25235-85-2

Basic information

• Product Name: 4-Chloroindole
• Synonyms: 4-CHLOROINDOLE;4-CHLORO-1H-INDOLE;TIMTEC-BB SBB004057;Indole, 4-chloro-;NSC 88141;1H-Indole,4-chloro-(9CI);4-CHLOROINDOLE 99%;4-chloroindole 25235-85-2
• CAS NO: 25235-85-2
• Molecular Formula: C₈H₆ClN
• Molecular Weight: 151.59
• EINECS: 246-747-8
• Product Categories: INDOLE;blocks;IndolesOxindoles;Indoles and derivatives;Halides;Pyrroles & Indoles;Indoles;Simple Indoles;Indole Derivatives;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks;Building Blocks;C7 to C10;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 25235-85-2.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 129-130 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow/liquid (clear)
• Density: 1.259 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00309mmHg at 25°C
• Refractive Index: n20/D 1.628(lit.)
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble50mg/mL, clear, colorless
• PKA: 16.10±0.30(Predicted)
• Water Solubility: insoluble
• Stability: Store in Refrigerator
• BRN: 114880
• CAS DataBase Reference: 4-Chloroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroindole(25235-85-2)
• EPA Substance Registry System: 4-Chloroindole(25235-85-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 25235-85-2(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Liquid

Uses

Indole derivative. Inhibitor

General Description

The nitrosation rate of 4-chloroindole and the stability of its nitrosated products were studied.

InChI:InChI=1/C8H6ClN/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H

Synthetic route

methyl 4-chloro-indole-1-carboxylate (81038-36-0) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With potassium hydroxide In methanol for 1h; Reflux;	99%
With sodium hydroxide In methanol for 0.25h; Heating;	79%

2-(2-amino-6-chlorophenyl)ethyl alcohol (100376-53-2) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
tris(triphenylphosphine)ruthenium(II) chloride In toluene for 6h; Heating;	92%
tris(triphenylphosphine)ruthenium(II) chloride In toluene for 6h; Rate constant; Heating;	92%
tris(triphenylphosphine)ruthenium(II) chloride In toluene Heating;	80%

2-(2-chloro-6-nitrophenyl)-ethanol (102493-68-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With hydrogen In o-xylene under 760.051 Torr; for 12h; Reflux;	75%
Multi-step reaction with 2 steps 1: H2 / 5percent Pd-C / ethyl acetate 2: 80 percent / RuCl2(PPh3)3 / toluene / Heating View Scheme
Multi-step reaction with 2 steps 1: 45 percent / Zn/CaCl2/H2O / ethanol / 8 h / Heating 2: 92 percent / RuCl2(PPh3)3 / toluene / 6 h / Heating View Scheme
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 0 - 25 °C 2: 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl acetamide / 12 h / 75 °C 3: zinc; acetic acid / 24 h / 70 °C 4: pyridine / dichloromethane / 0 - 25 °C 5: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 16 h / 70 °C / 760.05 Torr / Schlenk technique 6: potassium hydroxide / methanol / 1 h / Reflux View Scheme

3-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene (32991-06-3) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With acetic acid; zinc In methanol; dichloromethane Heating;	74%
With hydrazine hydrate In tetrahydrofuran; methanol at 10 - 20℃; Reduction; cyclization;	243.3 g
In benzene

2,β-Dinitro-6-chlor-styrol (89892-65-9) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With indium; acetic acid In benzene at 80℃; for 1h; Inert atmosphere;	74%

N-(3-chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)-2-hydroxy-2-methylpropanamide (1244651-54-4) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere;	73%
With sodium hydroxide In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere;	73%

4-chloroindoline (41910-64-9) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With oxygen; sodium t-butanolate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 4h;	63%
With monoamine oxidase D11 In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 168h; pH=7.8; Enzymatic reaction;	44%

methyl 4-chloro-3-indolecarboxylate (101909-42-6) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Heating;	61.7%

6-chloro-2-nitrotoluene (83-42-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Stage #1: 6-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 9h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis;	55%
Stage #1: 6-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In N,N-dimethyl-formamide at 110℃; for 8h; Leimgruber-Batcho indole synthesis; Inert atmosphere; Stage #2: With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 75℃; for 5h; Leimgruber-Batcho indole synthesis;

4-Chloro-1-methoxy-1,3-dihydro-indol-2-one (91523-33-0) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;	40%

3-Chloronitrobenzene (121-73-3) + vinyl magnesium bromide (1826-67-1) → 6-chloroindole (17422-33-2) + 4-chloro-1H-indole (25235-85-2) + 3-chloro-aniline (108-42-9)

Conditions	Yield
In tetrahydrofuran at -40℃; Yield given;	A n/a B n/a C 32%
In tetrahydrofuran at -40℃; Yields of byproduct given;	A n/a B n/a C 32%

1-[(E)-2-(2-chloro-6-nitrophenyl)vinyl]pyrrolidine (320337-94-8) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 75℃; for 5h;	32%

4-chloro-1H-indole-2-carboxylic acid (24621-73-6) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With quinoline; copper(l) chloride Erhitzen auf Siedetemp.;
With quinoline; copper oxide-chromium oxide at 215℃;
at 255℃;

1-[(E)-2-(2-Chloro-6-nitro-phenyl)-vinyl]-piperidine → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
With titanium(III) chloride; ammonium acetate In acetone Yield given;

6-chloro-2-nitrotoluene (83-42-1) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / CuI; DMF / 0.33 h / 180 °C / 6000.6 - 7500.75 Torr / microwave irradiation 2: 74 percent / Zn; AcOH / methanol; CH2Cl2 / Heating View Scheme
Multi-step reaction with 2 steps 1: dimethylformamide / 80 h / 110 °C 2: 243.3 g / aq. hydrazine hydrate / tetrahydrofuran; methanol / 10 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: DMSO, TritonB / methanol 2: H2 / 5percent Pd-C / ethyl acetate 3: 80 percent / RuCl2(PPh3)3 / toluene / Heating View Scheme

6-chloro-2-nitrotoluene (83-42-1) + HNO3+H2SO4 → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Triton B, 2.) Zn, CaCl2 / 1.) Me2SO, 95 deg C, 1 h, 2.) H2O, reflux 2: 92 percent / RuCl2(PPh3)3 / toluene / 6 h / Heating View Scheme

4-nitro-1H-indoIe (4769-97-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl-formamide / 4 h 2: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 3: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 4: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

1-hydroxy-4-nitroindole (78283-23-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / methanol / 16 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 3: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 4: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: sodium hydroxide / methanol / 0.25 h / Heating View Scheme
Multi-step reaction with 5 steps 1: triethylamine / methanol / 43 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 3: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 4: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: sodium hydroxide / methanol / 0.25 h / Heating View Scheme
Multi-step reaction with 5 steps 1: ethyl bromoacetate; triethylamine / methanol / 92.5 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 3: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 4: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: sodium hydroxide / methanol / 0.25 h / Heating View Scheme
Multi-step reaction with 6 steps 1: triethylamine / methanol / 16 h / Ambient temperature 2: triethylamine / methanol / 16 h / Ambient temperature 3: sodium hydride / N,N-dimethyl-formamide / 4 h 4: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 5: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 6: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

4-amino-1-methoxycarbonylindole (81038-30-4) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 2: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

1-methoxycarbonyl-4-nitroindole (81038-41-7) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 2: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 3: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

methyl 2-hydroxy-2-(4-nitroindol-1-yl)-acetate (81038-27-9) → 4-chloro-1H-indole (25235-85-2)

Conditions

Yield

Multi-step reaction with 5 steps 1: sodium hydrogencarbonate / methanol; water / 0.08 h / Heating 2: sodium hydride / N,N-dimethyl-formamide / 4 h 3: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 4: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

methyl 2-(4-nitroindole-1-yl)oxyacetate (81038-26-8) → 4-chloro-1H-indole (25235-85-2)

Conditions

Yield

Multi-step reaction with 5 steps 1: triethylamine / methanol / 16 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 3: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 4: hydrogenchloride; copper(l) chloride; sodium nitrite / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: sodium hydroxide / methanol / 0.25 h / Heating View Scheme

3-methoxycarbonylindole (942-24-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TTFA, 2.) CuCl2 / 1.) TFA, room temp., 2 h; 2.) DMF, 120 deg C, 1 h 2: 61.7 percent / 40percent NaOH / methanol / 1.5 h / Heating View Scheme

2-(2-chlorophenyl)-N-methoxyacetamide (119114-47-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / tert-butyl hypochlorite / CH2Cl2 / 0.33 h / 0 °C 2: 71 percent / Ag2CO3, trifluoroacetic acid / 0.5 h / 0 °C 3: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating View Scheme

N-chloro-2-(2-chlorophenyl)-N-methoxyacetamide (91523-29-4) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / Ag2CO3, trifluoroacetic acid / 0.5 h / 0 °C 2: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating View Scheme

2-(2-chlorophenyl)acetyl chloride (51512-09-5) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / sodium carbonate / H2O; benzene / 5 h / Ambient temperature 2: 97 percent / tert-butyl hypochlorite / CH2Cl2 / 0.33 h / 0 °C 3: 71 percent / Ag2CO3, trifluoroacetic acid / 0.5 h / 0 °C 4: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating View Scheme

(2-chloro-6-nitro-phenyl)-pyruvic acid (36892-19-0) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Fe(OH)2; aqueous NH3 2: copper (I)-chloride; quinoline / Erhitzen auf Siedetemp. View Scheme

3-chloro-2-iodophenyl N,N-dimethyl O-carbamate (863870-77-3) → 4-chloro-1H-indole (25235-85-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol / Reflux 2.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 5.5 h / 40 °C / Inert atmosphere 5.1: sodium hydroxide / N,N-dimethyl-formamide / 4 h / 140 °C / Inert atmosphere View Scheme

N-(3-chloro-2-iodophenyl)-2-hydroxy-2-methylpropanamide (1244651-34-0) → 4-chloro-1H-indole (25235-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 5.5 h / 40 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 4 h / 140 °C / Inert atmosphere View Scheme

4-chloro-1H-indole (25235-85-2) + 2-Bromoethyl methyl ether (6482-24-2) → 5-chloro-1-(2-methoxyethyl)-1H-indole (1313042-80-6)

Conditions	Yield
With sodium hydride; sodium iodide In N,N-dimethyl-formamide; mineral oil at 0℃; for 2.16667h;	100%

4-chloro-1H-indole (25235-85-2) → 4-chloroindoline (41910-64-9)

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide	99%
With sodium cyanoborohydride; acetic acid at 0 - 20℃; Inert atmosphere;	89%
With sodium cyanoborohydride; acetic acid for 3h; Ambient temperature;

4-chloro-1H-indole (25235-85-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 4-chloro-1H-indole-1-carboxylate (129822-46-4)

Conditions	Yield
With dmap In tetrahydrofuran at 20℃;	99%
With dmap In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Sealed tube;	91%
With dmap In dichloromethane at 20℃; for 0.75h;

4-chloro-1H-indole (25235-85-2) + 3-bromopropanal dimethyl acetal (36255-44-4) → 4-chloro-1-(3,3-dimethoxypropyl)-1H-indole

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 5h;	99%

4-chloro-1H-indole (25235-85-2) + tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7) → 4-chloro-3-[phenyl(phenylsulfonyl)methyl]-1H-indole

Conditions	Yield
With dipotassium peroxodisulfate In toluene at 20℃; for 48h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; regioselective reaction;	99%

4-chloro-1H-indole (25235-85-2) + 9-phenyl-fluoren-9-ol (25603-67-2) → 4-chloro-3-(9-phenyl-9H-fluoren-9-yl)-1H-indole

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 60℃; for 4h; Sealed tube;	98%

4-chloro-1H-indole (25235-85-2) + benzyl bromide (100-39-0) → 4-chloro-1-benzyl-1H-indole (77801-60-6)

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 20h;	97%
Stage #1: 4-chloro-1H-indole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
Stage #1: 4-chloro-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 45℃; for 1h; Inert atmosphere;

4-chloro-1H-indole (25235-85-2) + methyl oct-1-en-3-yl carbonate (95151-36-3) → (R)-4-chloro-1-(oct-1-en-3-yl)-1H-indole

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C39H51N2O3P In acetonitrile at 100℃; for 36h; enantioselective reaction;	97%

4-chloro-1H-indole (25235-85-2) + acetyl chloride (75-36-5) → 1-(4-chloro-1H-indol-1-yl)ethan-1-one (1261240-69-0)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.75h;	96%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 1h; Inert atmosphere; Sealed tube;	64%

4-chloro-1H-indole (25235-85-2) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → butyl 4-chloro-1H-indole-1-carboxylate (1334225-18-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; oxygen; copper diacetate; dimethyl sulfoxide; triphenylphosphine In toluene at 100℃; under 760.051 Torr; for 36h; regioselective reaction;	95%

4-chloro-1H-indole (25235-85-2) + (allylsulfonyl)benzene (16212-05-8) → 4-chloro-1-(1-(phenylsulfonyl)propan-2-yl)-1H-indole

Conditions	Yield
With potassium tert-butylate In toluene at 22℃; for 0.166667h; Inert atmosphere; Sealed tube; regioselective reaction;	95%

4-chloro-1H-indole (25235-85-2) + N,N-Dimethylcarbamoyl chloride (79-44-7) → 4-chloro-N,N-dimethyl-1H-indole-1-carboxamide

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 75℃; for 3h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In N,N-dimethyl-formamide at 75℃; Inert atmosphere;	94%
Stage #1: 4-chloro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0 - 75℃; Inert atmosphere; Schlenk technique; Stage #2: N,N-Dimethylcarbamoyl chloride In N,N-dimethyl-formamide at 0 - 75℃; Inert atmosphere; Schlenk technique;	94%
With potassium hydroxide 1.) THF, RT, 15 min, 2.) THF, RT, 4 h; Multistep reaction;
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane Inert atmosphere; Reflux;

4-chloro-1H-indole (25235-85-2) → C16H12Cl2N2

Conditions	Yield
With bismuth(III) chloride In dichloromethane at 20℃; for 6h;	94%

4-chloro-1H-indole (25235-85-2) + methyl iodide (74-88-4) → 4-chloro-1-methyl-1H-indole (77801-91-3)

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 5h;	93%
Stage #1: 4-chloro-1H-indole With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: methyl iodide In tetrahydrofuran
Stage #1: 4-chloro-1H-indole With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: methyl iodide In tetrahydrofuran

1-Phenylprop-1-yne (673-32-5) + 4-chloro-1H-indole (25235-85-2) → (S)-4-chloro-3-(1-phenylallyl)-1H-indole

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; diphenyl hydrogen phosphate; (R)-DTBM-BINAP at 60℃; Inert atmosphere; Glovebox; enantioselective reaction;	93%

4-chloro-1H-indole (25235-85-2) + 2-Methylphenylboronic acid (16419-60-6) → 4-(o-tolyl)-1H-indole

Conditions	Yield
With potassium phosphate; palladium diacetate; ruphos In tetrahydrofuran; toluene at 100℃; for 15h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	93%

4-chloro-1H-indole (25235-85-2) + benzenesulfonyl chloride (98-09-9) → 4-chloro-1-phenylsulfonyl-1H-indole (896137-68-1)

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran for 1h;	92%
Stage #1: 4-chloro-1H-indole With sodium hydride In tetrahydrofuran at 0℃; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃;

4-chloro-1H-indole (25235-85-2) + rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene (87751-69-7) → C23H18ClN

Conditions	Yield
With iodine In dichloromethane at 20℃; for 1h;	92%

pyrrolidine (123-75-1) + 4-chloro-1H-indole (25235-85-2) + 3-Chlorobenzaldehyde (587-04-2) → 4-chloro-3-((3-chlorophenyl)(pyrrolidin-1-yl)methyl)-1H-indole (1634687-04-9)

Conditions	Yield
In methanol at 30℃; for 72h;	92%

4-chloro-1H-indole (25235-85-2) + ethyl 2-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate (1301176-55-5) → ethyl 2-acetyl-5-(4-chloro-1H-indol-3-yl)-5-(4-methoxyphenyl)pentanoate (1301176-78-2)

Conditions	Yield
With manganese(II) chloride tetrahydrate In nitromethane at 80℃; for 23h;	91%

4-chloro-1H-indole (25235-85-2) + benzyl chloride (100-44-7) → 4-chloro-1-benzyl-1H-indole (77801-60-6)

Conditions	Yield
Stage #1: 4-chloro-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Cooling with ice; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 15h; Inert atmosphere;	91%

4-chloro-1H-indole (25235-85-2) + cyclopropanemethylamine (2516-47-4) → N-(cyclopropylmethyl)-1H-indol-4-amine (1248591-02-7)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Sealed vial;	90%

9-hydroxyxanthene (90-46-0) + 4-chloro-1H-indole (25235-85-2) → 4-chloro-3-(9H-xanthen-9-yl)-1H-indole (1339112-99-0)

Conditions	Yield
With betaine dihydrogenphosphate In octanol at 50℃;	90%
at 20℃; Ionic liquid;	85%
With 1,3-dichloro-1,1,3,3-tetrabutylstannoxane In dichloromethane at 20℃; for 10h;	85%

4-chloro-1H-indole (25235-85-2) + benzoyl chloride (98-88-4) → (4-chloro-1H-indol-1-yl)(phenyl)methanone (858230-84-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;	90%

4-chloro-1H-indole (25235-85-2) + 4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → C18H11Cl2N3

Conditions	Yield
With L-proline In ethanol at 20℃; for 72h;	90%

4-chloro-1H-indole (25235-85-2) + methyldiphenylsilane (776-76-1) → 4-chloro-1-(methyldiphenylsilyl)-1H-indole

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;	90%

4-chloro-1H-indole (25235-85-2) + ammonium thiocyanate (1147550-11-5) → 4-chloro-3-thiocyanato-1H-indole

Conditions	Yield
With oxygen In tetrahydrofuran at 25℃; under 750.075 Torr; for 10h; Irradiation;	90%
With copper(II) choride dihydrate; oxygen In ethanol at 20℃; for 24h; Irradiation;	86%

Upstream product

• 24621-73-6 4-chloro-1H-indole-2-carboxylic acid 
• 121-73-3 3-Nitrochlorobenzene 
• 1826-67-1 vinyl magnesium bromide 
• 100376-53-2 2-(2-amino-6-chlorophenyl)ethyl alcohol 
• 91523-33-0 4-Chloro-1-methoxy-1,3-dihydro-indol-2-one 
• 81038-36-0 methyl 4-chloro-indole-1-carboxylate 
• 101909-42-6 methyl 4-chloro-1H-indole-3-carboxylate 
• 32991-06-3 3-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 
• 6971-51-3 3-methoxybenzyl alcohol 
• 41910-64-9 4-chloroindoline 
• 301645-40-9 1-chloro-3-nitro-2-vinylbenzene 
• 115444-95-6 2-chloro-6-nitrophenethyl methanesulfonate 
• 118191-06-3 2-chloro-6-nitrobenzaldehyde N,N-dimethylenamine 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 

Downstream Products

• 858230-84-9 (4-chloro-1H-indol-1-yl)(phenyl)methanone 
• 2519-61-1 4-chloroindole-3-acetic acid 
• 102665-25-8 (4-chloro-indol-3-yl)-glyoxylic acid dibenzylamide 
• 35577-92-5 4-phenyl-1H-indole 
• 41910-64-9 4-chloroindoline 
• 480435-69-6 3-(4-chloro-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 876-72-2 4-chloroindole-3-carboxaldehyde 
• 175675-82-8 4-Chloro-3-(4-chloromethyl-benzoyl)-indole-1-carboxylic acid dimethylamide 
• 40247-57-2 4-chloro-3-dimethylaminomethylindole 
• 77801-60-6 4-chloro-1-benzyl-1H-indole 
• 881909-65-5 4-chloro-3-{2-(4-methoxyphenyl)-prop-2-yl}-1H-indole 
• 871351-38-1 (S)-4-chloro-1-(3-chloro-1-phenyl-propyl)-1H-indole 
• 1056165-93-5 4-chloro-1-(1-trityl-1H-imidazol-4-ylmethyl)-1H-indole 
• 1248590-97-7 4-(4-methyl-1,4-diazepan-1-yl)-1H-indole 

Relevant articles and documents

Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols

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