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496-15-1

Basic Information
CAS No.: 496-15-1
Name: Indoline
Article Data: 242
Cas Database
Molecular Structure:
Molecular Structure of 496-15-1 (Indoline)
Formula: C8H9N
Molecular Weight: 119.166
Synonyms: Indoline(6CI,7CI,8CI);1-Azaindan;1H-Indoline;2,3-Dihydro-1H-indole;2,3-Dihydroindole;1H-Indole,2,3-dihydro-;
EINECS: 207-816-8
Density: 1.04 g/cm3
Melting Point: -21 °C
Boiling Point: 227.2 °Cat 760 mmHg
Flash Point: 92.8 °C
Solubility: 5 g/L (20 °C) in water
Appearance: Clear colorless to slightly brown liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 23-24/25-37/39-26
Transport Information: N/A
PSA: 12.03000
LogP: 1.79260
Synthetic route
132431-12-0

N-(benzyloxycarbonyl)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%
120-72-9

indole

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%
16078-30-1

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

A

496-15-1

1-indoline

B

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%
13078-80-3

2-(2-chlorophenyl)ethanamine

copper quinoline

496-15-1

1-indoline

Conditions
ConditionsYield
With sodium hydroxide96%
864424-24-8

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

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

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

496-15-1

1-indoline

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

2-(2-bromophenyl)ethanamine

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%
120-72-9

indole

52652-40-1

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

A

496-15-1

1-indoline

B

86-73-7

9H-fluorene

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

C18H16N4O

A

496-15-1

1-indoline

B

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%
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    Product Name: Indoline Synonyms: 1-Azaindan;2,3-dihydro-1h-indol;Dihydroindole;2,3-DIHYDROINDOLE;2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;2,3-DIHYDRO-1H-INDOLE;LABOTEST-BB LT01605668;INDOLINE CAS:

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Chemistry


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

Uses

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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

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.