N-(benzyloxycarbonyl)indoline
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% |
indolin-1-yl(pyridin-2-yl)methanone
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; |
1-indoline
Conditions | Yield |
---|---|
With potassium carbonate; mercaptoacetic acid In methanol at 0 - 25℃; Inert atmosphere; chemoselective reaction; | 96% |
1-indoline
Conditions | Yield |
---|---|
With potassium carbonate at 200℃; for 2h; Inert atmosphere; Sealed tube; | 96% |
2-(2-bromophenyl)ethanamine
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% |
indole
1,4,4a,9a-tetrahydro-fluorene
A
1-indoline
B
9H-fluorene
Conditions | Yield |
---|---|
palladium on activated carbon at 250℃; for 2h; | A 90% B 95% |
C18H16N4O
A
1-indoline
B
1-benzyl-1H-[1,2,3]triazol-4-carboxylic acid
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 80℃; for 4h; Temperature; Time; | A 95% B 82% |
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h; | A n/a B 95% |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3.5h; | A 94% B n/a |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; nitrogen; water | 93% |
1-benzenesulfonyl-2,3-dihydro-1H-indole
1-indoline
Conditions | Yield |
---|---|
With cesium fluoride supported on Celite at 120℃; for 2.5h; chemoselective reaction; | 91% |
Conditions | Yield |
---|---|
copper(I) chloride In benzene | 90.8% |
indole
1,2,3,4-tetrahydro-9H-fluorene
A
1-indoline
B
9H-fluorene
Conditions | Yield |
---|---|
A 90% B n/a |
1-(trifluoromethylsulfonyl)indoline
1-indoline
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 1h; Reflux; | 90% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature; | 89% |
1-indoline
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 0℃; desulfonation; | 88% |
1-indoline
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol at 100℃; for 24h; | 88% |
1-Acetyl-2,3-dihydro-1H-indole
1-indoline
Conditions | Yield |
---|---|
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
1-indoline
Conditions | Yield |
---|---|
With 3-azapentane-1,5-diamine at 130℃; for 12h; Sealed tube; | 86% |
2-(2-chlorophenyl)ethanamine
1-indoline
Conditions | Yield |
---|---|
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
1-indoline
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 2h; UV-irradiation; | 85% |
In d7-N,N-dimethylformamide Thermodynamic data; |
1-indoline
chloroacetyl chloride
2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone
Conditions | Yield |
---|---|
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
benzenesulfonyl chloride
1-benzenesulfonyl-2,3-dihydro-1H-indole
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
With pyridine for 18h; | 100% |
Conditions | Yield |
---|---|
Heating; | 100% |
With pyridine at 120℃; for 4h; Inert atmosphere; Schlenk technique; | 97% |
With pyridine at 120℃; for 4h; Inert atmosphere; Schlenk technique; | 97% |
Conditions | Yield |
---|---|
With sodium bicarbonate In water; toluene | 100% |
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% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane 1.) 0 deg C, 10 min, 2.) RT, 1 h; | 100% |
In tetrahydrofuran for 2h; Heating; | 63% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
trifluoroacetic anhydride
2,2,2-trifluoro-1-(indolin-1-yl)ethan-1-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
In dichloromethane at 0℃; for 1h; Inert atmosphere; | 100% |
In benzene at 0 - 5℃; | 96% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; sulfinylation; | 100% |
1-indoline
4-(bromomethyl)benzene-1-sulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 3h; Substitution; | 100% |
1-indoline
4-chloro-2,6-dimethoxypyrimidine-5-carboxaldehyde
5-formyl-4-(N-indolinyl)-2,6-dimethoxypyrimidine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 0.25h; Substitution; | 100% |
Conditions | Yield |
---|---|
In acetic acid at 90℃; for 3h; | 100% |
With sodium hydrogencarbonate In dichloromethane | 100% |
With sodium hydrogencarbonate In dichloromethane at 20℃; for 2h; | 100% |
1-indoline
N-tert-butyloxycarbonylpiperidin-4-one
tert-butyl 4-(indolin-1-yl) piperidine-1-carboxylate
Conditions | Yield |
---|---|
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
D-Glucose
1-(β-D-glucopyranosyl)indoline
Conditions | Yield |
---|---|
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
Allyl chloroformate
2,3-dihydroindole-1-carboxylic acid allyl ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 1h; | 100% |
1-indoline
2-Nitrobenzenesulfonyl chloride
1-((2-nitrophenyl)sulfonyl)indoline
Conditions | Yield |
---|---|
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
Piperonylic acid
1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole
Conditions | Yield |
---|---|
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
3-fluorobenzene-1-sulfonyl chloride
1-((3-fluorophenyl)sulfonyl)indoline
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
In pyridine at 20℃; for 20h; |
1-indoline
3-methylphenylsulfonyl chloride
1-(m-tolylsulfonyl)indoline
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
1-indoline
4-Fluorobenzenesulfonyl chloride
1-((4-fluorophenyl)sulfonyl)indoline
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
1-indoline
6-deoxy-L-galactose
1-(β-L-fucopyranosyl)indoline
Conditions | Yield |
---|---|
In ethanol; water for 20h; Reflux; | 100% |
1-indoline
3,4-dichlorobenzoyl chloride
(3,4-dichlorophenyl)(indolin-1-yl)methanone
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 0.0833333h; Solvent; Green chemistry; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Reflux; | 100% |
With potassium carbonate In acetonitrile Reflux; |
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 (CAS NO.496-15-1) is used in the pharmaceutical.
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. |
Reported in EPA TSCA Inventory.
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
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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