + 3-bromoindole (1484-27-1) → 3-(2-indolyl)indole (27393-85-7)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	85%

indole (120-72-9) + 3-bromoindole (1484-27-1) → 3-(2-indolyl)indole (27393-85-7) + 2,3-dihydro-1H,1'H-[2,3']biindolyl (6637-10-1) + 2-(3-indolyl)-3-(3-indolyl)indole + 2-(3-indolyl)-3-(2-indolyl)indole (88919-86-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	A 85% B n/a C n/a D n/a

3-bromoindole (1484-27-1) → 2-bromo-3-chloroindole (108438-52-4)

Conditions	Yield
With sulfuryl dichloride In diethyl ether at 0℃; for 1h;	85%

3-bromoindole (1484-27-1) → 3-bromo-2-chloroindole (108438-53-5)

Conditions	Yield
With thionyl chloride In diethyl ether at 0℃; for 1h;	85%

3-bromoindole (1484-27-1) + Diphenylphosphine oxide (4559-70-0) → 3-bromo-2-diphenylphosphinylindole

Conditions	Yield
With manganese triacetate In acetic acid at 50℃; for 1h;	84%
With magnesium(II) nitrate; silver carbonate In acetonitrile at 60℃; Molecular sieve;	79%

3-bromoindole (1484-27-1) + pyrrole (109-97-7) → 2-(1H-pyrrol-2-yl)-1H-indole (88919-82-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature;	83%
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	83%
With trifluoroacetic acid In dichloromethane at 20℃;	83%
With trifluoroacetic acid In dichloromethane at 20℃; for 4h;

3-bromoindole (1484-27-1) + 2-phenyl-indole (948-65-2) → 3-(indol-2'-yl)-2-phenylindole (91107-11-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature;	82%

3-bromoindole (1484-27-1) + 4,6-dimethoxy-2,3-diphenyl-1H-indole (91107-10-7) → 7-(indol-2'-yl)-4,6-dimethoxy-2,3-diphenylindole (91107-13-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.25h; Ambient temperature;	80%

3-bromoindole (1484-27-1) + bromobenzene (108-86-1) → 3-bromo-1-phenyl-1H-indole

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 95℃; for 4h;	79%
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 95℃; for 4h;	75%

3-bromoindole (1484-27-1) + calcium carbide (75-20-7) → 3-bromo-1-vinyl-1H-indole

Conditions	Yield
With caesium carbonate In water; dimethyl sulfoxide at 100℃; for 12h; Sealed tube;	78%

N-Methylpyrrole (96-54-8) + 3-bromoindole (1484-27-1) → 2-(1-methyl-1H-pyrrol-2-yl)-1H-indole (94742-32-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature;	76%
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	76%

3-bromoindole (1484-27-1) → 2,3-dibromo-1H-indole (108438-54-6)

Conditions	Yield
With bromine In dichloromethane at 0℃;	76%

1-bromo-4-butene (5162-44-7) + 3-bromoindole (1484-27-1) → 3-bromo-1-(but-3-enyl)-1H-indole

Conditions	Yield
Stage #1: 3-bromoindole With potassium carbonate In acetonitrile at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-4-butene In acetonitrile Inert atmosphere;	73%

3-bromoindole (1484-27-1) + (9H-carbazol-3-yl)boronic acid → 3-(indol-3-yl)carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	71%

Upstream product

• 120-72-9 indole 
• 6299-36-1 1-benzoyl-3-bromo-indole 
• 113123-63-0 1-methyl-4-<2-(3-bromo-1-indolyl)>pyridinium iodide 
• 53000-40-1 3-Indolylphenyliodonium betaine 
• 113123-59-4 4-<2-(3-bromo-1-indolyl)ethyl>pyridine 
• 13585-81-4 4-<2-(1-indolyl)ethyl>pyridine 
• 95873-88-4 3-Indolylphenyliodonium Bromide 
• 67765-96-2 phenyl (β-indolyl)iodonium trifluoroacetate 

Downstream Products

• 27393-85-7 3-(2-indolyl)indole 
• 109005-09-6 2-(5,12-dihydroindolo[3,2-a]carbazol-6-yl)aniline 
• 109005-10-9 10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene 
• 88919-86-2 2-(3-indolyl)-3-(2-indolyl)indole 
• 6637-10-1 2,3-dihydro-1H,1'H-[2,3']biindolyl 
• 6941-73-7 2-(2,2-di(1H-indol-3-yl)ethyl)aniline 
• 65439-77-2 2,3'-(o-aminophenethylidene)di-indole 
• 109023-31-6 2-(5-Methyl-7,12-dihydro-7,12-diaza-indeno[1,2-a]fluoren-6-yl)-phenylamine 
• 109005-16-5 2'''-methyl-2,3'-2',3''-2'',3'''-tetraindolyl 
• 88919-84-0 2'-methyl-1H,1'H-2,3'-biindole 
• 88919-87-3 3-Methyl-2,3'-bi-indolyl 
• 91107-13-0 7-(indol-2'-yl)-4,6-dimethoxy-2,3-diphenylindole 
• 115920-44-0 carbazomycin G 
• 1621087-22-6 C₂₁H₁₉NO₅S 

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