1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine
A
indol-5-ol
B
5-benzyloxy-1H-indole
Conditions | Yield |
---|---|
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 9h; | A 1% B 99% |
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 15h; | A 3% B 96% |
With hydrogen; 5% rhodium-on-charcoal; nickel(II) nitrate In tetrahydrofuran; water at 20℃; for 23h; | A 0.4% B 93% |
1H-indole-5-boronic acid
indol-5-ol
Conditions | Yield |
---|---|
With water; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry; | 91% |
With C11H12ClNOPtS2; triethylamine In N,N-dimethyl-formamide at 20℃; Irradiation; | 48% |
With Oxone; potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 70℃; for 1h; chemoselective reaction; |
Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In ethanol Ambient temperature; | 90% |
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave; | 90% |
With palladium on activated charcoal; ethyl acetate Hydrogenation; |
Conditions | Yield |
---|---|
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry; | 84% |
5-(prop-2-ynynloxy)indole
indol-5-ol
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanolamine In water at 80℃; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux; | 71% |
With aluminium trichloride; benzene | |
With trimethylammonium heptachlorodialuminate In dichloromethane Heating; |
5-benzyloxy-2-nitrophenylacetonitrile
indol-5-ol
Conditions | Yield |
---|---|
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature; | 70% |
indol-5-ol
Conditions | Yield |
---|---|
With silver nitrate In dichloromethane at 20℃; for 1.5h; | 64% |
A
indol-5-ol
Conditions | Yield |
---|---|
In methanol for 10h; Reflux; | A 53% B 61% |
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 57% B 60% |
indole
A
6-hydroxy-1H-indole
B
indol-5-ol
C
7-Indolol
D
1H-indol-4-ol
Conditions | Yield |
---|---|
With dihydrogen peroxide; edetate disodium; iron(II) sulfate; ascorbic acid phosphate buffer (pH=7.2); | A 10% B 30% C 10% D 50% |
2,6-dimethylnitrobenzene
2,3-Dihydro-1H-indol-5-ol
A
indol-5-ol
B
2,6-dimethylaniline
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 35% B 33% |
Conditions | Yield |
---|---|
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -20℃; for 0.05h; | A 10% B 20% C 5% |
Conditions | Yield |
---|---|
With methanol; ammonia |
5-hydroxyindole-2-carboxylic acid
indol-5-ol
Conditions | Yield |
---|---|
With copper at 250℃; | |
With copper; glycerol at 225 - 230℃; |
2-amino-3-(2,5-dihydroxyphenyl)propanoic acid
indol-5-ol
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III) | |
3h electrolysis at +0.2 V, pH 7.02; Multistep reaction; |
1H-indol-5-yl acetate
A
indol-5-ol
B
1-(5-Hydroxy-1H-indol-4-yl)-ethanone
C
1-(5-Hydroxy-1H-indol-6-yl)-ethanone
Conditions | Yield |
---|---|
Irradiation; | A 36 % Chromat. B 40 % Chromat. C 6 % Chromat. |
Product distribution; Mechanism; Irradiation; | A 36 % Chromat. B 40 % Chromat. C 6 % Chromat. |
2,5-dihydroxyphenylethylamine
indol-5-ol
Conditions | Yield |
---|---|
1h electrolysis at +0.2 V, pH 7.48 buffer; Multistep reaction; | |
With ammonium hydroxide; air In methanol Yield given; |
indol-5-ol
Conditions | Yield |
---|---|
With palladium on activated charcoal In benzene for 3h; Heating; Yield given; |
N,N,N',N'-tetramethyl-para-phenylenediamine
5-Hydroxyindole radical
A
indol-5-ol
B
N,N,N',N'-Tetramethyl-benzene-1,4-diamine
Conditions | Yield |
---|---|
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation; |
4-(N,N-dimethylamino)phenol
5-Hydroxyindole radical
A
indol-5-ol
B
4-(N,N-dimethylamino)phenoxyl radical
Conditions | Yield |
---|---|
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation; |
indol-5-ol
Conditions | Yield |
---|---|
With water; silver(I) chloride und Behandeln der Reaktionsloesung mit Kalium-hexacianoferrat(III) und Natriumhydrogencarbonat; |
Conditions | Yield |
---|---|
at 220℃; |
indol-5-ol
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride Erwaermen des erhaltenen Oxims mit Essigsaeure und Acetanhydrid und Hydrieren des Reaktionsprodukts in Aethylacetat an Palladium/Kohle.; |
[4-(benzyloxy)phenyl]hydrazine
indol-5-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2SO4 / methanol / 3 h / Heating 2: MeOH / Pd/C / 20 °C / 760 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 66 percent / NH3 / tetrahydrofuran 2: BH3 / tetrahydrofuran 3: aq. NH3, air / methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BH3 / tetrahydrofuran 2: aq. NH3, air / methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: anhydrous K2CO3 / dimethylformamide 2: 67 percent / tBuOK / dimethylformamide / 0.5 h / -20 - -10 °C 3: 70 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature View Scheme |
indol-5-ol
tert-butyldimethylsilyl chloride
5-(tert-butyl-dimethyl-silanyloxy)-1H-indole
Conditions | Yield |
---|---|
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃; for 20h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h; | 100% |
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
In dichloromethane | 99% |
With triethylamine In dichloromethane at 0 - 20℃; | 83% |
With dmap; triethylamine In dichloromethane at 0℃; for 5h; | 69% |
With triethylamine In dichloromethane |
indol-5-ol
tert-butyl (1-benzyl-7-methyl-2-oxoindolin-3-ylidene)carbamate
Conditions | Yield |
---|---|
With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione In toluene at 25℃; for 12h; Friedel-Crafts Alkylation; enantioselective reaction; | 99% |
indol-5-ol
Conditions | Yield |
---|---|
With C32H28F6N4O3 In dichloromethane at -30℃; for 35h; Friedel-Crafts Alkylation; enantioselective reaction; | 99% |
indol-5-ol
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In toluene at -40℃; for 12h; Catalytic behavior; Concentration; Reagent/catalyst; Solvent; enantioselective reaction; | 99% |
With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In ethyl acetate at -30℃; enantioselective reaction; | 58% |
indol-5-ol
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In 1,2-dichloro-ethane at -20℃; for 12h; Catalytic behavior; Solvent; Temperature; enantioselective reaction; | 99% |
indol-5-ol
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In toluene at -40℃; for 12h; enantioselective reaction; | 99% |
indol-5-ol
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In toluene at -40℃; for 12h; enantioselective reaction; | 99% |
indol-5-ol
N-[2,5-Dichloro-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-benzenesulfonamide
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In toluene at -40℃; for 12h; enantioselective reaction; | 99% |
indol-5-ol
Conditions | Yield |
---|---|
With 1,1’-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl) thiourea) In toluene at -40℃; for 12h; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; sodium bromide In 1,4-dioxane at 120℃; under 750.075 Torr; for 24h; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 98% |
With potassium carbonate In acetone for 72h; Inert atmosphere; Schlenk technique; Reflux; | 84% |
In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With zinc diacetate at 50℃; for 17.33h; | 98% |
indol-5-ol
tert-butyl (1-benzyl-6-chloro-2-oxoindolin-3-ylidene)carbamate
Conditions | Yield |
---|---|
With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione In toluene at 25℃; for 12h; Friedel-Crafts Alkylation; enantioselective reaction; | 98% |
indol-5-ol
2-(2-nitroethenyl)thiophene
Conditions | Yield |
---|---|
With 3-((1R,2R)-2-(piperidin-1-yl)cyclohexylamino)-4-(4-(trifluoromethyl)phenylamino)cyclobut-3-ene-1,2-dione In chloroform at 4℃; Friedel-Crafts Alkylation; enantioselective reaction; | 98% |
4,6-dichloropyrimidine
indol-5-ol
5-(6-chloropyrimidin-4-yloxy)-1H-indole
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h; | 97.4% |
With sodium hydroxide In water; acetone at 65℃; for 1.16667h; | |
Stage #1: indol-5-ol With sodium hydroxide In water at -10 - 10℃; Stage #2: 4,6-dichloropyrimidine In water; acetone at 0℃; for 1.58333h; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h; |
Conditions | Yield |
---|---|
With potassium carbonate In butanone at 89℃; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | 82% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | 82% |
indol-5-ol
Conditions | Yield |
---|---|
Stage #1: indol-5-ol With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With fluorosulfonyl fluoride In acetonitrile at 20℃; for 5h; chemoselective reaction; | 97% |
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 97% |
indol-5-ol
Conditions | Yield |
---|---|
With (11aR)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In toluene at 60℃; for 4h; enantioselective reaction; | 97% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethyl borane In tetrahydrofuran; hexane at 50℃; for 24h; | 96% |
With {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; C21H10F12NOP In toluene at 50℃; for 20h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
Stage #1: indol-5-ol With bromamine B; sodium hydroxide; palladium dichloride In water; acetonitrile at 60℃; for 3.33333h; pH=12; Stage #2: In water Acidic conditions; | 96% |
With ruthenium trichloride; osmium(VIII) oxide; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 4.33333h; | 96% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate at 20℃; for 0.0333333h; neat (no solvent); | 96% |
Conditions | Yield |
---|---|
In neat (no solvent) at 90 - 100℃; for 44h; Sealed tube; | 96% |
Conditions | Yield |
---|---|
Stage #1: indol-5-ol; N-methylacridinium iodide With titanium(IV) oxide In butan-1-ol for 0.0833333h; Sonication; Green chemistry; Stage #2: In butan-1-ol at 20℃; for 5h; Irradiation; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With caesium carbonate In acetone at 20℃; | 95% |
With caesium carbonate In acetone Ambient temperature; | 87% |
With potassium carbonate In toluene Heating; |
Conditions | Yield |
---|---|
With C84H114F9N3O12S3 In water at 37℃; for 16h; Michael Addition; | 95% |
With C99H126N6O18S3 In methanol at 50℃; for 24h; Catalytic behavior; Solvent; Michael Addition; | 91% |
With N-Bromosuccinimide In dichloromethane at 40℃; for 5h; Friedel Crafts alkylation; | 89% |
With MoS2 supported on graphitic carbon nitride nanocomposit In water at 55℃; for 12h; Michael Addition; Green chemistry; |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate at 20℃; for 0.0333333h; neat (no solvent); | 95% |
indol-5-ol
Conditions | Yield |
---|---|
With iodine In methanol at 20℃; for 24h; regioselective reaction; | 95% |
indol-5-ol
4-nitrobenzaldehdye
3,3''-((4-nitrophenyl)methylene)bis(1H-indol-5-ol)
Conditions | Yield |
---|---|
With benzenesulfonic acid In acetonitrile at 20℃; for 0.166667h; Sonication; | 95% |
The IUPAC name of 5-Hydroxyindole is 1H-indol-5-ol. With the CAS registry number 1953-54-4, it is also named as 5-Hydroxy-1H-indole. The product's categories are Blocks; Indoles Oxindoles; Indole Derivative; Indoles and Derivatives; Pharmacetical; Indole; Indoles; Simple Indoles. Besides, it is beige to brown crystalline needles or powder, which should be stored at 0-6 °C. In addition, its molecular formula is C8H7NO and molecular weight is 133.15.
The other characteristics of this product can be summarized as: (1)EINECS: 217-782-6; (2)ACD/LogP: 0.97; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.97; (5)ACD/LogD (pH 7.4): 0.97; (6)ACD/BCF (pH 5.5): 3.22; (7)ACD/BCF (pH 7.4): 3.21; (8)ACD/KOC (pH 5.5): 80.3; (9)ACD/KOC (pH 7.4): 80.25; (10)#H bond acceptors: 2; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.739; (14)Molar Refractivity: 40.41 cm3; (15)Molar Volume: 100.3 cm3; (16)Surface Tension: 65.8 dyne/cm; (17)Density: 1.327 g/cm3; (18)Flash Point: 161.4 °C; (19)Melting Point: 107-108 °C; (20)Water Solubility: 3.83e+04 mg/l at 25 °c; (21)Enthalpy of Vaporization: 61.03 kJ/mol; (22)Boiling Point: 343.2 °C at 760 mmHg; (23)Vapour Pressure: 3.61E-05 mmHg at 25 °C.
Preparation of 5-Hydroxyindole: this chemical can be prepared by 5-Benzyloxy-indole.
This reaction needs NH4OCOH, 10percent Pd/C and Ethanol at ambient temperature. The yield is 90 %.
Uses of 5-Hydroxyindole: this chemical is used as organic intermediate. Additionally, it can react with Methanesulfonyl chloride to get Methanesulfonic acid 1H-indol-5-yl ester.
This reaction needs CH2Cl2. The yield is 99 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: c1cc2c(cc[nH]2)cc1O
(2)InChI: InChI=1/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
(3)InChIKey: LMIQERWZRIFWNZ-UHFFFAOYAS
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 453, 1974. | |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01920, |
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