4-Chloroindole supplier | CasNO.25235-85-2

Name
4-Chloroindole
EINECS 246-747-8
CAS No. 25235-85-2
Article Data35
CAS DataBase
Density 1.331 g/cm³
Solubility Insoluble in water
Melting Point
Formula C₈H₆ClN
Boiling Point 293 °C at 760 mmHg
Molecular Weight 151.595
Flash Point 158.9 °C
Transport Information
Appearance Light-yellow liquid
Safety 26-36-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 4-chloro-1H-indole;4-Choroindole;
PSA 15.79000
LogP 2.82130

Synthetic route

: 81038-36-0
methyl 4-chloro-indole-1-carboxylate

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 100376-53-2
2-(2-amino-6-chlorophenyl)ethyl alcohol

: 25235-85-2
4-chloro-1H-indole

Conditions

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%

: 102493-68-5
2-(2-chloro-6-nitrophenyl)-ethanol

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 32991-06-3
3-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 89892-65-9
2,β-Dinitro-6-chlor-styrol

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 1244651-54-4
N-(3-chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)-2-hydroxy-2-methylpropanamide

: 25235-85-2
4-chloro-1H-indole

Conditions

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%

: 41910-64-9
4-chloroindoline

: 25235-85-2
4-chloro-1H-indole

Conditions

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%

: 101909-42-6
methyl 4-chloro-3-indolecarboxylate

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 83-42-1
6-chloro-2-nitrotoluene

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 25235-85-2
4-chloro-1H-indole

Conditions

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;

: 91523-33-0
4-Chloro-1-methoxy-1,3-dihydro-indol-2-one

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 121-73-3
3-Chloronitrobenzene

: 1826-67-1
vinyl magnesium bromide

A: 17422-33-2
6-chloroindole

B: 25235-85-2
4-chloro-1H-indole

C: 108-42-9
3-chloro-aniline

Conditions

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%

...Expand

: 320337-94-8
1-[(E)-2-(2-chloro-6-nitrophenyl)vinyl]pyrrolidine

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 24621-73-6
4-chloro-1H-indole-2-carboxylic acid

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 83-42-1
6-chloro-2-nitrotoluene

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 83-42-1
6-chloro-2-nitrotoluene

HNO3+H2SO4: HNO3+H2SO4

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 4769-97-5
4-nitro-1H-indoIe

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 78283-23-5
1-hydroxy-4-nitroindole

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 81038-30-4
4-amino-1-methoxycarbonylindole

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 81038-41-7
1-methoxycarbonyl-4-nitroindole

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 81038-27-9
methyl 2-hydroxy-2-(4-nitroindol-1-yl)-acetate

: 25235-85-2
4-chloro-1H-indole

Conditions

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

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

: 81038-26-8
methyl 2-(4-nitroindole-1-yl)oxyacetate

: 25235-85-2
4-chloro-1H-indole

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

: 942-24-5
3-methoxycarbonylindole

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 119114-47-5
2-(2-chlorophenyl)-N-methoxyacetamide

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 91523-29-4
N-chloro-2-(2-chlorophenyl)-N-methoxyacetamide

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 51512-09-5
2-(2-chlorophenyl)acetyl chloride

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 36892-19-0
(2-chloro-6-nitro-phenyl)-pyruvic acid

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 863870-77-3
3-chloro-2-iodophenyl N,N-dimethyl O-carbamate

: 25235-85-2
4-chloro-1H-indole

Conditions

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

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

: 1244651-34-0
N-(3-chloro-2-iodophenyl)-2-hydroxy-2-methylpropanamide

: 25235-85-2
4-chloro-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 6482-24-2
2-Bromoethyl methyl ether

: 1313042-80-6
5-chloro-1-(2-methoxyethyl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 41910-64-9
4-chloroindoline

Conditions

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;

: 25235-85-2
4-chloro-1H-indole

: 24424-99-5
di-tert-butyl dicarbonate

: 129822-46-4
tert-butyl 4-chloro-1H-indole-1-carboxylate

Conditions

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;

: 25235-85-2
4-chloro-1H-indole

: 36255-44-4
3-bromopropanal dimethyl acetal

: 4-chloro-1-(3,3-dimethoxypropyl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 155396-71-7
tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

: 4-chloro-3-[phenyl(phenylsulfonyl)methyl]-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 25603-67-2
9-phenyl-fluoren-9-ol

: 4-chloro-3-(9-phenyl-9H-fluoren-9-yl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 100-39-0
benzyl bromide

: 77801-60-6
4-chloro-1-benzyl-1H-indole

Conditions

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;

: 25235-85-2
4-chloro-1H-indole

: 95151-36-3
methyl oct-1-en-3-yl carbonate

: (R)-4-chloro-1-(oct-1-en-3-yl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 75-36-5
acetyl chloride

: 1261240-69-0
1-(4-chloro-1H-indol-1-yl)ethan-1-one

Conditions

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%

: 25235-85-2
4-chloro-1H-indole

: 201230-82-2
carbon monoxide

: 71-36-3
butan-1-ol

: 1334225-18-1
butyl 4-chloro-1H-indole-1-carboxylate

Conditions

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%

...Expand

: 25235-85-2
4-chloro-1H-indole

: 16212-05-8
(allylsulfonyl)benzene

: 4-chloro-1-(1-(phenylsulfonyl)propan-2-yl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: 4-chloro-N,N-dimethyl-1H-indole-1-carboxamide

Conditions

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;

: 25235-85-2
4-chloro-1H-indole

: C16H12Cl2N2

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 74-88-4
methyl iodide

: 77801-91-3
4-chloro-1-methyl-1H-indole

Conditions

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

: 673-32-5
1-Phenylprop-1-yne

: 25235-85-2
4-chloro-1H-indole

: (S)-4-chloro-3-(1-phenylallyl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 16419-60-6
2-Methylphenylboronic acid

: 4-(o-tolyl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 98-09-9
benzenesulfonyl chloride

: 896137-68-1
4-chloro-1-phenylsulfonyl-1H-indole

Conditions

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℃;

: 25235-85-2
4-chloro-1H-indole

: 87751-69-7
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

: C23H18ClN

Conditions

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

: 123-75-1
pyrrolidine

: 25235-85-2
4-chloro-1H-indole

: 587-04-2
3-Chlorobenzaldehyde

: 1634687-04-9
4-chloro-3-((3-chlorophenyl)(pyrrolidin-1-yl)methyl)-1H-indole

Conditions

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

...Expand

: 25235-85-2
4-chloro-1H-indole

: 1301176-55-5
ethyl 2-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate

: 1301176-78-2
ethyl 2-acetyl-5-(4-chloro-1H-indol-3-yl)-5-(4-methoxyphenyl)pentanoate

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 100-44-7
benzyl chloride

: 77801-60-6
4-chloro-1-benzyl-1H-indole

Conditions

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%

: 25235-85-2
4-chloro-1H-indole

: 2516-47-4
cyclopropanemethylamine

: 1248591-02-7
N-(cyclopropylmethyl)-1H-indol-4-amine

Conditions

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%

: 90-46-0
9-hydroxyxanthene

: 25235-85-2
4-chloro-1H-indole

: 1339112-99-0
4-chloro-3-(9H-xanthen-9-yl)-1H-indole

Conditions

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%

: 25235-85-2
4-chloro-1H-indole

: 98-88-4
benzoyl chloride

: 858230-84-9
(4-chloro-1H-indol-1-yl)(phenyl)methanone

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 104-88-1
4-chlorobenzaldehyde

: 109-77-3
malononitrile

: C18H11Cl2N3

Conditions

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

...Expand

: 25235-85-2
4-chloro-1H-indole

: 776-76-1
methyldiphenylsilane

: 4-chloro-1-(methyldiphenylsilyl)-1H-indole

Conditions

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

: 25235-85-2
4-chloro-1H-indole

: 1147550-11-5
ammonium thiocyanate

: 4-chloro-3-thiocyanato-1H-indole

Conditions

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%

4-Chloroindole Chemical Properties

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
Molecular formula:C₈H₆ClN
Molecular Weight: 151.59
EINECS: 246-747-8
Boiling point : 129-130 ^°C4 mm Hg(lit.)
Density : 1.259 g/mL at 25 °C(lit.)
Refractive index : n20/D 1.628(lit.)
Flash point : >230 ^°F
Storage temp. : 2-8^°C
Appearance:Light-Yellow Liquid

4-Chloroindole Safety Profile

Hazard Codes :

Xi,Xn
The Risk Statements information of 4-Chloroindole:
R36/37/38:Irritating to eyes, respiratory system and skin.;
The Safety Statements information of 4-Chloroindole:
S26:In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice.;
S37/39:Wear suitable gloves and eye/face protection.;
WGK Germany : 3
F : 10
Hazard Note : Irritant

Product Name

4-Chloroindole

Synthetic route

4-Chloroindole Chemical Properties

4-Chloroindole Safety Profile

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