Product Name

  • Name

    Indoline

  • EINECS 207-816-8
  • CAS No. 496-15-1
  • Article Data242
  • CAS DataBase
  • Density 1.04 g/cm3
  • Solubility 5 g/L (20 °C) in water
  • Melting Point -21 °C
  • Formula C8H9N
  • Boiling Point 227.2 °Cat 760 mmHg
  • Molecular Weight 119.166
  • Flash Point 92.8 °C
  • Transport Information
  • Appearance Clear colorless to slightly brown liquid
  • Safety 23-24/25-37/39-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 496-15-1 (Indoline)
  • Hazard Symbols IrritantXi
  • Synonyms Indoline(6CI,7CI,8CI);1-Azaindan;1H-Indoline;2,3-Dihydro-1H-indole;2,3-Dihydroindole;1H-Indole,2,3-dihydro-;
  • PSA 12.03000
  • LogP 1.79260

Synthetic route

N-(benzyloxycarbonyl)indoline
132431-12-0

N-(benzyloxycarbonyl)indoline

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; ethylenediamine In tetrahydrofuran at 20℃; under 760 Torr; for 1.5h; Hydrogenation;100%
With boron trifluoride diethyl etherate; ethanethiol In chloroform for 14h; Ambient temperature;93%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 8h; Heating;22%
indole
120-72-9

indole

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 22502.3 Torr; for 10h;99%
With tetrahydroxydiboron; palladium on activated carbon In 2,2,2-trifluoroethanol; water at 40℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique;99%
With sodium cyanoborohydride; acetic acid at 20℃; for 10h; Cooling with ice;98%
1-Acetyl-2,3-dihydro-1H-indole
16078-30-1

1-Acetyl-2,3-dihydro-1H-indole

A

1-indoline
496-15-1

1-indoline

B

1-ethylindoline
5876-09-5

1-ethylindoline

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;A 97%
B 2%
2-(2-chlorophenyl)ethanamine
13078-80-3

2-(2-chlorophenyl)ethanamine

copper quinoline

copper quinoline

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With sodium hydroxide96%
indolin-1-yl(pyridin-2-yl)methanone
864424-24-8

indolin-1-yl(pyridin-2-yl)methanone

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 50℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);96%
With ammonium bromide; ethylenediamine at 50℃; for 5h; Reagent/catalyst; Solvent; Microwave irradiation;96%
With ammonium iodide; hydrazine hydrate In ethanol at 50℃; for 18h; Inert atmosphere; Sealed tube;85%
With water; sodium hydroxide In tetrahydrofuran; methanol at 50℃; for 24h;83%
With methanol; sodium hydroxide In tetrahydrofuran; water at 50℃; for 24h;
1-((4-nitrophenyl)sulfonyl)indoline

1-((4-nitrophenyl)sulfonyl)indoline

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With potassium carbonate; mercaptoacetic acid In methanol at 0 - 25℃; Inert atmosphere; chemoselective reaction;96%
3-(but-3-yn-1-ylamino)-2H-pyran-2-one

3-(but-3-yn-1-ylamino)-2H-pyran-2-one

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With potassium carbonate at 200℃; for 2h; Inert atmosphere; Sealed tube;96%
2-(2-bromophenyl)ethanamine
65185-58-2

2-(2-bromophenyl)ethanamine

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene at 140℃; for 24h; Solvent; Temperature; Inert atmosphere;95%
With 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.5h;92%
With potassium phosphate; N,N-diethylsalicylamide; copper (I) acetate In N,N-dimethyl-formamide at 35℃; for 12h;88%
indole
120-72-9

indole

1,4,4a,9a-tetrahydro-fluorene
52652-40-1

1,4,4a,9a-tetrahydro-fluorene

A

1-indoline
496-15-1

1-indoline

B

9H-fluorene
86-73-7

9H-fluorene

Conditions
ConditionsYield
palladium on activated carbon at 250℃; for 2h;A 90%
B 95%
C18H16N4O
1016013-16-3

C18H16N4O

A

1-indoline
496-15-1

1-indoline

B

1-benzyl-1H-[1,2,3]triazol-4-carboxylic acid
28862-12-6

1-benzyl-1H-[1,2,3]triazol-4-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 80℃; for 4h; Temperature; Time;A 95%
B 82%
indolin-1-yl(pyridin-2-yl)methanone
864424-24-8

indolin-1-yl(pyridin-2-yl)methanone

A

2-Picolinic acid
98-98-6

2-Picolinic acid

B

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h;A n/a
B 95%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
Stage #1: 2-aminophenethyl alcohol With thionyl chloride In 1,2-dimethoxyethane at 20℃;
Stage #2: In 1,2-dimethoxyethane; water at 60℃; Further stages.;
94%
With sodium hydroxide; benzenesulfonyl chloride
With zinc(II) chloride at 200℃;
C18H14N2O
785708-62-5

C18H14N2O

A

1-indoline
496-15-1

1-indoline

B

quinoline-2-carboxylic acid
93-10-7

quinoline-2-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3.5h;A 94%
B n/a
2-(2-chlorophenyl)ethanamine
13078-80-3

2-(2-chlorophenyl)ethanamine

cupric chloride

cupric chloride

ethanolamine
141-43-5

ethanolamine

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; nitrogen; water93%
1-benzenesulfonyl-2,3-dihydro-1H-indole
81114-41-2

1-benzenesulfonyl-2,3-dihydro-1H-indole

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With cesium fluoride supported on Celite at 120℃; for 2.5h; chemoselective reaction;91%
2-(2-chlorophenyl)ethanamine
13078-80-3

2-(2-chlorophenyl)ethanamine

ammonium

ammonium

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
copper(I) chloride In benzene90.8%
indole
120-72-9

indole

1,2,3,4-tetrahydro-9H-fluorene
17057-95-3

1,2,3,4-tetrahydro-9H-fluorene

A

1-indoline
496-15-1

1-indoline

B

9H-fluorene
86-73-7

9H-fluorene

Conditions
ConditionsYield
A 90%
B n/a
1-(trifluoromethylsulfonyl)indoline
1071493-89-4

1-(trifluoromethylsulfonyl)indoline

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1h; Reflux;90%
indole
120-72-9

indole

A

4,5,6,7-tetrahydroindole
13618-91-2

4,5,6,7-tetrahydroindole

B

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 150℃; under 38002.6 Torr; for 0.4h;A 10%
B 90%
With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8H(1-); hydrogen In tetrahydrofuran at 80℃; under 30003 Torr; for 66h;A n/a
B 84%
With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8Cl(1-); hydrogen; sodium triethylborohydride In toluene at 80℃; under 30003 Torr; for 66h;A n/a
B 84%
1-nitrosoindoline
7633-57-0

1-nitrosoindoline

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;89%
1-indolinetrimethylmethanesulfonamide

1-indolinetrimethylmethanesulfonamide

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 0℃; desulfonation;88%
C16H22N2O2

C16H22N2O2

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol at 100℃; for 24h;88%
1-Acetyl-2,3-dihydro-1H-indole
16078-30-1

1-Acetyl-2,3-dihydro-1H-indole

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;88%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;88%
2,3-dihydroindole-1-carboxylic acid methyl ester
89875-37-6

2,3-dihydroindole-1-carboxylic acid methyl ester

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With 3-azapentane-1,5-diamine at 130℃; for 12h; Sealed tube;86%
2-(2-chlorophenyl)ethanamine
13078-80-3

2-(2-chlorophenyl)ethanamine

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
With 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 10h;85%
With potassium phosphate; N,N-diethylsalicylamide; copper (I) acetate In N,N-dimethyl-formamide at 50℃; for 48h;78%
With copper(l) iodide; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 25℃; for 48h; Inert atmosphere;76%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 70℃; for 45h;71%
With sodium hydride; tert-butyl alcohol; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride; palladium diacetate In 1,4-dioxane for 4h;
(R)-indoline-carboxylic acid
763047-58-1

(R)-indoline-carboxylic acid

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
In dimethyl sulfoxide for 2h; UV-irradiation;85%
In d7-N,N-dimethylformamide Thermodynamic data;
1-indoline
496-15-1

1-indoline

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone
17133-48-1

2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;100%
With N,N-dimethyl acetamide at 0℃; for 0.0833333h; Green chemistry;89%
In acetone at 0 - 20℃; for 1h;63%
1-indoline
496-15-1

1-indoline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-benzenesulfonyl-2,3-dihydro-1H-indole
81114-41-2

1-benzenesulfonyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 1h;100%
With potassium trimethylsilonate In water at 20℃; for 0.5h; Concentration; Inert atmosphere;97%
With dmap; triethylamine In dichloromethane at 0 - 20℃;96%
1-indoline
496-15-1

1-indoline

bromocyane
506-68-3

bromocyane

N-cyano-indoline
90036-14-9

N-cyano-indoline

Conditions
ConditionsYield
100%
1-indoline
496-15-1

1-indoline

benzenesulfinic anhydride
13086-77-6

benzenesulfinic anhydride

1-Benzenesulfinyl-2,3-dihydro-1H-indole

1-Benzenesulfinyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With pyridine for 18h;100%
1-indoline
496-15-1

1-indoline

acetic anhydride
108-24-7

acetic anhydride

1-Acetyl-2,3-dihydro-1H-indole
16078-30-1

1-Acetyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
Heating;100%
With pyridine at 120℃; for 4h; Inert atmosphere; Schlenk technique;97%
With pyridine at 120℃; for 4h; Inert atmosphere; Schlenk technique;97%
1-indoline
496-15-1

1-indoline

benzyl chloride
100-44-7

benzyl chloride

1-benzyl-2,3-dihydro-1H-indole
6037-73-6

1-benzyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With sodium bicarbonate In water; toluene100%
Stage #1: 1-indoline With sodium hydrogencarbonate In water at 90℃;
Stage #2: benzyl chloride In water at 90℃;
99%
With cesium fluoride In acetonitrile for 48h; Heating;98%
1-indoline
496-15-1

1-indoline

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

ethyl α-oxo-α-(N-indolinyl)-acetate
131328-01-3

ethyl α-oxo-α-(N-indolinyl)-acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane 1.) 0 deg C, 10 min, 2.) RT, 1 h;100%
In tetrahydrofuran for 2h; Heating;63%
1-indoline
496-15-1

1-indoline

benzonitrile
100-47-0

benzonitrile

7-benzoyl-1H-indoline
33244-57-4

7-benzoyl-1H-indoline

Conditions
ConditionsYield
Stage #1: 1-indoline; benzonitrile With aluminum (III) chloride; water; boron trichloride In dichloromethane; toluene at 110℃;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 80℃; for 1h;
100%
Stage #1: 1-indoline; benzonitrile With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 110℃;
Stage #2: With hydrogenchloride; water at 80℃; for 1h;
100%
With aluminum (III) chloride; boron trichloride In toluene Friedel-Crafts Acylation; Inert atmosphere; Reflux;84%
1-indoline
496-15-1

1-indoline

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

N-(β-chloropropionyl)-indoline
64140-62-1

N-(β-chloropropionyl)-indoline

Conditions
ConditionsYield
In acetone at 70℃; for 3h;100%
In acetone at 70℃; for 3h; Inert atmosphere; Sealed tube;99%
In acetone for 1h; Reflux;73%
1-indoline
496-15-1

1-indoline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-1-(indolin-1-yl)ethan-1-one
90732-28-8

2,2,2-trifluoro-1-(indolin-1-yl)ethan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In dichloromethane at 0℃; for 1h; Inert atmosphere;100%
In benzene at 0 - 5℃;96%
1-indoline
496-15-1

1-indoline

indole
120-72-9

indole

Conditions
ConditionsYield
tris(triphenylphosphine)ruthenium(II) chloride In toluene for 6h; Rate constant; Mechanism; Heating;100%
With C21H32Cl4N2Ru In toluene for 6h; Reagent/catalyst; Heating;100%
With tert.-butylhydroperoxide; iron(III) chloride; C42H40Cu2N8 In water; acetonitrile at 60℃; for 16h;100%
1-indoline
496-15-1

1-indoline

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-2,3-dihydro-1H-indole
6037-73-6

1-benzyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
Stage #1: 1-indoline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
100%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.25h;99%
Stage #1: 1-indoline With sodium hydrogencarbonate In water at 90 - 95℃;
Stage #2: benzyl bromide In water at 90 - 95℃; for 5h;
93%
1-indoline
496-15-1

1-indoline

tert-butylsulfinyl chloride
31562-43-3

tert-butylsulfinyl chloride

1-indolinetrimethylmethanesulfinamide

1-indolinetrimethylmethanesulfinamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; sulfinylation;100%
1-indoline
496-15-1

1-indoline

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

1-(4-bromomethyl-benzenesulfonyl)-2,3-dihydro-1H-indole

1-(4-bromomethyl-benzenesulfonyl)-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
1-indoline
496-15-1

1-indoline

4-chloro-2,6-dimethoxypyrimidine-5-carboxaldehyde
134221-52-6

4-chloro-2,6-dimethoxypyrimidine-5-carboxaldehyde

5-formyl-4-(N-indolinyl)-2,6-dimethoxypyrimidine
202463-42-1

5-formyl-4-(N-indolinyl)-2,6-dimethoxypyrimidine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.25h; Substitution;100%
1-indoline
496-15-1

1-indoline

acetyl chloride
75-36-5

acetyl chloride

1-Acetyl-2,3-dihydro-1H-indole
16078-30-1

1-Acetyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
In acetic acid at 90℃; for 3h;100%
With sodium hydrogencarbonate In dichloromethane100%
With sodium hydrogencarbonate In dichloromethane at 20℃; for 2h;100%
1-indoline
496-15-1

1-indoline

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

tert-butyl 4-(indolin-1-yl) piperidine-1-carboxylate
400828-91-3

tert-butyl 4-(indolin-1-yl) piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 65℃; for 65h; Product distribution / selectivity;100%
With sodium tris(acetoxy)borohydride; acetic acid at 0 - 25℃; for 1h; Product distribution / selectivity;100%
Stage #1: 1-indoline; N-tert-butyloxycarbonylpiperidin-4-one With acetic acid In 1,2-dichloro-ethane at 0℃; for 0.166667h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 10 - 20℃; for 65h; Product distribution / selectivity;
100%
1-indoline
496-15-1

1-indoline

D-Glucose
2280-44-6

D-Glucose

1-(β-D-glucopyranosyl)indoline
39264-64-7, 39264-63-6, 40837-51-2

1-(β-D-glucopyranosyl)indoline

Conditions
ConditionsYield
In ethanol; water for 26h; Reflux;100%
In ethanol; water for 26h; Reflux;100%
In ethanol; water for 24h; Heating;95%
In ethanol; water for 24h;95%
In ethanol Reflux;
1-indoline
496-15-1

1-indoline

Allyl chloroformate
2937-50-0

Allyl chloroformate

2,3-dihydroindole-1-carboxylic acid allyl ester
792909-18-3

2,3-dihydroindole-1-carboxylic acid allyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 1h;100%
1-indoline
496-15-1

1-indoline

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

1-((2-nitrophenyl)sulfonyl)indoline
301355-05-5

1-((2-nitrophenyl)sulfonyl)indoline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
Stage #1: 1-indoline; 2-Nitrobenzenesulfonyl chloride at 20℃;
Stage #2: With sodium hydroxide for 0.666667h;
72%
With pyridine; dmap; triethylamine at 0 - 110℃; for 27.5h; Inert atmosphere;57%
1-indoline
496-15-1

1-indoline

Piperonylic acid
94-53-1

Piperonylic acid

1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole
40360-67-6

1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 2h; Inert atmosphere;100%
With PS-triphenylphosphane; iodine; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h;
1-indoline
496-15-1

1-indoline

3-fluorobenzene-1-sulfonyl chloride
701-27-9

3-fluorobenzene-1-sulfonyl chloride

1-((3-fluorophenyl)sulfonyl)indoline
893902-38-0

1-((3-fluorophenyl)sulfonyl)indoline

Conditions
ConditionsYield
With pyridine at 20℃;100%
In pyridine at 20℃; for 20h;
1-indoline
496-15-1

1-indoline

3-methylphenylsulfonyl chloride
1899-93-0

3-methylphenylsulfonyl chloride

1-(m-tolylsulfonyl)indoline
1024350-13-7

1-(m-tolylsulfonyl)indoline

Conditions
ConditionsYield
With pyridine at 20℃;100%
1-indoline
496-15-1

1-indoline

Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

1-(o-tolylsulfonyl)indoline
1374155-28-8

1-(o-tolylsulfonyl)indoline

Conditions
ConditionsYield
With pyridine at 20℃;100%
1-indoline
496-15-1

1-indoline

4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

1-((4-fluorophenyl)sulfonyl)indoline
314054-14-3

1-((4-fluorophenyl)sulfonyl)indoline

Conditions
ConditionsYield
With pyridine at 20℃;100%
1-indoline
496-15-1

1-indoline

3,4-dichlorobenzoyl chloride
3024-72-4

3,4-dichlorobenzoyl chloride

(3,4-dichlorophenyl)(indolin-1-yl)methanone
61589-15-9

(3,4-dichlorophenyl)(indolin-1-yl)methanone

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;100%
1-indoline
496-15-1

1-indoline

butyraldehyde
123-72-8

butyraldehyde

N-n-butyl-2,3-dihydroindole
5876-10-8

N-n-butyl-2,3-dihydroindole

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 0.0833333h; Solvent; Green chemistry;100%
1-indoline
496-15-1

1-indoline

4-(3-bromopropoxy)-3-methoxybenzaldehyde
148433-00-5

4-(3-bromopropoxy)-3-methoxybenzaldehyde

C19H21NO3

C19H21NO3

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;100%
With potassium carbonate In acetonitrile Reflux;

Indoline Chemical Properties


IUPAC Name: 2,3-Dihydro-1H-indole
Molecular Formula: C8H9N
Molecular Weight: 119.16 g/mol
SMILES: c12c(NCC1)cccc2
InChI: InChI=1/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
EINECS: 207-816-8
Classification Code: Drug / Therapeutic Agent
Product Categories: Intermediates; Indole / indoline / oxindole; Indole and Indoline; Indoles and derivatives; Pyrroles & Indoles; Indoline & Oxindole; Pyrroles & Indoles
Water Solubility: 5 g/L (20 °C)
Sensitive: Light Sensitive
Index of Refraction: 1.562 
Molar Refractivity: 37.16 cm3 
Molar Volume: 114.5 cm3 
Polarizability: 14.73×10-24 cm3 
Surface Tension: 38.9 dyne/cm 
Density: 1.04 g/cm3 
Flash Point: 92.8 °C 
Enthalpy of Vaporization: 46.38 kJ/mol 
Boiling Point: 227.2 °C at 760 mmHg 
Melting Point: -21 °C
storage temperature: 2-8 °C
Vapour Pressure of Indoline (CAS NO.496-15-1): 0.0783 mmHg at 25 °C

Indoline Uses

 Indoline (CAS NO.496-15-1) is used in the pharmaceutical.

Indoline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 238mg/kg (238mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1620, 1974.

Indoline Consensus Reports

Reported in EPA TSCA Inventory.

Indoline Safety Profile

A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-37/39-26 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes. 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: NL6906300
Hazard Note of Indoline (CAS NO.496-15-1): Irritant

Indoline Specification

  Indoline (CAS NO.496-15-1), its Synonyms are 1-Azaindan ; 2,3-Dihydro-1H-indole ; 2,3-Dihydroindole ; 1H-Indole, 2,3-dihydro- . Indoline is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound is based on the indole structure, but the 2-3 bond is saturated. It is clear colorless to slightly brown liquid.

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