1953-54-4

Basic information

• Product Name: 5-Hydroxyindole
• Synonyms: 5-Hydroxy-1H-indole;Hydroxy-5 indole;hydroxy-5indole;TIMTEC-BB SBB004214;1H-INDOL-5-OL;5-HYDROXYINDOLE;5-INDOLOL;INDOL-5-OL
• CAS NO: 1953-54-4
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• EINECS: 217-782-6
• Product Categories: blocks;IndolesOxindoles;indole derivative;Indoles and derivatives;pharmacetical;Indole;Indoles;Simple Indoles;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 1953-54-4.mol
• Article Data: 34

Chemical Properties

• Melting Point: 106-108 °C(lit.)
• Boiling Point: 245.66°C (rough estimate)
• Flash Point: 161.4 °C
• Appearance: beige/Crystalline Needles or Powder
• Density: 1.1475 (rough estimate)
• Vapor Pressure: 3.61E-05mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: 0-6°C
• Solubility: 38g/l
• PKA: 9.98±0.40(Predicted)
• Sensitive: Light Sensitive
• BRN: 112349
• CAS DataBase Reference: 5-Hydroxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxyindole(1953-54-4)
• EPA Substance Registry System: 5-Hydroxyindole(1953-54-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: NM2430000
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 1953-54-4(Hazardous Substances Data)

Usage

Chemical Properties

beige to brown crystalline needles or powder

Uses

Different sources of media describe the Uses of 1953-54-4 differently. You can refer to the following data:
1. ? ;Reactant for preparation of (oxoimidazolidinyl/oxopyrimidinyl)benzenesulfonates as antitumor agents and tubulin inhibitors1? ;Reactant for preparation of anthranilic acids2? ;Reactant for preparation of indole compounds as dopamine D2 receptor antagonists3? ;Reactant for preparation of naphthalimide- or carbazole-containing human β-adrenoceptor ligands4? ;Reactant for preparation of melanins as nature-inspired radioprotectors5? ;Reactant for preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors6
2. 5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptop han (T894800). 5-Hydroxyindole displayed weak inhibitory activity on human melanoma tyrosinase. 5-Hydroxyindole also showed inhibition of serotonin transport by blood platelets.
3. 5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptophan (T894800). 5-Hydroxyindole displayed weak inhibitory activity on human melanoma tyrosinase. 5-Hydroxyindole also showed inhibition of serotonin transport by blood platelets.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5579, 1954 DOI: 10.1021/ja01651a001The Journal of Organic Chemistry, 49, p. 4833, 1984 DOI: 10.1021/jo00199a017

InChI:InChI=1/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H

Synthetic route

1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine (153805-85-7) → indol-5-ol (1953-54-4) + 5-benzyloxy-1H-indole (1215-59-4)

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 (144104-59-6) → indol-5-ol (1953-54-4)

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;

5-benzyloxy-1H-indole (1215-59-4) → indol-5-ol (1953-54-4)

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;

oxygen (80937-33-3) + 1H-indole-5-boronic acid (144104-59-6) → indol-5-ol (1953-54-4)

Conditions	Yield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;	84%

5-(prop-2-ynynloxy)indole (153969-91-6) → indol-5-ol (1953-54-4)

Conditions	Yield
With palladium on activated charcoal; ethanolamine In water at 80℃; Inert atmosphere;	77%

5-methoxylindole (1006-94-6) → indol-5-ol (1953-54-4)

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 (15566-30-0) → indol-5-ol (1953-54-4)

Conditions	Yield
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature;	70%

C8H7NO → indol-5-ol (1953-54-4)

Conditions	Yield
With silver nitrate In dichloromethane at 20℃; for 1.5h;	64%

methyl (4S,6R)-6-(5-hydroxy-1H-indol-3-yl)-7-hydroxy-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxylate → indol-5-ol (1953-54-4) + methyl (S)-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylate

Conditions	Yield
In methanol for 10h; Reflux;	A 53% B 61%

2,3-Dihydro-1H-indol-5-ol (172078-33-0) + nitrobenzene (98-95-3) → indol-5-ol (1953-54-4) + aniline (62-53-3)

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 (120-72-9) → 6-hydroxy-1H-indole (2380-86-1) + indol-5-ol (1953-54-4) + 7-Indolol (2380-84-9) + 1H-indol-4-ol (2380-94-1)

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 (81-20-9) + 2,3-Dihydro-1H-indol-5-ol (172078-33-0) → indol-5-ol (1953-54-4) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 35% B 33%

indole (120-72-9) → 6-hydroxy-1H-indole (2380-86-1) + indol-5-ol (1953-54-4) + 1H-indol-4-ol (2380-94-1)

Conditions	Yield
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -20℃; for 0.05h;	A 10% B 20% C 5%

1H-indol-5-yl acetate (5594-91-2) → indol-5-ol (1953-54-4)

Conditions	Yield
With methanol; ammonia

5-hydroxyindole-2-carboxylic acid (21598-06-1) → indol-5-ol (1953-54-4)

Conditions	Yield
With copper at 250℃;
With copper; glycerol at 225 - 230℃;

2-amino-3-(2,5-dihydroxyphenyl)propanoic acid (26122-90-7) → indol-5-ol (1953-54-4)

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 (5594-91-2) → indol-5-ol (1953-54-4) + 1-(5-Hydroxy-1H-indol-4-yl)-ethanone (126963-80-2) + 1-(5-Hydroxy-1H-indol-6-yl)-ethanone (126963-81-3)

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 (21581-41-9) → indol-5-ol (1953-54-4)

Conditions	Yield
1h electrolysis at +0.2 V, pH 7.48 buffer; Multistep reaction;
With ammonium hydroxide; air In methanol Yield given;

2,3-Dihydro-indol-5-one → indol-5-ol (1953-54-4)

Conditions	Yield
With palladium on activated charcoal In benzene for 3h; Heating; Yield given;

N,N,N',N'-tetramethyl-para-phenylenediamine (100-22-1) + 5-Hydroxyindole radical (80792-63-8) → indol-5-ol (1953-54-4) + N,N,N',N'-Tetramethyl-benzene-1,4-diamine (100-22-1)

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

4-(N,N-dimethylamino)phenol (619-60-3) + 5-Hydroxyindole radical (80792-63-8) → indol-5-ol (1953-54-4) + 4-(N,N-dimethylamino)phenoxyl radical (54737-34-7)

Conditions	Yield
With potassium hydroxide In water Rate constant; Equilibrium constant; Irradiation;

hydrobromide of 2,5-dihydroxy-phenethylamine → indol-5-ol (1953-54-4)

Conditions	Yield
With water; silver(I) chloride und Behandeln der Reaktionsloesung mit Kalium-hexacianoferrat(III) und Natriumhydrogencarbonat;

5-methoxylindole (1006-94-6) + N-methyl-aniline hydrobromide → indol-5-ol (1953-54-4)

Conditions	Yield
at 220℃;

sodium-salt of/the/ <5-benzyloxy-2-nitro-phenyl>-pyruvic acid → indol-5-ol (1953-54-4)

Conditions	Yield
With hydroxylamine hydrochloride Erwaermen des erhaltenen Oxims mit Essigsaeure und Acetanhydrid und Hydrieren des Reaktionsprodukts in Aethylacetat an Palladium/Kohle.;

water (7732-18-5) + 1-(2,5-dihydroxyphenyl)-2-aminoethane hydrochloride (88440-94-2) + K3 + NaHCO3 → indol-5-ol (1953-54-4)

[4-(benzyloxy)phenyl]hydrazine (51145-58-5) → indol-5-ol (1953-54-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / methanol / 3 h / Heating 2: MeOH / Pd/C / 20 °C / 760 Torr View Scheme

5-Hydroxy-2-coumaranone (2688-48-4) → indol-5-ol (1953-54-4) + phenyl-n-hexyl halide

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent / NH3 / tetrahydrofuran 2: BH3 / tetrahydrofuran 3: aq. NH3, air / methanol View Scheme

Homogentisinsaeureamid (5663-54-7) → indol-5-ol (1953-54-4) + phenyl-n-hexyl halide

Conditions	Yield
Multi-step reaction with 2 steps 1: BH3 / tetrahydrofuran 2: aq. NH3, air / methanol View Scheme

4-nitro-phenol (100-02-7) + PtO2 → indol-5-ol (1953-54-4)

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 (1953-54-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole (106792-38-5)

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%

indol-5-ol (1953-54-4) + methanesulfonyl chloride (124-63-0) → 1H-indol-5-yl methanesulfonate (128810-31-1)

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 (1953-54-4) + tert-butyl (1-benzyl-7-methyl-2-oxoindolin-3-ylidene)carbamate (1568924-02-6) → C29H29N3O4

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 (1953-54-4) + C15H13BrF3NO3 → tert-butyl (2-bromo-6-((8R,9S)-7-oxo-9-(trifluoromethyl)-3,7,8,9-tetrahydropyrano[3,2-e]indol-8-yl)phenyl)carbamate

Conditions	Yield
With C32H28F6N4O3 In dichloromethane at -30℃; for 35h; Friedel-Crafts Alkylation; enantioselective reaction;	99%

indol-5-ol (1953-54-4) + N-(2,5-dichloro-4-oxo-2,5-cyclohexadien-1-ylidene)-4-methylbenzenesulfonamide → (S)-N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)-4-methylbenzenesulfonamide

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 (1953-54-4) + N-(2,5-dichloro-4-oxo-2,5-cyclohexadien-1-ylidene)-4-methylbenzenesulfonamide → N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)-4-methylbenzenesulfonamide

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 (1953-54-4) + C13H9Cl2NO3S → (S)-N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)-2-methylbenzenesulfonamide

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 (1953-54-4) + C13H9Cl2NO3S → (S)-N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)-3-methylbenzenesulfonamide

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 (1953-54-4) + N-[2,5-Dichloro-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-benzenesulfonamide (102117-89-5) → (S)-N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)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 (1953-54-4) + C16H9Cl2NO3S → (S)-N-(2,5-dichloro-4-hydroxy-3-(5-hydroxy-1H-indol-4-yl)phenyl)naphthalene-1-sulfonamide

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 (1953-54-4) + 1-iodo-butane (542-69-8) + carbon monoxide (201230-82-2) → C13H15NO2

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%

indol-5-ol (1953-54-4) + 1-iodo-propane (107-08-4) → 5-propyloxy-1H-indole (147405-80-9)

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

indol-5-ol (1953-54-4) + di-tert-butyl dicarbonate (24424-99-5) → 5-indolyl tert-butyl carbonate

Conditions	Yield
With zinc diacetate at 50℃; for 17.33h;	98%

indol-5-ol (1953-54-4) + tert-butyl (1-benzyl-6-chloro-2-oxoindolin-3-ylidene)carbamate (1426931-83-0) → C28H26ClN3O4

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 (1953-54-4) + 2-(2-nitroethenyl)thiophene (874-84-0, 34312-77-1) → (S)-4-(2-nitro-1-(thiophen-2-yl)ethyl)-1H-indol-5-ol

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 (1193-21-1) + indol-5-ol (1953-54-4) → 5-(6-chloropyrimidin-4-yloxy)-1H-indole (630126-16-8)

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;

indol-5-ol (1953-54-4) + ethyl bromoacetate (105-36-2) → ethyl 2-((1H-indol-5-yl)oxy)acetate (53232-66-9)

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 (1953-54-4) → 1-(fluorosulfonyl)-1H-indol-5-yl sulfurofluoridate

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 (1953-54-4) + tert-butyl (1,3-dioxo-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ylidene)carbamate → (S)-tert-butyl (4-(5-hydroxy-1H-indol-3-yl)-1,3-dioxo-2-phenyl-1,2,3,4-tetrahydroisoquinolin-4-yl)carbamate

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%

indol-5-ol (1953-54-4) + allyl alcohol (107-18-6) → 3-allyl-5-hydroxyindole

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%

indol-5-ol (1953-54-4) → 2-amino-5-hydroxybenzoic acid (394-31-0)

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%

indol-5-ol (1953-54-4) + 4-fluorobenzaldehyde (459-57-4) → C23H17FN2O2 (1228150-85-3)

Conditions	Yield
With cerium(III) chloride heptahydrate at 20℃; for 0.0333333h; neat (no solvent);	96%

indol-5-ol (1953-54-4) + 1,2,3,4-tetrahydroisoquinoline (91-21-4) + fluorenone imine (4440-33-9) → 3-(2-(9H-fluoren-9-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-1H-indol-5-ol

Conditions	Yield
In neat (no solvent) at 90 - 100℃; for 44h; Sealed tube;	96%

indol-5-ol (1953-54-4) + N-methylacridinium iodide (948-43-6) → 9-(5-hydroxy-1H-indol-3-yl)-10-methylacridinium iodide

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%

indol-5-ol (1953-54-4) + propargyl bromide (106-96-7) → 5-(prop-2-ynynloxy)indole (153969-91-6)

Conditions	Yield
With caesium carbonate In acetone at 20℃;	95%
With caesium carbonate In acetone Ambient temperature;	87%
With potassium carbonate In toluene Heating;

indol-5-ol (1953-54-4) + (2-nitroethenyl)benzene (102-96-5) → 5-hydroxy-3-(2-nitro-1-phenylethyl)-1H-indole

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;

indol-5-ol (1953-54-4) + 4-methoxy-benzaldehyde (123-11-5) → C24H20N2O3 (1228150-84-2)

Conditions	Yield
With cerium(III) chloride heptahydrate at 20℃; for 0.0333333h; neat (no solvent);	95%

indol-5-ol (1953-54-4) + sodium 1-(tert-butoxycarbonyl) azetidine-3-sulfinate → tert-butyl 3-((5-hydroxy-1H-indol-2-yl)sulfonyl)azetidine-1-carboxylate

Conditions	Yield
With iodine In methanol at 20℃; for 24h; regioselective reaction;	95%

indol-5-ol (1953-54-4) + 4-nitrobenzaldehdye (555-16-8) → 3,3''-((4-nitrophenyl)methylene)bis(1H-indol-5-ol) (1027786-80-6)

Conditions	Yield
With benzenesulfonic acid In acetonitrile at 20℃; for 0.166667h; Sonication;	95%

Upstream product

• 1006-94-6 5-methoxylindole 
• 5594-91-2 1H-indol-5-yl acetate 
• 21598-06-1 5-hydroxyindole-2-carboxylic acid 
• 1215-59-4 5-benzyloxy-1H-indole 
• 120-72-9 indole 
• 15566-30-0 5-benzyloxy-2-nitrophenylacetonitrile 
• 100-22-1 N,N,N',N'-tetramethyl-para-phenylenediamine 
• 80792-63-8 5-Hydroxyindole radical 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 2688-48-4 5-Hydroxy-2-coumaranone 
• 22424-58-4 5-benzyloxy-2-nitrotoluene 
• 144104-59-6 1H-indole-5-boronic acid 
• 269410-24-4 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 5594-91-2 1H-indol-5-yl acetate 
• 51086-08-9 5-(2-propenyloxy)indole 
• 134792-60-2 1-(2-propenyloxy)indole 
• 4350-09-8 L-5-HTP 
• 118553-31-4 2-(Benzhydrylidene-amino)-3-(5-hydroxy-1H-indol-3-yl)-propionic acid ethyl ester 
• 128810-31-1 1H-indol-5-yl methanesulfonate 
• 153969-91-6 5-(prop-2-ynynloxy)indole 
• 3414-19-5 5-hydroxy-1H-indole-3-carbaldehyde 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 80792-63-8 5-Hydroxyindole radical 
• 100-22-1 N,N,N',N'-tetramethyl-para-phenylenediamine 
• 210160-43-3 5-Octyloxy-1H-indole 
• 147405-80-9 5-propyloxy-1H-indole 
• 210160-44-4 5-(1-naphthylmethyloxy)indole 

Relevant articles and documents

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Visible-light-promoted aerobic oxidative hydroxylation of arylboronic acids in water by hydrophilic organic semiconductor

A green and sustainable catalytic system was developed based on perylenediimide (PDI) organic semiconductor for the aerobic oxidative hydroxylation of arylboronic acids in aqueous solution with visible light. By using PDI-SN, a hydrophilic organic semiconductor, which can activate oxygen to produce superoxide radicals in aqueous solution, this reaction proceeds under ambient conditions: water as the solvent and air as the oxidant, giving various phenols as products with high yields. In contrast to methods using organic solvents, this novel process has the potential of green industrial application.

Diaryliodonium Salt-Mediated Intramolecular C-N Bond Formation Using Boron-Masking N-Hydroxyamides

Intramolecular aromatic C-N bond formation reactions using electron-rich aromatic tethered boron-masking N-hydroxyamide as substrate were realized. These new C-N bond formation reactions involve the in situ generation of a diaryliodonium salt by treatment with hypervalent iodine, deborylation by base treatment, spontaneous N → O acyl migration, cyclization, reductive elimination, elimination of benzoic acid, and tautomerization to indole formation. Hereby, we obtained highly functionalized electron-rich indoles and quinoline in practical yields.