Product Name

  • Name

    7-indolinecarbonitrile

  • EINECS
  • CAS No. 115661-82-0
  • Article Data3
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • Melting Point
  • Formula C9H8N2
  • Boiling Point 305.2 °C at 760 mmHg
  • Molecular Weight 144.176
  • Flash Point 138.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 115661-82-0 (7-indolinecarbonitrile)
  • Hazard Symbols
  • Synonyms 1H-Indole-7-carbonitrile, 2,3-dihydro-;Indolin-7-carbonitril;Indoline-7-carbonitrile;2,3-Dihydro-1H-indole-7-carbonitrile;
  • PSA 35.82000
  • LogP 1.66428

Synthetic route

1-indoline
496-15-1

1-indoline

methanolic sodium methanolate

methanolic sodium methanolate

trichloroacetonitrile
545-06-2

trichloroacetonitrile

7-cyanoindoline
115661-82-0

7-cyanoindoline

Conditions
ConditionsYield
With BCl3 In methanol; hexane; pentan-1-ol; water; toluene60.5%
...Expand
1-indoline
496-15-1

1-indoline

trichloroacetonitrile
545-06-2

trichloroacetonitrile

7-cyanoindoline
115661-82-0

7-cyanoindoline

Conditions
ConditionsYield
With boron trichloride; potassium carbonate In methanol; dichloromethane; toluene58%
7-cyanoindoline
115661-82-0

7-cyanoindoline

3-chloropropyl benzoate
942-95-0

3-chloropropyl benzoate

1-(benzoyloxypropyl)-7-cyanoindoline hydrochloride

1-(benzoyloxypropyl)-7-cyanoindoline hydrochloride

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 10h;91%
7-cyanoindoline
115661-82-0

7-cyanoindoline

3-chloropropyl benzoate
942-95-0

3-chloropropyl benzoate

1-[3-(benzoyloxy)propyl]-7-cyanoindoline

1-[3-(benzoyloxy)propyl]-7-cyanoindoline

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl acetamide at 140℃; for 24h; Inert atmosphere;84%
7-cyanoindoline
115661-82-0

7-cyanoindoline

1H-indole-7-carbonitrile
96631-87-7

1H-indole-7-carbonitrile

Conditions
ConditionsYield
With oxygen; sodium t-butanolate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 4h;58%
7-cyanoindoline
115661-82-0

7-cyanoindoline

2,3-dihydro-1H-indole-7-carboxylic acid
15861-40-2

2,3-dihydro-1H-indole-7-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid
7-cyanoindoline
115661-82-0

7-cyanoindoline

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-2-oxo-ethyl)-carbamic acid ethyl ester
1269801-81-1

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-2-oxo-ethyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / -15 - 20 °C / Inert atmosphere
2.2: -15 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.2: -15 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-ethyl)-carbamic acid ethyl ester
1269801-83-3

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-ethyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / -15 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-carbamoyl-2,3-dihydro-1H-indol-5-yl}-1-methyl-ethyl)-carbamic acid ethyl ester
1269801-84-4

(2-{1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-carbamoyl-2,3-dihydro-1H-indol-5-yl}-1-methyl-ethyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / -15 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
4.1: dihydrogen peroxide / dimethyl sulfoxide / 0.25 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
4.1: dihydrogen peroxide / dimethyl sulfoxide / 0.25 h / 25 - 30 °C
4.2: 3 h / 25 - 30 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

5-(2-amino-propyl)-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydro-1H-indole-7-carboxylic acid amide
1269801-85-5

5-(2-amino-propyl)-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydro-1H-indole-7-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / -15 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
4.1: dihydrogen peroxide / dimethyl sulfoxide / 0.25 h / 25 - 30 °C
5.1: potassium hydroxide / toluene / 3 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C
2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.2: -15 °C
3.1: trifluoroacetic acid; triethylsilane / toluene / 6 h / 25 - 30 °C
4.1: dihydrogen peroxide / dimethyl sulfoxide / 0.25 h / 25 - 30 °C
4.2: 3 h / 25 - 30 °C
5.1: potassium hydroxide; water / toluene / 3 h / Reflux
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

N-<3-(tert-butyldimethylsiloxy)propyl>-p-toluenesulfonate
115306-83-7

N-<3-(tert-butyldimethylsiloxy)propyl>-p-toluenesulfonate

1-[3-(t-butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydro-1H-indole-7-carbonitrile
1269801-75-3

1-[3-(t-butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydro-1H-indole-7-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;
With potassium carbonate In N,N-dimethyl-formamide at 70℃;
7-cyanoindoline
115661-82-0

7-cyanoindoline

silodosin
160970-54-7

silodosin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 5 h / 30 °C
3.1: triethylsilane; trifluoroacetic acid / toluene / 6 h / 30 °C
4.1: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 750.08 Torr
5.1: potassium carbonate; tetrabutylammomium bromide; potassium iodide / water / 6 h / 80 °C
6.1: dihydrogen peroxide; sodium hydroxide / dimethyl sulfoxide / 4 h / 18 - 30 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

5-[(2R)-2-(benzylamino)-1-propanoyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindoline

5-[(2R)-2-(benzylamino)-1-propanoyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 5 h / 30 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

5-[(2R)-2-(benzylamino)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindoline

5-[(2R)-2-(benzylamino)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 5 h / 30 °C
3.1: triethylsilane; trifluoroacetic acid / toluene / 6 h / 30 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile
239463-72-0

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 5 h / 30 °C
3.1: triethylsilane; trifluoroacetic acid / toluene / 6 h / 30 °C
4.1: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 750.08 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: potassium iodide; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 24 h / 140 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Cooling with ice
2.2: 3 h / 25 °C
3.1: C24H22F3NO2 / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere
3.2: 12 h / 0 °C
4.1: palladium 10% on activated carbon / methanol / 6 h / 50 °C / 3750.38 Torr
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile
885340-11-4

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C
2.2: 5 h / 30 °C
3.1: triethylsilane; trifluoroacetic acid / toluene / 6 h / 30 °C
4.1: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 750.08 Torr
5.1: potassium carbonate; tetrabutylammomium bromide; potassium iodide / water / 6 h / 80 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium iodide; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 24 h / 140 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Cooling with ice
2.2: 3 h / 25 °C
3.1: C24H22F3NO2 / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere
3.2: 12 h / 0 °C
4.1: palladium 10% on activated carbon / methanol / 6 h / 50 °C / 3750.38 Torr
5.1: sodium carbonate / tert-butyl alcohol; ethanol / 34 h / 50 - 90 °C / Inert atmosphere
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

C20H18N2O3

C20H18N2O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium iodide; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 24 h / 140 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Cooling with ice
2.2: 3 h / 25 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

C22H23N3O5

C22H23N3O5

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium iodide; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 24 h / 140 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Cooling with ice
2.2: 3 h / 25 °C
3.1: C24H22F3NO2 / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere
3.2: 12 h / 0 °C
View Scheme
7-cyanoindoline
115661-82-0

7-cyanoindoline

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile
885340-13-6

1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium iodide; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 24 h / 140 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Cooling with ice
2.2: 3 h / 25 °C
3.1: C24H22F3NO2 / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere
3.2: 12 h / 0 °C
4.1: palladium 10% on activated carbon / methanol / 6 h / 50 °C / 3750.38 Torr
5.1: sodium carbonate / tert-butyl alcohol; ethanol / 34 h / 50 - 90 °C / Inert atmosphere
6.1: sodium hydroxide / methanol / 2.75 h / 0 - 25 °C / Inert atmosphere
6.2: 2.5 h / 25 °C / Cooling with ice
View Scheme

7-Cyanoindoline Specification

The 7-Cyanoindoline, with the CAS registry number 115661-82-0, has the systematic name of 2,3-dihydro-1H-indole-7-carbonitrile. It is a kind of organics, and should be stored at dry and cool environment. And the molecular formula of the chemical is C9H8N2.

The characteristics of 7-Cyanoindoline are as followings: (1)ACD/LogP: 1.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.4; (4)ACD/LogD (pH 7.4): 1.4; (5)ACD/BCF (pH 5.5): 6.83; (6)ACD/BCF (pH 7.4): 6.83; (7)ACD/KOC (pH 5.5): 137.58; (8)ACD/KOC (pH 7.4): 137.76; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 27.03 Å2; (13)Index of Refraction: 1.612; (14)Molar Refractivity: 42.17 cm3; (15)Molar Volume: 121.2 cm3; (16)Polarizability: 16.72×10-24cm3; (17)Surface Tension: 53.7 dyne/cm; (18)Density: 1.18 g/cm3; (19)Flash Point: 138.4 °C; (20)Enthalpy of Vaporization: 54.56 kJ/mol; (21)Boiling Point: 305.2 °C at 760 mmHg; (22)Vapour Pressure: 0.000836 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: N#Cc1cccc2c1NCC2
(2)InChI: InChI=1/C9H8N2/c10-6-8-3-1-2-7-4-5-11-9(7)8/h1-3,11H,4-5H2
(3)InChIKey: YABRSQUYXZGQBW-UHFFFAOYAU

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