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| CAS No.: | 496-15-1 |
|---|---|
| Name: | Indoline |
| Article Data: | 242 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 23-24/25-37/39-26 |
| PSA: | 12.03000 |
| LogP: | 1.79260 |
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- 496-15-1
1-indoline
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; | A 97% B 2% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide | 96% |
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indolin-1-yl(pyridin-2-yl)methanone
- 496-15-1
1-indoline
| Conditions | Yield |
|---|---|
| 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; |
- 496-15-1
1-indoline
| Conditions | Yield |
|---|---|
| With potassium carbonate; mercaptoacetic acid In methanol at 0 - 25℃; Inert atmosphere; chemoselective reaction; | 96% |
- 496-15-1
1-indoline
| Conditions | Yield |
|---|---|
| With potassium carbonate at 200℃; for 2h; Inert atmosphere; Sealed tube; | 96% |
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- 496-15-1
1-indoline
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| palladium on activated carbon at 250℃; for 2h; | A 90% B 95% |
| Conditions | Yield |
|---|---|
| With water; lithium hydroxide In tetrahydrofuran; methanol at 80℃; for 4h; Temperature; Time; | A 95% B 82% |
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Chemistry
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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: 
Xi
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.