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4-Chloroindole
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Name

4-Chloroindole

 EINECS 246-747-8
CAS No. 25235-85-2 Density 1.331 g/cm3
PSA 15.79000 LogP 2.82130
Solubility Insoluble in water Melting Point N/A
Formula C8H6ClN Boiling Point 293 °C at 760 mmHg
Molecular Weight 151.595 Flash Point 158.9 °C
Transport Information N/A Appearance Light-yellow liquid
Safety 26-36-36/37/39 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 25235-85-2 (4-Chloroindole) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

4-chloro-1H-indole;4-Choroindole;

Article Data 35

4-Chloroindole Synthetic route

81038-36-0

methyl 4-chloro-indole-1-carboxylate

25235-85-2

4-chloro-1H-indole

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

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
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